Beautiful, Rich And Still Single – I Wonder Why?

San Francisco TransvestiteMy tennis buddies and I decided to arrange a late-night tennis match from 8pm-10pm and go out drinking afterwards.  Whichever doubles team loses pays for beers all night long.  It's a good system that brings out the competitiveness and trash-talking in us.  Besides, we feel less guilty drinking heavily if we exercise first!

My partner and I lost this time around and started buying a round of drinks when an attractive girl came up to me at the bar and said, “You have very nice, large incisors!”  She beamed me a smile.

Why thank you very much,” I responded.  “But what's that?” I glanced at my pecs, guns, and tummy.

Your incisors are your upper four front teeth.  Hi, my name is Cynthia and I'm a 4th year dental student at UC San Francisco.

Well hello Cynthia, and thanks!  I try to floss twice a day and keep em sharp.  What would you like to drink?

As far as pick-up lines are concerned, this one's pretty good, especially for a female.  She brings up something completely random, and explains in a way that shows her intelligence and occupation!  Women generally just smile or send winks if they're interested, at least that's from my experience.

Cynthia was aggressive and showed a lot of personality.  She had wavy black hair, size 0 skin-tight black pants, and a matching soft leather jacket.  Around her shoulder hung a Chanel bag with an interlinking gold chain strap.  Of course, no outfit would be complete without Manolo 3-inch heels.  Her skin was smooth and unadulterated with marks.  I venture to guess she's the type of woman plenty of women hate.

At 27, she's clearly intelligent and isn't afraid to ask what she wants!


After downing her Moscow Mule, Cynthia told me that she hasn't been with a guy in four years. This was a surprise since she is an attractive woman with a friendly, albeit aggressive personality. When I asked her why, her response shocked me.

She said, “Well in high school and college, I didn't date anyone because I was too beautiful and good for them.”

What the….?  She didn't even say “just joking” to damper her line.  She was serious and she still thinks she's too beautiful and good for most men.  At this point in time I'm thinking to myself, “Is she one of those crazy ones?  Get me outta here!

Cynthia then rambled on about how she was really focused on dentistry school and trying to get into a post grad program at Johns Hopkins or Harvard.  “No time for boys, but I'm making an effort now!”  Fine, I can admire that type of focus and dedication to one's career.  It takes guts to be so blunt.

I talked to her for 15 more minutes, gave her a hug, and told her I had to catch up with my buddies.  She slipped me her number before I left and walked out to her new $48,000 pink Mini Cooper and drove away.  Wait a minute….. I thought she was still a dental student?


Cynthia is a Princess now because she does look good and gets a lot of attention.  But, guess what happens over time?  If she keeps up her attitude and incredible sense of self-worth, no guy will ever want to be with her for the long term.  She'll be 35 years old, and still single because guys will no longer put up with her and date someone younger.  Sure, Cynthia might be fun for a one month fling, but after that, forget about it!

It's funny how women are predisposed to going out with guys older than them.  Yet, if a woman keeps this mentality, she has less men to choose from as she grows older.  Meanwhile, the younger man who was brushed aside for his immaturity gets a larger and larger pool to choose from.  Don't hate men because we go after younger women.  We were trained by women through rejection!

During our conversation, Cynthia actually had the gumption to wonder why she was still single.  I almost shit an internal brick, but smiled and shrugged like a sedated patient .  In 5 years, there's a good chance Cynthia is going to be still single with at least a  great career in dentistry and a lot of money.  Will she have a man wealthy enough to keep up with her $3,000 dollar purses and $800 dollar shoes?  She better, or else he won't be good enough!

The lesson of this story is to utilize your assets to advance your life, but also downplay them in a humble way.  Nobody is going to want an arrogant person for long, even if she's the hottest thing on Earth.  Looks get stale and desires fade.  Guys want women who are attractive, but more importantly, who have the biggest hearts for the long run.

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122 thoughts on “Beautiful, Rich And Still Single – I Wonder Why?”

  1. Just look at all these dumb women today that really think they’re special, but are real complete total losers to begin with. And the ones that have tattoos and are overweight look like real clowns altogether. At least most women in the past were the quite opposite of today, and real ladies as well.

      1. Women Today Nothing Like The Old Days

        Most women are very different today from the past when finding love in the old days wasn’t really hard at all. Most women were very old fashioned and real ladies compared to the very awful ones that are everywhere nowadays unfortunately. Many of us single men can’t even start a conversation with a woman that we think would be very nice to meet, and then there are times when these very pathetic low life loser women will even Curse at many of us men for no reason at all. I know friends that had it happened to them as well. What is up with that by the way? And why are most women so very mean and nasty to many of us men this way? Most of you women as it is are real gold diggers anyway since you just want the very rich much older men for money, which makes many of you women real users and total losers in the first place. Very obvious why many of us men can’t find love today, now that these kind of women are around unfortunately. Now i know why our family members had it very easy when they met one another back in the old days. Sure they did, and most women were very normal at that time as well.

  2. This article bothered me. And a lot of the comments bother me! Jerking yourselves off because you are upset that you are the ones not good enough for Cynthia. Seriously, if you felt good about yourself, you wouldn’t feel the need to post articles like this. Unfortunately a lot of men are just not good enough. Why should a beautiful, devastatingly intelligent, successful woman settle for a man who is less than that? I actually sympathize with Cynthia. I get told constantly that I am pretty, intelligent, and beautiful. I would not have said out loud to someone I was trying to strike up a conversation with that I’m too good for most guys (even of it’s true!). But she’s probably right.

      1. Experienced_37_F

        She is single because she has standards! You men and I see it too much, you men think you can cheat, betray and stray in tiny forms and expect women to want to stay with you? There will always be a bigger d%*k to satisfy us if you don’t want us anymore. WE have the LARGEST pool to choose from- forever. Write a survey on that. But I know you won’t. Females will always get sex easier. You men are just constantly trying to justify your losses by publishing “research” and adding words “true” and “scientists” to attract all the insecure males who google “how to get women easy?”.

    1. This is the issue with modern women. They think they are all hot shit and deserve Christian Gray or Brad Pitt. You have a dog filter over your face. I highly doubt you are anything remotely close to the guys you want to date. Just because they will bang you, it over inflates your sense worth in the dating market. Newsflash: Even top tier guys will bang women they would never want to date or marry.

      1. They Would Really Deserve That

        Most of these women nowadays are very pathetic altogether since they now have their very high unrealistic expectations and standards, and they really deserve to grow very very old all alone with a bunch of cats when their time comes.

  3. Well now that there are so many women today that are very high maintenance, independent, selfish, spoiled, greedy, picky, and very money hungry, i Can certainly see why.

  4. Wow. I agree with a few of the other commenters…men whine about this incessently because those men are very insecure and bitter that a woman like Cynthia rejected them. The fact is that those men get what they expect and what they think they deserve a la the self-fulfilling prophecy phenom. They are alone and should be alone. Women, even unattractive weak ones, do not need or tolerate weak men. That’s real and is no different than what happens to the whiney females like this–aloneness. Our society just stigmatizes women for this more because of gender biases. I think a blind person can see that. I should clarify that not all men are this way just like all women are not. I have many male friends and fam who never run into this problem because they are real men, mature, and true to themselves– not lacking confidence. No one likes a whiner and a man who doesn’t ensure that he is a winner. Similarly, I am a Cynthia without the messed up Narcissism which is a personality disorder and NOT the result of a person’s looks or a function of their social status at all. Lumping all “10s” into this/these categories of an undesirable man or woman is irresponsible and immature. The reality is our society is changing. Women are more educated and liberated, and now we are finding out that many women outcompete their male counterparts in the classroom, board room and even the bedroom. That doesn’t go over well when we consider how marriages have been framed for years. Most married women I know that married young and settled for the “old school way” of coupling feel oppressed that they must play those old gender roles while doing everything and more that their man does as far as contributing to the marriage/family. Frankly, it is nkt fair, and we single women are weeding out those men with Chavenism deep within their veins. Personally, I chose to look for and accept a longterm, serious relationship only AFTER 30 because I needed to decelop my career and also weed out the nutcases and date enough men to determine what I REALLY want. That worked well for me, and I was able to live it up, travel, work, party, etc. freely in my 20s instead of sacraficing my youth and adventure to some man and kids. There is plently of time for that when you are old. Well, at least for me. Women in my family bare children well into their 40s with no issue (my race has higher fertility rates longer, but still). But, now, I am ready. I am a strong woman that gets alot of attention; I have always been an amazing girl and woman in many well-rounded ways I won’t bore you all with. I am currently in a fabulous committed relationship and we are about to start thinking about long term plans and kids now, but I spent many years as a 20-something bewildered about the availability of eligible men on MY level. This is something almost every woman like me that I know and read about goes through. It’s the cost of being awesome which I will take any day over a man. But the lack of men is even more pronounced for me since I am a racial minority who prefers to date within her own race. For me, literally, many men have been taken out of society and are not available to even get to know. So, no, beautiful, smart, successful women like me do not usually date men that are not similarly attractive, that have criminal records, that have little observable ambition…. When we do, we quickly learn, as I did once, that these men want us BAD but are DIRELY insecure to the point of developing erectile dysfunction and resorting to violence to make themselves feel more “Manly”. What a load of crap. Cynthia should not have said it to a stranger and been so crass, but I agree with her summation of prospects in general and her being above most men. Alot of us are…her error is not dating the men around her anyway to get a sense of what is really out there and what she likes. She said what many of us often think. The truth is the truth and sometimes hurts. Face it; it is no different than the ugly truth about men objectifying women. Stop objectifying and marginalizing us throughout society and maybe less women will become shallow bitches. This goes for the fathers of women who perpetuate all this more than anyone. My dad straight up said, “…be independent first and then wait until about 27 to start looking….don’t settle for anyone but a star.” How can I bring home an average guy to THAT!? LOL. My advice is for men to stop prejudging and to start introspection instead…..and for GOD sakes, grow a pair! Lord KNOWS we women make concessions and exceptions for our imperfect men CONSTANTLY. No one is perfect; your woman eill not be either. Maybe YOU were supposed to be strong enough to handke Cynthia…maybe even help her. That is supposed to be a man’s job….and also the secret to spirituality is real: YOU ATTRACT who you are…not who you wish you were. Man Up! My man is not perfect, but he certainly did man up…

  5. I am a bit shocked by the comments even though I’ve kind of skimmed through them. Like Cynthia, I am a bit like her, independant attractive and feisty. Unlike her I was in a relationship for 10 years but….that’s another topic altogether. I find that men are intimidated by my intelligence and looks but I think the biggest reason I’ve recently found hindering my relationship status is the fact that I live in London where there are a lot of models and actresses. I’m a part time model myself. I work in a place where it’s like a beauty pageant, there’s stunning girls everywhere. The answer is it’s a case of supply and demand, there’s too much supply and the demand is less so the girls that are 9s or 10s are ending up with guys who are 4s or 5s. If you look at the less cosmopolitan areas the reverse is true however girls like me will always choose to live in bigger cities because we’re ambitious and driven.

    1. Is it possible for a girl who is a 9, NOT to settle for guys who are 4s and 5s?

      Women are much more attractive than men overall. But don’t attractive women want to be with attractive men as well? When does the decision to sacrifice begin kicking in?

      1. A 9 with a 5

        I think the desire to sacrifice starts kicking in when we get tired of having our hearts broken by the super attractive men who cheat on us. Not saying this is always the case, but it is my experience.

        Every “hot” guy I dated either ended up cheating, or had commitment issues to begin with and never wanted to have “labels”. (Those “anti-label” guys who were 9s or 10s just wanted to get laid, so things ended quickly anyway when I wouldn’t “put out”.) However, it seems that the George Clooneys want to play the field and not settle down for ages, but if they do fall in love with a girl while they’re young, they screw it up by cheating. Happened to me, more than once. Or they end up being psychotic narcissists. Also happened to me–twice to be exact. Not true 100% of the time of course. I just haven’t found the exception.

        I usually try not to talk about my exes when I’m dating a guy, but every once in a while it comes up and I get the typical reaction: “what kind of idiot would cheat on a gorgeous woman like you, and with your sex drive?! Unbelievable!” I’m not God’s gift to man, but I’m also not a 4 either, or even a 6. I would say I’m an 8.7 in looks alone, and a 9.6 when you factor in my personality (I like math, hence the decimals!) I think I have healthy confidence, but I’m not conceited either. So I just respond, “that’s what I get for dating the Denzel Washingtons, the Malumas, and the Brad Pitts.”

        So I learned my lesson, and I sacrifice looks for a less attractive (but still intelligent and charming) man who appreciates what he’s got at home.

    2. Well just because you live in a big city does not mean you’re ambitious there’s more marketing out there yes but in a small simple City they’re also good men and women . They are are men who are committed and one to be committed. A woman with caliber intelligence Independence Headstrong Rich usually walk with their head in the clouds anyway and they look for the same and they get exactly what it is you’re looking for!

      They say that Opposites attract I’ve seen it happen before I’m not afraid of an intelligent woman I’m not afraid of a beautiful woman if that woman loves me for who I am then I worry not if you choose to live that fake life that synthetic life that’s on you never will you find a person that you’re looking for because everything is fictitious. I myself I value the woman I’m looking for to treat it with respect honesty and admiration especially if she giving it back to me myself I’m not rich I’m handsome I’m fun-loving I’m I’m a man that you would probably look past because I’m not meeting your expectations because your expectations are set so high (would you ever look down? ). sometimes the better part of what you’re looking for is,if you will excuse the expression beneath you. anyway I love some of what I read and I think it’s rather beautiful myself. But the only way you going to find that right person is to look that person in the eyes because the eyes are the mirror of the soul and from there you will find the independence of the dependency that you are looking for if you keep looking in the mirror at yourself you’ll never find it

  6. Interesting post. I have a cousin that sounds a lot like this and I can tell you so far the story doesn’t go well. She’s very good looking, constantly being talked up, it was a real pain growing up with her and dealing with my friends falling all over themselves to talk to her. Smart, has a great career. Parents made a lot of money. Nice clothes, nice car, travels the world (incidentally saves nothing at all).
    Ages 16-27 she went through guys at an amazing clip, plenty were good looking and successful. We’d ask her “what was wrong with john/Sam/bill etc?” And she’d have some little thing. Not ambitious enough (a cardiologist by the way lacked ambition). To cheap, to flashy, always working, didn’t work enough…heard em all.
    27-35 the conversations changed. There’s no good guys out there. They’re allready married or divorced. I don’t want to date a divorced guy. I have plenty of time.
    35-37 where we are now. Panic is setting in. Wants kids. Still can’t come to grips with the fact that nobody is perfect.
    I’ll let you know if the story changes and she finds mr. Perfect but it’s not looking good.
    Moral is…nobody is perfect. She’s great but not perfect. I’m awsome but not perfect. I love my wife and she’s close (pHd, beautiful and supported me through medical school) but she’s not perfect.
    To the folks that posted above that think they’re perfect and are waiting for the same…you’re gonna wait a long time and having seen the progression first hand I can tell you it doesn’t go well for women as they hit mid 30s. I’m not saying marry the first douch that comes along but open your mind and give folks a chance. Let go of some little things so you can grab the big things while you still have time and options.

    1. The modern women agenda is education and career first, then marriage and family. But it comes at a price. While you are striving to educated yourself and establish your career, your male counterparts were paring off and getting married and building their careers. To complicate things, the trend of women marrying up and men marrying down still applies. Successful career women are at the upper end of the bell curve looking for successful career men at or above the same social economic level of the curve. However, successful career men are looking at women at or below the same social economic level of the curve and the tend to look for younger women. Since 1984, more women are earning degrees than men at a ratio of 3 women for every 1 man. Moreover, the feminist movement pushing the idea “women good/men bad” and so women must be empowered and men dis-empowered has taken hold at the colleges where a women’s center is a common feature and most recently, male students lament being made to feel like rapists, misogynists, etc their very first week. There are other factors as well influencing this decline in male college graduates.
      The end result is an every increasing population of successful educated women and and an ever decreasing population of educated men. One of the side effects of this over abundance of educated women is that this educated women is now the majority over educated men in the current workforce and many of these same women are taking jobs that were formally held by men. Holding out and not settling for a less ideal man who is not as well educated/successful is laudable albeit a bit elitist. The reality is this as a successful career women ages, her pool of acceptable males shrinks at the upper end of the social/economic bell curve. Dating ratios in the 45 to 55 age range for women is 7 women to 1 man and it gets worse as a women gets older. Moreover, when men are in short supply and women are abundant, the harsh reality is that the men tend not to want to commit and marry. Mr. Perfect maybe more an ideal than a reality. Not the best prospect for our best educated and established ladies.

    2. OverExperirnced37F

      They are 99% “douches”.

      We are searching for the 1% IF IT EXISTS.

      There are awful women yes, but science shows majority of men are cheaters yet they don’t include this study do they!??! Because they need science that makes me “feel” special.

      I’m over experienced, attractive and I prefer older men but even when I was 16-25, older men did NOT want me in any way because of the clear fact alone, men are intimidated by attractive females. Age does not matter when we are “out of their league”. Not all of us women go for hot men. I would have easily settled for a nice unattractive man if he just had the confidence to talk to me or keep me.

      It’s amazing how many of you men are delusional thinking it’s US women who are the delusional ones.

      We don’t need men for babies anymore, I see the IVF world creating happy single mothers because of society with men thinking they have age to win women. Sad. So sad.

    1. I know,I’m exactly like her&when I meet a guy who attracts me once on a million years he’s involved with some cheap bimbo

  7. I grew up a shy introvert truly believing I was the ugliest duckling alive only to find out others thought I was pretty and men find me attractive. I didn’t know it then but guys didn’t approach me because they were intimidated. They were the ones who thought I was too good for them. Now that I know I’m pretty it bothers me a little when I’m complimented solely on my looks which happens too often. It implies that I’m shallow, overly concerned with my appearance and there’s nothing more to me than my looks. You see how that stereotype is naturally imposed. People think that good looking people have it easy, but thats not always the case. If anyone actually takes the time to get to know me, they’ll find a down to earth ambitious female who finds beauty in character; is attracted to maturity and wisdom; and loves for the sole purpose of loving. Most men won’t take the time, they assume I’m taken or single for a reason and this is where the aggressive behavior comes in. Then they assume I’m needy, insecure or have an ulterior motive. It’s a vicious cycle.

  8. I know this is a really old post but I happened to stumble on to this. Like the other female poster in her 30s, I actually pity Cynthia. I’m 35 and unmarried, but am seeing a terrific guy right now in his early 40s. He’s got a lot in common with me, and is so kind and intelligent. He’s a bit introverted at first, but has a great sense of humor once you get to know him better. We also have great chemistry and just enjoy being around each other. We can talk for hours and enjoy doing even the most mundane things together. For all these reasons I feel so lucky to have met him. However, I get the feeling that he’s the type of man who Cynthia would have dismissed immediately, for being a bit on the shorter side, not dressing like a GQ model and driving a reliable but not flashy car. That doesn’t bother me because I’m also not exactly a tall model either. He’s financially well off but, just frugal and not a flashy type who would want to blow that kind of money on high fashion items.

    It’s a shame she probably dismisses men like this, because she’s probably depriving herself of a great possible connection. I’m wondering if she’s still alone, waiting for the man she is “entitled” to. That would be mighty lonely. And the types of GQ models she wants are typically cads and players (I’ve dated those before too and burned out on them pretty quickly. No level of hot compensated for the endless mind games).

    I wonder what will happen when she’s older, her looks start to go and she doesn’t get as much attention. I guess that’s the silver lining to being cute, but not “hot” either. In all modesty, I think I look good for my age and I do the best I can with my appearance. However, no matter what effort I put in, I also don’t delude myself that I’ll ever be Cynthia level “hot” either, or the sexy type who turns men’s heads instantly. Since I don’t routinely get validation for looks, I’ve learned to develop and prioritize other qualities–which matter more in the long run. And getting older is actually easier for the “cute but not hot” types like me. We never got that kind of attention even when we were younger, so we can’t ever miss what we never had to begin with!

    1. Hi Christine – No post is old on Financial Samurai! I see all comments :)

      I do wonder what has happened to Cynthia. I know she went to Boston to do more studying. A fellowship I believe.

      Perhaps she will one day end up alone b/c she was too picky. Or maybe she’ll never find that true connection. Hard to say. Women like Cynthia get a lot of attention from men. I’ll find out and report back!

      1. Well, maybe she gets a lot of attention, but not the right kind that would actually lead to a relationship? All that attention wouldn’t lead to a relationship if, say, she gets it from a lot of players, and not from anyone commitment-oriented. I’m just trying to figure out how a woman who presumably gets a lot of options is still single. Or as I said before perhaps her “picker” is off.

  9. Off course, If she plays game the good times are over and she has to go. She is a good match for a short one, let us say a weekend, I spend a few hundreds and bye bye. She wanted more but played games, then she had to go. As simple as that.

  10. Interesting story. I actually went out with a woman like this, and it is a red flag a big one when she said “I am too good for most guys…etc….”. It is good to be a good looking woman, it is also good to be educated and all that, but being arrogant, materialistic is a turn off for any successful man with dignity and character, at least it is for me. I sent this woman a present for her birthday (A bonsai, flowers, a post card and a little teddy bear) I told her to come to see me for christmass to take her out shopping so she can pick something she liked, 2 days before chrismass I bought a house after she asked me to do so, she wanted a family and her name in the house. Guessed what she answered? A/ She can’t be with somebody that does not know how to give her gift. I could not believe my ears. She came for chrismass with an attitude I could not tolerate any longer, I dropped her on the spot. That was my chrismass present, the best one so far. I hope she got something good out this situation. I did, I learned to be more carefull and never again allow myself to go put with this type of woman anymore. Now i am going out with a good woman that appreciates me for who I am.
    Be confident but not arrogant, be respectfull and learn to appreciate things in life other than materials.


    1. Well, it also depends on what you are looking for in a relationship. If you’re just looking for a good time, then maybe she is a perfect match? Nothing wrong with short term fun from two consenting adults right?

  11. The story’s really sad. It’s like the first half of a bad Lifetime movie. I used to go (god it hurts to say) clubbing in the bay area well over a decade ago, and the stereotypes are eerily real and apparently stand the test of time. Luckily I come from a long line of women who married younger men. My husband’s younger than I am but we joke that he’s the “old fart” in our relationship. He’s confident and a strong person who makes it easy for me to be me. Sorry for the shmoop but it’s our anniversary this month so it’s been pretty shmoopy. Just a thought, sometimes information vomit like Cynthia’s just masks DEEP seated insecurities. I bet there’s a scary high school photo in there, braces, maybe goth…something good.

    1. Boom shucka boom shucka boom! Clubbing alright! :)

      I bet there is some scary HS photos! After all, she did go to a great college and got into UCSF, a Top 5 dental school in the country!

  12. Sam great article. I have run across a few women like this in my life. They are great to look at and look great on the arm for a month but that dies quickly as you stated. There is only so much you can put up with before you just say enough is enough are you really that full of yourself. I know a few women who think their sh*t doesnt stink like Cynthia, brings a smile to my face seeing them spend it alone every valentines day…


      You guys are such babies. You are an idiot. Not every pretty girl is some f’d up attention seeking primbo that likes to hang off the arm of some man. I have not meta man yet who has a good enough arm for me to even think about hanging off of it…. So please..stop it.

      Um, not every girl is mooning for romance. WAKE UP. Last time I checked this was 2012.

      I get chocolates from my parents and lots of flowers. I love it! Smart assured fabulous ladies do not all pine away on Valentines Day.

      I know why I am single. I do not even bother. I am not going to attach my wagon to just any old horse!

  13. Two thoughts:
    1. I heard about an embroidered sampler hanging up in a Vassar dorm. It said, “Tits sag. Wits don’t.” This woman will soon lose the advantage of youth — and she may never obtain the beauty that can come with old age, since it requires something other a gorgeous facade. Not every woman who gets married is perfect-looking; plenty of average- or even below-average-looking women are appreciated by men who can look for something besides physical perfection. That’s where the “wits” part comes in — and it ain’t just IQ, either.
    2. Will there be a post about how shallow and entitled some good-looking MEN are? If you threw that open for discussion no doubt your young female readers could give you an earful.

  14. I’m late to the game, but I stumbled on your blog from Financial Anarchist, who btw was dissing your post. I think Cynthia is a dime a dozen, at least here in NYC. I can’t believe, however, that she actually said “I was too beautiful and good for them.” That says loads about her character and upbringing. There’s a distinct line between wanting to be with someone who is your equal and lacking the humility to appreciate the other good aspects of a human being.

    That being said, a guy recently asked me why a pretty girl like myself was still single. Kind of what you’re questioning about Cynthia. Except I’m not stuck-up. I hate this question because it can make a girl think that there’s something wrong with her, like damaged goods or something. I agree with some of the insights provided by the female commenters above. To add my 2 cents, honestly sometimes being single is a choice. I’m still recovering from a break-up (2 mos.+ now) and I can’t do the rebound thing so I’ve decided not to date until I feel emotionally up to it. Just getting back into it now.

    As for my theories on the men, my experience has been that most guys who are confident to approach the Cynthias tend to be players who want to screw around. So not ideal settling down material. I’ve rarely dated someone who is my “equal” because I think a good heart, etc. can be more important than looks, education, etc. But you know what, those guys get insecure and/or lack the ambition to want the same things such as a successful career, commitment to marriage, etc. And this is why I’m almost 30 and still single. :)

    1. Hi Jeweliette,

      Wise perception of men with courage to speak to the Cynthia’s of the world. You are actually spot on. Guys who can speak to her aren’t really interested in settling down as much. They enjoy the game and have the swagger to back it up.

      Thanks for your perspective on being emotionally ready before diving in. Turning 30 is kinda a shocker but one gets over it quickly.

      What is the URL to Financial Anarchist? Never heard of it and can’t find it!

      Next time I’m in NYC I’ll give you a heads up and buy you a drink to pontificate.



    2. you are blaming others, your are single because you are another cynthia in denial. I am sure you have known a good number of good men, but you are simply “too good for them”, am I wrong?
      As far as turning 30 you should be worried, you sure don’t want to look like the grandmother of your children. Also the quality of your eggs decreases increasing the chances for genetically linked problems.

      1. And I’m guessing you’re one of the guys rejected by the Cynthias of the world so you’re unleashing your bitterness at a stranger? =P Thanks for your concern, but I have a wonderful boyfriend now and we’re both good for each other. Also fyi, everyone has differing perceptions on what’s considered “good.”

        1. No, I have had bad and good relationships, in general I am a very strong person, I learn from my experiences, I not a naive kid anymore. I have been married for 10 years with a very good woman, so I don’t have much to complain about.
          I am just giving my honest opinion about why some type of woman is still single, the answer is simple: Nobody can tolerate their bad temper and attitude for a long time.
          This type of women attract “players” because that how they come across with their bad attitude. It is good you have a wonderful boyfriend now, treat him right if you want him, just dont use him because you feel your clock is ticking. What is good or bad for you it is for you to decide, but i am sure you know that there are some good and bad universal qualities.

  15. Cynthia might just be looking for someone who can challenge her. Younger women date older men because they are more mature, educated and established. I firmly believe that a partner is someone who can make you grow as a person, hense most of my dates were 10 yrs my senior, simply because they were easier to talk to, wealth did not intimidate and confidence did not send them running for the hills. Also, people who are in professions like Cynthia need to show that they have money. I have friends in law, real estate, and other businesses and they all have to “keep appearances”. Their cars cost more than my home and their watches more than my wardrobe now.

    1. Perhaps. But don’t you think after a certain age.. eg 25, everybody has pretty much matured already?

      Men LOVE to hear women desiring to date older men 10-20 years their senior. Makes us all look forward to getting older!

      1. Hmmm….I don’t think so. Most people nowadays are really not much different than teenagers (I know I’m generalizing here big time). I do speak from experience so I guess that’s what it was for me. The people I met were all about partying, drinking, getting wasted, etc. I really never saw the sense in all that. Sure partying is nice but when it’s an every weekend thing it becomes a chore rather than a nice night out. I guess for whatever reason I just attracted the wrong crowd which is why I just moved on to older men. Stable, secure within themselves, comfortable in their own skin, and not easily intimidated. They were always easier to talk to, I didn’t have to explain myself, they kept up with current events, politics, economics, finance, etc., subjects I am really interested in so naturally I just gravitated towards them. It was “like finally, someone that sees the big picture too”. LOL!

  16. @ Bridget,
    I am in the same boat, though Im one of those women people, ehem, women love to hate. I am beautiful, I get it all the time, but beauty and brains intimidate men for whatever reason. Top that off with being a successful entrepreneur and military…….I get told I make too much money, do not need a man or I am just too smart. Lmao. I am pretty well rounded so when I go dancing I kinda sorta dominate the floor, just happens that way but the other women hate me for it. My younger brother and I went dancing and a woman he was dancing with threw her drink on me because I was “C*ck blocking” her. She then proceeded how beautiful stuck up women like me needed to leave their men alone, lol, and told my brother that I was not what he was looking for and that women like me where loose (not the word she used, rephrasing that insult) at which point I told her I was going home with him and my brother called her crazy and told her to “watch it, that’s my sister you are referring to” and she looked stupified.
    Not all of us who dress like “Cynthia” and act like her do it because we want money, seriously as Sam stated, someone who makes that kind of money would want to be with a player that can keep up ;)
    Some women are just very picky, goal oriented and know what they want in life, what do you call it when a man does it? Oh wait, we have those everywhere too! Lmao. I think Cynthia just wanted the security of knowing that if she lost it all, her partner has more than enough to keep her going.

    1. Awesome story! Thanks for your perspective.

      Are you with someone now?

      I love the beautiful and wealthy woman, so don’t worry! If you’ve got a good heart, then you have the pick of the litter!

      For Cynthia, she came across too strong for me to ever know.

      1. Aww! Thanks! Not at all actually, I am happily single. I’m starting my masters this year so I will be very busy. I really do not understand at all the stigma of “it’s all downhill after 30”. Nothing extraordinary happened to me when I turned 30. I still had all my hair, no fairly came to my window to warn me of impending doom, LOL, and my circumstances are didn’t change. I think it is just a cultural thing.
        Hahaha, okay I’m a softy for hungry and homeless people. Somehow they always find me, and no I don’t turn them away. I don’t give out money, but I am very generous with buying them food. A group of my college mates once up and left a rather nice restaurant because a homeless man came in and they told him that “they didn’t serve his kind”. We were furious and as the waiter came with our food we left telling the server that “our kind cannot eat here”. We went to a restaurant across the street and bought the man a nice meal, the poor man couldn’t use the clients bathroom but they gave him full use of the employee’s bathroom and lounge area clean up. No one in our network ever steps foot in that restaurant, among our friends it has been “blacklisted” permanently.

  17. I have mixed feelings when I read this — and even more when I read the comments. Truthfully if she hadn’t said she was too good for every guy when she was in high school, I actually wouldn’t have thought this woman had any immediate glaring flaws.

    Dating actually isn’t that easy, even if you’re beautiful, intelligent, and successful. I don’t own Chanel bags or a Mini Cooper like Cynthia, but I dress well. I’m very attractive by most people’s standards (and I mean that in the most humble way possible), and I graduated with honours from my BSc. I have an excellent job with a good income (though not that of a dentist.. well, not yet). So where are the men?

    I did have one semi-successful 4yr relationship that ended nearly a year ago — he cheated on me and left me for a girl that was “less intimidating” (his words). Since that ended, I’ve been going on dates regularly but all the men I see, be they student or professor, bartender or doctor, age 22 or 32, are “not interested in something long-term right now”.

    Frankly, I sympathize with Cynthia. My latest flame told me he couldn’t believe I was interested in him because he was certain I would go for “those GTL-type guys” (yeah, as in GTL from Jersey Shore). He dumped me a month later, claiming to not yet be over his last girlfriend. Being an educated, attractive, late-20’s woman certainly has its perks, but so far, easily finding Mr. Right isn’t one of them.

    1. Hi Bridget,

      Thanks for your perspective. I’m glad you have the confidence to think of yourself as very attractive by most people’s standards and it doesn’t seem like you are having trouble getting dates. Perhaps you’re just unlucky, or maybe there might be something that bothers the guy that you are not aware of? Most attractive people I know never have to say they are attractive and humbly put themselves down instead.

      Nobody is perfect, but everything is pretty rational in the long term. No beautiful, kind hearted, funny woman remains single for very long. If one doesn’t have all those attributes, then maybe one has to expect different things.


      1. “No beautiful, kind hearted, funny woman remains single for very long,” then what about me, Sam?

  18. Sam you’re quite the lady magnet eh? This sounds eerily similar to one of your gal pals you ran into a few months back. She was too pretty and now is having a hard time finding a guy. SF sounds just as bad as LA! However, haven’t been in the scene for awhile so what do I know. Fun post!

    1. Haha, not really. There are some parallels with my other lady friend who is now 36, but she was demur and much less full of herself. Her shyness was misinterpreted for being stuck up. Glad you enjoyed the post as much as I enjoyed writing it.

  19. @Arthur Garcia

    Great point Arthur. Funny, I know a girl, very grounded and pretty easy on the eyes. I called her cute once and she responded, “Don’t you know never to call girls cute?” I can’t remember the entire explanation, but it was something to the effect of girls rather hear pretty or beautiful rather than cute. Almost like being called a nice guy instead of handsome or good looking?

  20. My best friend was a Cynthia when I met her. It was really hard to get to know her better as came across extremely shallow and spoiled. Its fascinating to hear that there is a whole slew of them out there. It also breaks my heart that people have this type of attitude.

    My best friend has learned humility over the last 4 years but flashes of Cynthia still pop up once in a while. Its hilarious to see that side of her now. I agree that focusing on a career is important, but sometimes you miss out on the greatest opportunity of your life because you assume that you are too beautiful for it.

  21. Sam, I couldn’t tear myself away. This story was too good. I take it you’re not going to call her :). That type of conversation would be a turn off for anyone except and exceptionally narcissitic guy.

  22. Lots of great posts on relationships the past few days!

    As many of your readers have said, Cynthia’s education and lifestyle is likely funded by Bank of Mom and Dad. Maybe she feels that the guy she brings home must also meet the expectations of her parents, if they’ve repeated told her that she needs someone “good enough” for her. Sometimes, girls get caught up looking for “Mr. Perfect” before they realize he only exists on Grey’s Anatomy, or some other tv show.

    Or maybe she is just really full of herself and thinks she is being confident instead of arrogant. You sure you don’t want to give her a call and find out? ;)

    1. Haha, sure, why not. One can always have more friends.

      I just realized something. She went to a prestigious undergrad, and is at a top 10 dental school in the country. She is going to be an MD, so can we really blame her for wanting a man that is equally as intelligent, and has the same earnings power, and is decent looking as well? After all, she busted her butt to get to where she is.. anything less in a partner would be disappointing!

  23. Great story and it is so true. Her self-esteem is too inflated for the reality that we all live in. She does need to tone it down a bit and If I were single I could help her get a reality check.

  24. What’s up with the ladies in SF?! I don’t completely agree with Sandy since I’m mostly from the West Coast and not shallow. (I hate shopping and am just fine wearing Keen sandals all year). But there’s something going on with the ladies you’re meeting in the Bay Area. This is very similar to your post about a female friend of yours who’s 35, still gorgeous, but single because she was too aloof. I’d almost say, give the girl a call and find out first hand what’s really going on. Then you can report back and give us the real scoop!

    1. Perhaps it’s just my circles? I donno. I empathize though. She’s at one of the best dental schools in the world and has high expectations. If she works that hard, she should expect her man to do the same if not more.

  25. Money Reasons

    Self-perception is an odd thing. I’ve seen both very beautiful girls and very plain girls act the same way. The plain girls really have a hard time, but usually settle once reality strikes when they are much older. Oddly some of the most beautiful women at work get so involved in their career, that they don’t date… I think if you are too beautiful and sexy, guys are too aggressive perhaps and after getting constantly hit on perhaps some of the very hot women shutdown that part of them?

    Relationships do require a lot of time and learning the other individual, so I guess I understand why a career woman doesn’t want to get involved.

    Life choices I guess… Still it’s kind of sad…

  26. It seems like part of the problem is that beautiful women like this get treated differently by men, so it tends to affirm their self-inflated attitude.

    I mean, a good-looking woman approaches a guy in a bar, says some pretty obnoxious things about how great she is, and the guy just listens without contradicting anything she says (like a sedated patient), and even gives her a hug goodbye and accepts her phone number, making her think, wow, he must really like me enough to give me a hug (because I’m so great and good looking and personable).

    If this was a not-so-good-looking woman, she would have had plenty of experience being dismissed by men for referring to herself in such high praise, so she would have realized by this time in her life that such egotistical behavior is appalling.

    But guys tend to be dishonest to beautiful women and allow them a certain leeway in social situations.

    Even though you were thinking almost immediately after starting the conversation that this lady is crazy and I need to get out of here, you didn’t say anything to her about your feelings and even talked to her for 15 more minutes.

    That’s probably because you enjoy the social experimentation of seeing where she is coming from, but this same thing likely happens to her all the time, she says obnoxious things to guys about herself, and they don’t say anything contradictory and just notice her designer outfit and good looks, so it reaffirms her behavior.

    Guys lie to good looking women, and it fills them with a sense of self-grandeur.

    If you would have been as honest to her about your feelings as you were with us in this article, it may have actually helped her realize that her behavior is objectionable and off-putting to say the least.

    1. I give all women hugs if they are so inclined, just like I shake all men’s hands if they are so inclined.

      I see your point. I accept it is my fault for her being. At least I was being nice!

      1. There’s a lot to be said for being nice. It’s one of my favorite qualities in people.

        Of course, I wouldn’t go so far as to say that it’s your fault for her being,
        as each person is ultimately responsible for their own behavior.

        I’m just making a general argument about how social influences can trigger
        certain behavioral tendencies in social situations.

        However, I would say the same is true for the reverse sexes, that good-looking
        men get treated differently by women, and it influences their behavior with

        Anyway, it would be an interesting experiment to try to be honest about
        what you’re thinking to someone in this situation.

        You could say something like, “You know, the reason you may have trouble
        finding relationships is because you come across as a little full of yourself…”

        That could lead into an interesting conversation.

        1. Interesting view Max. My guess if Sam gave her a dose of reality like you suggest, she would have aggressively tried to go home with him. No guy would give her a honest view of herself and if her self esteem got checked, she would probably want Sam more to validate herself.

  27. Growing up/Living on Long Island I encounter this type of woman on a daily basis (except they aren’t really hitting on me lol). I even work with a few lol. It is the kind of girl where you can never provide as well as Daddy so you can’t live up to him in her eyes/tastes.

    I am not sure why but everyone is saying don’t call…CALL HER and have that month long fun fling!

    1. Sandy @ yesiamcheap


      Alright I’ll agree with Evan. These girls exist in California, Long Island, and Jersey. They cluster somehow. You can usually see them coming in herds:

      1) Fake tan
      2) Fake boobs
      3) Hair extensions (no guys, it’s not real)
      4) The IT bag or shoe of the moment and @youngandthrifty is right. It’s the red bottom LB’s now. Keep up guys
      5) Readily identifiable designed clothing labels
      6) Drink in one hand, cell phone in the other

      Men, if you see these women, they don’t want you. They want your bank accounts. I Ladies, don’t be this woman. Although, if you’re not this woman, and see a man that you would like to go after, offer an offhand comment or compliment, smile like you mean it, and strike up a conversation…and make sure you box out the other women waiting in the wings to strike.

      Good husbands are hard to find.

  28. I agree with Sandy, there are many girls like this on the West Coast.

    About 50% of the girls you see in Vancouver clubs in Granville street pretty much fit this description.

    Oh wait, they also have fake tans and fake boobs. ;)

    Well, has anyone thought that perhaps Cynthia is self conscious? Sometimes people project arrogance and over-confidence when they are actually really insecure (especially since she has to TELL people she thinks shes single because she’s too pretty). Who knows, she may be going home to cry and gulp back a bottle of wine because you haven’t called her yet.


    1. There must equally be as many girls like this on the East Coast as well! Come on now. Maybe there are more fake tans out East Coast dang, it’s cold for 5 months of the year there!

      Smart guys know how to play to a woman’s self-consciousness by buttering them up. We have a secret handbook on how to deal w/ various types of women. However, I cannot reveal the man code.

      Maybe they were Louboutins!

  29. Run. For. The. Hills.

    Simple as that.

    Really, who wants to try to keep up with her expensive tastes and self-absorbed approach. The looks fade, and the reality is that most guys aren’t going to care how successful she is in her career anyway. Hopefully she doesn’t extact money out an older guy who feels pressure to buy her things and keep her happy.

    1. Yeah, but it’s not like we’re in a serious setting or anything. Just a bar for shits and giggles, which is why meeting anybody at a bar has such a negative stereotype!

  30. Sam, you should write detective novels. You’re pretty observant.

    If I had a few beers though, I don’t think I’d be holding my tongue.

  31. Sandy @

    You’re on the West Coast where shallow woman are cloned. I’m sorry, but a reasonably intelligent woman who wasn’t so full of herself wouldn’t be single for long.

    And on being aggressive, I believe in getting what you want. Like I told a friend, you won’t find a husband just sitting there on the couch at home for you with a nice shiny bow. You have to get what you want!

  32. Wow… Look, I’m as allergic to high maintenance as the next guy, but there are some rough comments on here! There are a lot of positives going on here. I don’t like the excessive spending, but the lines about her being better than most of the guys in high school and undergrad degrees… well isn’t it kind of factually correct? Wouldn’t most women in dental school have been in the top 2% of their high school class in terms of brain power? One could also guess she comes from some money, and you describe as being in the top 10% or so in terms of physical attractiveness. Study after study shows that while we hate to admit it, we usually end up with someone similar in stature and physical attractiveness to ourselves (not me, I batted way out of my league, I’m the outlier). So isn’t she just being honest when she says most high school guys and undergrad guys aren’t really the calibre she intends to marry?

    I’ve dated several women who gave off worse first impressions than this! She definitely appears to have her drawbacks, but a girl who is that smart, with that much confidence and drive could be a catch for a very strong-willed partner that could “hold their own.”

  33. Okay, time for a woman’s perspective :)

    When I was 17, I would have hated her. I’m short, athletic, pretty, and smart, but at 17 I didn’t know that. I would have constantly thought any man I was with was more interested in her than me. Dumb bimbo.

    When I was 27 and done with grad school, I still would have hated her. This time because she’s clearly smart AND pretty. Not a bimbo, but clearly a home wrecker in the making.

    At 37 (okay, I’m 38), I feel sorry for her. Because at 38, I have a great career, I’m still short, athletic, and pretty (with maybe a wrinkle or two), and I’m happily married with a family. She’ll never know the feeling of true love because she’s too in love with herself. Her awesome career will be little comfort when she’s 57 and still single.

    1. Good to read some female perspective here! So the question is, what if you are 38, single, and no family? Do you still hate or pity her, or root for her to….. find her guy or find nobody and join you?

      1. I’d root for anyone to be happy and fulfilled in life. But that said, if I were the person I think I am now, but single and no family, I’d probably still feel sorry for her. I can’t imagine she has genuine friends and relationships, because it’s a competition of looks and material possessions, which turns into envy and distrust.
        I’d feel sorry for her if she hadn’t figured out that happiness can’t be bought – and you have to be willing to give as much of yourself honestly as you expect in return. I’m not saying money is evil (quite the contrary), but money without a source of fullfillment is empty.
        Wow…I’m so not this deep or serious most of the time! Going to go get a beer and chill out now :)

  34. Did she happen to write her phone number on an old ATM receipt showing her excessively large balance. That’s my favorite “pickup” line…
    Cynthia reminds me of a girl I knew in college, only my story was cut short. She aggressively approached me to dish out a compliment. She then asked “what year are you?” “Sophomore”, I replied. “Oh nevermind. I thought you were a junior.

    1. Oh wow, that is a GREAT pick up line regarding the ATM balance receipt!

      Thanks for the tip! Haha

      Women should see that men date younger because of women like you mentioned!



        You guys sound like a gaggle of feckless boobs. Grow a set and stop all self assauging & tired platitudes.

        I am a gorgeous and I mean like “HOLY SHIT”….JAW DROPPING”, STUNNING. I also have an ivy masters degree and a successful business. I own 2 homes( paid in full thank you very much),and *drumroll* and am absolutely in love with myself.

        Can’t remember a time when I did not truly love being me. I am only 25.

        I never bother to date anyone. I am too busy and happy by myself. Life is too short to waste on some boring man who hasn’t a real clue about much.

        I have found that( my dad is thankfully able to be excluded from this pitiful group)that 999999.9( bar over last nine) % of the male population is pretty worthless.

        Men for the most part are pigs underneath it all. Yuch! I am not a man hater. I just am not impressed by what I see on a daily basis.

        Am I wrong to expect a man to bring all the same things that I have to offer to the table. he had better be Hawkings smart( I am),super wealthy and generous of spirit,interesting,galant,
        super motivated,attentive, but never clingy or overly inquisitive about my personal life,always behave like a gentleman,have a great sense of humor,be super respectful of himself and others,
        and be as pretty as me. Calm. He must be a calm person. I do not like outbursts or a panicky Petes.IF IT IS NOT DYING OR ON FIRE DON’T BE A HYSTERICAL DRAMA QUEEN.

        If he is not wealthy to be considered he needs to be seriously involved in something like saving animals,or building hospitals in poverty stricken countries…You get the picture. HE NEEDS TO BE EXCEPTIONAL!!!

        I know I am probably going to be single for a looooong time if not permenantly. I am ok with that. I would rather spend my time enjoying my own company then spend one second of it listening to some snooze factory yammer on about his boring exsistance.

        You are all just trying to make yourselves feel better but you know damned well if you had a shot in hell with a kick ass female like me you would be super jazzed. GET REAL!

        To the “women” with the family I am happy for you…genuinely, but do not kid yourself if I wanted to be married I very easily could be…You just have lower standards. Sorry hun, but you do.

        I am not lonely or unloved. Yes, I love myself but not for my great looks. I am aware of them but they do not rule my days! I love my mind and heart more.

        There are tons of successful ,interesting and fantastically gorgeous( inside and out) women in manhattan..Where are our counterparts? Where is the young man that looks like Matt Dillon at 25,with the heart of gold,and a bank account to match. I have not seen an attractive man in years!

        Maybe all the gorgeous guys are off building hospitals in Kenya or something. I sure hope so!

        I am so over it…LOL

        1. hows life?
          still single.
          i am the guy you described that u want.
          but i would never date u in a million years.
          just look at ur attitude.
          pathetic child

  35. Good observations for a man: Chanel bag, Manolo shoes, size 0 pants (how did you figure that out?) and so on. Usually men cannot distinguish Chanel from Walmart brand. Anyhow… I had a friend like this girl. She ended up with a sugar daddy who treated her like a piece of furniture. She moved on to a self-proclaimed millionaire who was addicted to porn. We are not friends anymore, so I don’t know where and with whom she is now. Alone perhaps? Too sad because she missed a lot of nice guys along the way.

    1. I guessed on the pants given I know many size 0 women. The bag was too obvious and in my face. The shoes, maybe they weren’t Manolos, but if not, definitely something similarly pricey.
      I have a good memory for prices.

      Your friend got what she want though, so that’s good yeah?

    2. Sounds like the women in college going for their MRS degree instead of an MBA like the rest of us!
      But sad in the end, when you think about it. I want to live my life thinking about what they’ll say at my funeral. Loving, caring, generous, and kind will mean more than listing off my material belongings.

  36. Have you heard that less people are getting married, according to the news! She is keeping herself unavailable and will probably remain unmarried. She will then grab the first rich guy and bleed him dry!

    I wonder how she supports her lifestyle? Maybe she has indulgent parents who contribute to her arrogance. Beautiful women go for older guys (not me) because they will indulge them with their money. I am thrilled that my money makes me more attractive in my old age (sic)! It makes me glad a have a good wife!

  37. Cynthia may have a point of being too good in high school (and possibly college) – why should she waste her time when she feels she could do better? Now that she’s out meeting people from all places (assuming that you were not her first ‘victim’) she shouldnt have such an attitude. Not every guy in the bar is looking to play some game and could actually be interested in the things she was interested in, as well as appreciate her looks – unfortunately, while her surroundings have changed, her attitude has not.

    Any guy would go for someone who looks almost as good as her, but does not let everyone know how much better she thinks she is than everyone else. Money helps as life goes by, but it does not fill the deafening silence of loneliness.

  38. Haha, great post for the Wednesday doldrums. I don’t run in that circle so I don’t know anyone like Cynthia. I guess my incisors are not that nice. Hopefully she’ll land a sugar daddy, that seems to be the only way she’ll find someone. Move to LA to hang out with movie stars?

  39. She sounds pretty full of herself lol. There are definitely women out there who are totally obsessed with their looks that they forget to look within and grow as a person. People that are too focused on material things and appearances can easily become very selfish and that is a major turn off. Perhaps Cynthia just needs to find a guy who’s as obsessed with his looks as she is with hers and maybe they’ll hit it off!

    1. You are probably right Sydney! The same attract in this case! Or maybe, some really insecure ut well-to-do guy who never has had a woman in his life will put up with her. Possibly!

  40. Arthur Garcia


    Great post! I liked the story and the moral at the end. It is nice to see you trying different post styles.

    As far as ladies go, I am a firm believer you should go for cute not HOT! What’s the difference? Cute girls get “normal” levels of attention so they’ve had time to develop other aspects of their personality – humor, values, interests, etc. Hot chicks are actually crippled, in my opinion, since everything has been made easier for them, just because they look nice!

    In addition, cute girls can become “hot” – change of clothes and a cute haircut. But they are not afraid of doing yard work, painting a room, hiking, etc.

    1. Hi Arthur – Thx for your message. If you click the “Relationship” category, you’ll see some previous attempts. It’s fun!

      Good point on cute vs. hot. I have to agree. Although, if you had a choice between hot and cute staring you in the face, it might be hard to choose!

    1. Hahah, that’s what I was wondering! With dental school at $45,000 a year, she must be loaded right?

      Of course her lifestyle is funded by the Bank of Mom and Dad. Princess, remember?

      Please kick your husband’s ass and start doing more around the house especially since you earn 2/3rd of the household income! Do it!

  41. Remember my personal finance lesson “Don’t date girls with small dogs they carry in handbags.”

  42. Dave @ DebtBlackHole

    I’m so jaded I’d probably think she was a hooker at first (or, at the very least, a stripper).

    Have you noticed that the more “beautiful” a person is the greater their need to have constant validation of their “beauty”? I can’t even imagine the extreme self-esteem issues that age (and gravity) must bring to people like this.

    Keeps the plastic surgery industry going and going and going…

    1. Haha, I guess that is a possibility b/c what hot woman hits on a guy right?

      Yes, I have definitely noticed the more attractive a woman, the more she will ask, “how do I look?”. Kinda weird. Maybe because she’s always had so much attention and been told she is attractive, that once it stops, the security blanket goes away?

      1. No, we are just conditioned since very early on to believe that the primary source of value is our looks … so we become very sensitive to keeping that value high. Makes me sad

    2. Money Infant

      The first thing I thought was gold digger. Still in school, but $3000 purses and $48,000 car? Or maybe her parents are rich and she is their little princess?

  43. I think you are dead on in your prediction.
    Personally I have not met anyone like this, but, I have likely seen them – especially in the days I used to frequent pubs and bars.
    To be honest, I thought this article was going to move toward the fact a lot of guys might be intimidated by her beauty and perhaps they lack the self confidence to approach her. Glad it didn’t go that route!

    1. I think after a certain age for guys, we just don’t give a crap and have no self esteem issues whatsover. I admire Cynthia for her aggressiveness, as women just aren’t that aggressive pursuing what they want. I have two female friends in particular who are very nice and attractive, but they let the guys they liked go b/c they were too shy, and now they are alone.

      Go for what you want, just be balanced about it!

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