If You Were Broke, In Debt, Or Unemployed Would You Settle For A Less Than Ideal Partner To Save You?

Stripped down bike with nothing leftGiven older women refuse to talk to me, I decided to have a couple conversations with two lovely, younger women about personal finances one night out of town. Nothing gets a woman going like a man who can talk about derivative investments!

Woman one – let’s call her Amanda – is in her mid 20s and is currently going through a quarter life crisis. She recently broke up with her boyfriend in Los Angeles and moved back to Miami to be closer to family and childhood friends. Amanda is currently unemployed, has less than $2,000 in savings, and has roughly $50,000 in credit card debt thanks to a lavish lifestyle she and her ex led for two years. She has a marketing job offer in Chicago from one of her male suitors, but she’s putting it on hold as she really wants to find something in Miami. Amanda comes from an upper middle class family who own multiple properties around the world. Despite her parent’s ability to financially support her, Amanda says she doesn’t want to rely on her parents for anything except for moral support.

Woman two – let’s call her Victoria – is in her early 30s. She’s a manager at a large consumer products company and pulls in a low six figure salary in San Francisco. Victoria can financially support herself and is currently dating a wealthy boyfriend. She has always been the studious type, graduating in just 3.5 years from a prestigious university. Her parents never spoiled her with much of anything because they come from a lower middle class background. In fact, Victoria regularly sends her parents money to help them instead. Victoria believes she’s found the one, although she’s frustrated her boyfriend has to travel so much for work. Her boyfriend is also relatively good looking with the ability to make anyone feel at ease, so she’s worried she won’t be able to hang on to him.

Amanda and Victoria are as different as can be. Amanda loves to dress in expensive clothes, drink, and party it up until 3am several days a week no problem. Victoria, on the other hand, is Target’s biggest fan and would much rather stay home and watch a good DVD while curled up on the sofa. Where Amanda enjoys being the center of attention where men buy her drinks, Victoria does not. Victoria would rather have a glass of wine and get into deeper conversation at a lounge with her friends. Both have no trouble attracting men thanks to their good looks and vibrant personalities. But both of them deep down would prefer to be done with the game of dating and find their rock.

So it was with great interest to hear how each would respond to the question:

If you were broke, deep in debt, or unemployed, would you settle for a less than ideal partner you were not physically attracted to if they promised to take care of all your money problems?” I went on to describe, “The partner is a gentleman who you get along with just fine. You won’t have gut busting conversations where you cry for joy, but you’re able to sit in silence for half an hour to enjoy the scenery and also be able to talk to him for an hour non stop about life.

THE RESPONSES YOU’VE BEEN WAITING FOR (PARAPHRASED)

Younger Amanda:

“If he’s willing to be my friend and take care of me, why not? I’m emotionally spent and not tied down to anybody right now. There’s nothing wrong with having a suga lova! There’s no way I can pay off all my credit card bills without some help. I also need to decide on a job quick and stop spending so much money. I don’t know what the future holds, but if a rich guy wants to come in my life and pay all my bills in exchange for some companionship, why not. We’re both adults here. I’ll still date other guys.”

This was the point where Amanda showed me some of the pictures of guys she’s been romantically involved with after her break up. I was surprised because none of them came close to matching her looks. But when I learned about their backgrounds, I understood completely. One guy is a Hollywood TV producer. Another guy is in tech sales and earns a six figure income. One comes from a super wealthy family with a trust fund. And another fella works at a big law firm.

Then there is this one guy I couldn’t quite figure out. He’s an average looking 40+ year old bartender who doesn’t seem to be wealthy, isn’t particularly stable, stalky, not particularly attractive, and constantly meets girls all the time due to the nature of his profession. But for some reason, Amanda is infatuated with him. The bartender is one of several guys she’s dating mind you. But by listening to the way Amanda talks about the bartender, I could tell he was number one. Love works in strange ways and more power to them.

Older Victoria:

“Are you freaking kidding me? There is no way I’m going to be intimate with some nasty guy just so he can solve all my money problems, which I wouldn’t have in the first place because I wouldn’t be so irresponsible!

“Oh come on, it can’t be that bad! He might have a super hairy back and permanently sweaty gut folds, but what’s the big deal?” I egged Victoria on.

BARF! I would rather move back in with my mom and live alone than be with someone less than ideal!” Victoria retorted.

“Really? There’s nothing worse than being alone and miserable during a time when you’re supposed to be full of love. Imagine him asking you to stay in his San Francisco penthouse for free while he hooked you up with a nice job thanks to all his connections?” I responded.

“No. No. NO! I would rather work in a diner for $8 an hour than depend on someone to live. Depending on someone for money is worse than being alone. I believe every woman can make it on her own. No woman should depend on a man for anything. No woman should ever settle! Besides, hello. I’ve got someone already.”

Fair enough. Victoria made her stance crystal clear and any more prodding would result in a slap in the face most likely. I just wonder if Victoria would take a softer stance if she was single.

TURNING THE QUESTION AROUND

It’s only fair that I answer my own question. So I told the ladies,

If I was broke, in debt, or long-term unemployed, I’d absolutely take up a kind woman’s offer to help me out in exchange for being with her, especially if I’m alone. I fear what will happen if loneliness is combined with financial drudgery. I wouldn’t care how unattractive she was to an extent. My heart would be so grateful that someone was willing to extend a hand during my darkest time. To feel wanted is all of us ever really need. She would be an angel.

Amanda appreciated my response, largely because she feels the same way. Victoria came around a little bit, but still stood her ground about not settling for another man. Victoria is lucky because she already has someone in her life for so long. Whereas with Amanda, although she has many suitors, none of them can fully fill her heart the same way her ex-boyfriend did for now.

Amanda is sort of stuck in limbo where she doesn’t feel much of anything for anybody, except for her bartender friend. She’s waiting for her heart to heal so someone can sweep her off her feet.

The other derivative question to think about is which woman would you choose to date or be in a long term, committed relationship. This will be a topic of a future post.

TAKEAWAYS FROM THE CONVERSATION

I know this post might seem a little far-fetched for some, but I think it’s important to talk about relationship issues because we’ll all experience some type of relationship turbulence at some point in our lives. Life is infinitely better when there’s someone to share experiences with. Being adept at relationships also drastically helps you in your career prospects.

Five takeaways from this conversation.

1) It’s hard to put ourselves in a different situation and come up with a rational answer. Victoria receives lots of love from her boyfriend and can’t fathom settling for someone less to help fix her money problems because she’s not single and she’s not broke. Amanda is broke and is happy to have as many suitors woo her as possible while she’s still going through heartbreak. Nobody can deny feeling good when someone wants to take care of you therefore she doesn’t see the problem with being with multiple men at one time. A good exercise is for all of us to reflect on a time when things were less than ideal in order to increase our understanding of the other side. It’s easy to forget our past struggles if we’ve been living a good life for an extended period of time.

2) It’s easier to engage in destructive behavior after a breakup. We hang on to anything and anyone who makes us feel special. 10 men are better than one man to fill Amanda’s void. It’s as if she’s trying to show what her ex is missing to potentially deleterious consequences. It’s probably best to slow down and stop dating altogether until she decide exactly what she wants. But only a professional or herself can make that decision. When we already have someone special, we feel dangerously invincible. We look at other people’s sad relationship situations and think it couldn’t happen to us. Bad things happen all the time and I don’t think we should take our relationships for granted even though it’s easy to do. We must actively work towards keep our relationships as fresh as the first year we met.

3) The lack of money gets in the way of relationships all the time. Amanda’s ex-boyfriend was always working late until the night, leaving little together time. Amanda was always working as well which compounded problems that led to outside relationships with co-workers by both sides. If they had money, neither would have to work so hard, or have to work at all. They wouldn’t have to fight about money, get into credit card debt, or worry about their future as much. Money provides so many more options for those with money and those who are looking to be someone with money. Sure there are plenty of people with money with enormous problems. But the lack of money and choices are not two of them.

4) Money makes dating much easier. If the men in Amanda’s life didn’t have so much money, there’s little chance in hell they’d be able to be with women who look like Amanda. Manhattan has shown me multiple times how having money makes you much more attractive to someone due to access, convenience, and the fact that everything is so expensive in Manhattan. Although the bartender Amanda is dating isn’t rich, he’s got the power to let anybody into his establishment where there are regularly lines around the block. For someone who loves to party, being able to walk right up to the bouncer to get in and drink for free is attractive. I don’t know many women who would say ‘no’ to a fully paid for week in the South of France do you?

5) “Another time, another place.” So much about having a good relationship is timing. The last thing I wanted was to be locked down in my 20s because of my strong desire to reach a certain level in my career. Only after age 30 did I change my mindset to wanting to settle down. Amanda admitted she’s in a weird place right now with lots going on. I could tell, and I’m sure every guy dating her can tell as well. As a result, no guy is going to be fully committed to wooing Amanda to make her their girl until Amanda gets her mind straight. If a guy is just going to be one of many, then he’ll have his fun and keep on looking. If Victoria was single when we had our conversation, she’d be exactly what every man is looking for: stable, independent and beautiful. Let’s hope her boyfriend recognizes how lucky he is before she’s gone.

Relationships are complicated. When money is involved, relationships can become harder to solve than a jumbled 5X5 Rubik’s cube. Despite the complexity, I don’t think we should stop trying to understand.

Readers, what would you do if you were broke, in debt, and unemployed and someone offered to take care of you in exchange for your companionship? How much does age and maturity have to do with the differences in both women’s attitudes? Have you ever come across an Amanda or a Victoria before? If so, how was your experience? 

Regards,

Sam

 

Sam started Financial Samurai in 2009 during the depths of the financial crisis as a way to make sense of chaos. After 13 years working on Wall Street, Sam decided to retire in 2012 to utilize everything he learned in business school to focus on online entrepreneurship.

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Comments

  1. says

    This is a fascinating post, Sam. From what I’ve heard/observed, one of the most basic needs of a woman is their security. If a man makes them feel insecure in some way then it’s a problem. I think they way you lay out the conversations above supports that– Amanda is insecure about her finances whereas Victoria is not, so she doesn’t have to “settle”.

    • says

      Yes, financial security does bring about more choices, including the choice to just wait things out.

      I realize now I wasn’t being too fair in describing Amanda’s situation. She is focused on finding a job and im sure she will get one bc she knows a lot of people and is good at what she does. The fact of the matter is that Victoria also has 6-7 years of work experience so it’s a tough financial comparison.

  2. says

    haha, maybe it’s a miami thing. When I lived there I had a couple of friends that let themselves become “companions” for a very generous older gentleman. He would fly them around occasionally to do things like fly them out to watch the superbowl in person or be his arm candy at various events in town. Because there was no sex they both claimed it was on the up and up and everyone knew what they were getting out of the unspoken agreement. But it still felt pretty skeezy to me and when I got invited along I declined. I don’t like any relationships where I feel like I owe the other person anything.

  3. says

    Hmmmmm…..

    In my last relationship (ten years ago!) before marrying my husband, I stayed way too long for financial reasons. He wasn’t my sugar daddy or anything but I didn’t want to move out on my own. I finally ended up leaving him and moving in with my parents for a short time before I could properly take care of myself.

  4. says

    Great post… I’ve certainly come across Victoria and Amandas.

    For me personally, I think the decision is made with a little bit Victoria and a little bit Amanda. I think love includes many factors… and one of them is financial. Not necessarily that he has tons of cash, but that he is on the same page financially. If the guy refused to care about our/his/my financial situation, I wouldn’t find that attractive to begin with. If he had tons of money and just wanted to “take care of me”, that would be scary too. I don’t want to be taken care of. I want us to work together to get ourselves financially where WE want to be.

  5. says

    I could never be with someone just for monetary reasons, and I know that from experience. My dad was a great person when he was alive, but my mother used him for money and it tore them both apart.

  6. Insourcelife says

    “If a rich guy wants to come in my life and pay all my bills in exchange for some companionship, why not” – This sounds like a step away from the oldest profession.

    How about working on this first before selling your “companionship”? Amanda’s words “I also need to decide on a job quick and stop spending so much money”.

    • says

      A relationship is all about give and take. Amanda is a mature woman who is single and free to date whom she pleases. She is focused on finding a job to stay in Miami and is not looking for something serious at the moment.

  7. Chris says

    Sam, I really enjoy your well researched and thought out articles, but, every time you write about relationships, I sigh. My .02, stop looking for the shiny package with a bow on top, lasting love doesn’t work that way. You’re an intellectual and I suspect if you don’t end up with someone who is at least close, to your mental equal, you’ll soon get bored and start to stray. Lasting love in a relationship is way more about friendship and mutual interests, the sex fades fast, though still important, the true glue will be your friendship connection and how much you enjoy sharing your time with said person. Stop making relationships so much about money, you’re on the wrong track.

  8. Dz says

    Money not buy U love – guaranteed, are U trying to do this? Or measure love to money? Stupid thing. If money is concerned than it is not love. If you want to buy relationship – go get do it, alternatively U can buy some sex it is easier. There was one good measure for love – will other person voluntary choose to die for U? Or stay with U when U go broke? And disabled? I don’t think U can buy this for money.

    On the other side, life with more money is easier when with less money. Thus nice man with money is better than just nice man.

    And some killing questions to U – Do U want to be measured by money? Do U want to have relations with someone if U know that it is about money, not U personally? Or even have a suspicion about it? Both ways are ok, but that is 2 different major choices in life.

    There was somewhere in internet interesting correspondence about this:

    First, it was a young lady make open letter saying that she is tired of relationship with poor guys and wants to stick to a wealthy men and kinda wanna sell her beauty and devotion to him.

    Than some time after was exact clear answer from some stock guy (some points I remember):
    1. If U are trying to exchange U for money its is investment for me and thus need to be measured.
    2. I have good NW now (my money) and with every year it will be bigger (because I am smart in finance) thus it will appreciate
    3. Your NW (young body) already has negative cash-flow now (cosmetics, clothes etc.) which with every year become only more negative (you’ll need to maintain your beauty)
    4. Your NW will also heavily depreciate because woman in 20 has less value than woman in 30 and than in 40.

    Than PURE financial reasoning: why to exchange increasing asset for heavily appreciated?- what a stupid financial move.

    Never try to mix money and love – it is not worth, and not really possible.

    P.S. One other stupid pattern I see in this post – why are U sticking (or even thinking) of girl with problems (financial, family, whatever). There plenty without problems. If U solve her problems there will be no long term gratitude to U – guaranteed (just practical observations). Don’t waste your time – just stay away.

  9. nbsdmp says

    From time to time I worry about this one. Honestly the vast majority of people out there struggle with money issues and it is rare that I’ve come across an individual that really has their act together. I will admit that I think because I am FI, relatively affluent, and not completely ugly, women do gravitate towards these attributes. I have dated an Amanda on more than one occasion who think I will save them from their irresponsible past and their debt…that all of the sudden they deserve a certain lifestyle. These days the Amanda’s of the world are a little easier to sniff out early and kick to the curb, but sometimes the good one’s are so scared of making a mistake they never really put themselves out there out of fear of being hurt or taken advantage of. Dating can be a ton of fun & it can also be very cruel, but Sam I’d say the Amanda’s outnumber the Victoria’s by 5/1.

    • says

      I have just never met an Amanda before. A tamer Amanda yes, but not this one.

      You are probably right about the ratio of 5:1. A friend of mine at dinner said the same thing and told me various examples.

      I need to branch out more.

      • nbsdmp says

        The problem with the Amanda’s of the world is they are usually more fun than the non-risk taker Victoria. I have a lovely woman who I dated briefly but am still friends with that fits Vic’s profile perfectly, attractive, a Cardiologist making $500k +, but damn…just not as much fun to be with. Amanda is willing to drop everything on a Thursday at 3pm and head out of town on whim to go do something fun…Victoria needs a “plan” and a couple of days to pack the right 74 outfits she might need for the 3 days. You need a little bit of both to have a good combo.

  10. Geek says

    Money is just one more thing that makes a potential partner attractive or not. I’m sure we’d all love to think that our partners are with us for our hot bodies and above average charm.
    No amount of money would make up for sweaty gut folds but as one element of a persons attractiveness, it would probably compensate for a couple of shortfalls.
    ask Hugh Hefner.

  11. says

    I am a very practical person, but at this point in time I cannot see myself being with someone just for monetary reason and companionship. However, I cannot fully say I’ll given the same answer if I am in the same predicament as Amanda.

  12. says

    That’s interesting. I suspect being single and broke would influence my decision on this. I’m with Vicky right now because I’m in a similar situation. I’m comfortable financially and have a loving spouse and kid. It’s easy to be picky when you’re in a good position. When you have less choices, sometime good enough is good enough.

    • says

      Ahh, but Amanda actually has tons and tons of choices because she’s good looking. There’s no end to the number of suitors she has. I think I’m biased because none of the guys she showed me I thought were very attractive at all so ok trying to understand why she is with them.

  13. says

    I can’t really put myself in those shoes because I’ve always been good with money so I could never see myself broke, plus I’m a guy and can’t imagine a suga momma coming to my rescue if I were broke. Take away the money issues, I think Amanda’s response is more indicative of a woman in her 30s (once again, taking away the money part). “A who you get along with just fine. You won’t have gut busting conversations where you cry for joy, but you’re able to sit in silence for half an hour to enjoy the scenery and also be able to talk to him for an hour non stop about life.” I’ve known many women in their 20s look for that ideal man and were very picky. In their 30s…not that they are “settling” but thier priorities change and they are more realistic. They want someone who is a provider, they want security, someone who is a friend that they can talk to…sure they want to be attracted to him, but he doesn’t have to be gorgeous. Beauty is in the eye of the beholder.

  14. says

    I’m with Victoria. I favor independence and not owing anyone anything. I’m also somewhat of a workaholic so that is probably part of it. I feel happy making money from my own hard work and will not accumulate credit card debt that I can’t pay off in cash. I saw my parents raise me having to constantly seek financial assistance from their parents so I wanted no part of that. Love and life are complicated. But becoming financially responsible and independent are part of growing up. Couples need to be on the same page about monetary goals and values for things to work but there are lots of other things that have to click too.

    • says

      I’m just saying it’s hard for those who are older or in a good financial place to truly understand those who aren’t are going through. I understand why Amanda does what she does now, but only after I gave it a lot of thought and hours writing this post.

  15. B says

    Fun post. I would not want to date someone who makes less money or has a lower net worth, even though I’m personally in a great position financially and hardly need anyone. I can’t say exactly what it is, but a relationship simply wouldn’t work if I was the more successful one. Maybe it’s tradition. The way I was raised. Definitely looks hold little power over me now, especially cmopared to when I was a teenager or early 20s, other than that because I’m a fit and active person, I would expect that in a partner. Otherwise, shared values are # 1, and one value I hold dear is financial security. As soon as I sensed that he wouldn’t add to that, then it’d be over. It’s totally a gut reaction. We all have ‘things’ that turn us on and off, I guess.

  16. whoanelly says

    No I wouldn’t. I’d rather be broke than miserable. There are plenty of fish in the sea to avoid settling. There’s no such thing as an ideal partner anyway. Only a partner who is ideally suited for you. My husband and I are not FI (yet), but we’re the richest people in the world. I’ve known many girls like Amanda and I hate to put it this way but later in life they winded up becoming chewed-up, bitter people.

    • whoanelly says

      Fortunately for me if I was single and broke, I’d probably move in with a relative or friend temporarily until I could find my feet. I’d have to be way more desperate than Amanda to settle.

  17. Jennifer says

    We all settle in some way or form, so it’s logical for Amanda to be with someone who could help her out, especially if he’s kind as you put it.

    You are right about people in relationships who say they would never. They don’t have the qualifications to opine or judge someone who is by themselves.

    Amanda will eventually find someone. Let’s just hope she stays safe.

  18. says

    Interesting topic. I wonder just how differently people think about this, based on gender. Maybe not much, but then again who knows.

    As for me, I couldn’t imagine living with the feeling of “owing” a woman for financially taking care of me if I was in dire straits. It’s like unspoken debt. Also wouldn’t like to be used, and pigeonholed into some 1950′s role as the expected “sole provider” just because I’m male.

    The best thing is a shared journey where two people are on the same page and both contributing to the relationship in a way that genuinely works for both of them. Regardless of how much each person has. At least that’s my view, though there’s no right answer of course.

  19. Linda says

    I’m with Victoria if I’m by myself. If I had dependent children and the nice, wealthy, not-hot man was willing to step in, I might just make him believe that I think I’m the luckiest woman alive to have such a man. The deal is that he’d never know, because every man wants to be someone’s Knight in Shining Armor. And who knows? I might be so happy that my kids are safe, the nice man might start looking very attractive to me. Not such a bad bargain.

  20. Jason says

    I have to agree with another post above; these relationship articles that throw in financial motivation are just uncomfortable to read. We all know that there are people that date just because of someone’s large checkbook, but it’s just sad to read about it.

    But to answer the question: If I were broke, I don’t think I’d date anyone at all until I dug myself out, regardless of any “promises” any potential mates made to me.

  21. says

    Women want security. Men want some damn sex!

    I had a friend from high school get married recently. This dude got into massive debt in his teens. I’m talking 40k on credit. So what did he do? He found a sugar mama! He married some lady in her 30s who he met online. Oh and she’s rich, but, um, sort of out of shape.

    If I was broke, I would hustle and meet women through my hustle.

  22. says

    I get it! Some peole have nifty pick up lines, you do survey questions. Apparently it works! Which one would you actually date?

    On a semiserious note, I would take genuine help from anyone who wants to give it. If it is just using people, count me out. Dating usually congers up a more emotional response which changes the dynamic. I could not take advantage of someone just because I had hard times. I would be completely honest whcich would probably limit my dating.

  23. says

    I definitely wouldn’t marry someone for financial security, and, I wouldn’t marry someone in financial trouble. Finding our way around the labyrinth of life is a task I think every adult should have to pursue. Relying on the money of another person is a passive and sad way to live. And, there’s absolutely no guarantee that the millionaire you marry will still have money next year, or even next week. William C. Durant, one of the founders of General Motors, lost all his money during the Great Depression and ended up running a bowling alley in Flint, Michigan.

      • says

        I’m not broke now, but was in bad trouble about 11 years ago ($26 of credit card debt, $28 student loans, no assets). I live in Seattle, and was working at Microsoft, and had a fair share of well-off men pursuing me. I wanted to be successful my own, and with a bunch of hard work I am now out of debt and own investments and part of a home (the other part is owned by my bank, as I still have a mortgage).

  24. K says

    Two things about this article really caught my eye: (1) “If Victoria was single when we had our conversation, she’d be exactly what every man is looking for: stable, independent and beautiful” and (2) “The other derivative question to think about is which woman would you choose to date or be in a long term, committed relationship.” I think the answer to the latter question from a lot of men might surprise you. I am 29, single, a very beautiful woman with a body I take very good care of, a lawyer in a large law firm who practices corporate and international law, very independent, very successful, make six figures and the first number isn’t a 1, own rental property, am generous, am terribly knowledgeable about tax and investment strategies, am building passive income, love to travel for extended time periods—alone even—and have done so in multiple continents, speak multiple languages, have a close family with parents still together, am fascinated by entreprenuership, play piano, play violin, sail, rock climb, scuba, am intellectual, adventurous and am extremely loving and loyal in a relationship.

    I have been single since I started practicing law (four years ago) and cannot find one remotely intellectual and successful guy interested in pursuing a relationship with me (dating, fine…but not a relationship.) (While I have no need for a guy to take care of me or be successful monetarily, I do need to have intellectual conversation and be with someone that shares my values—-saving, investing, passive income, diversification, travel, personal growth, etc.) However, there are plenty of not so successful and not so intellectual guys who beg me to date them and ask if I’d be willing to let them be house-husbands. Really. I am actually asked that on multiple occasions. The point is that I’d be very surprised if any successful guy would actully choose Victoria over Amanda.

    • says

      Do you live in SF? If so, we should meet up and trade notes.

      Four years is a long time! I’m sorry you haven’t found a more
      meaningful guy to be with. As soon as you do, it’s going to be a different world.

      Amandas are very attractive for men because they love the challenge,
      adventure, and spice that her type brings. Guys also love to be the caretakers.

      • K says

        Orange County, actually. (I suppose it’s possible that’s part of the problem.). I’m in SF for work relatively often though and would be happy to meet up to trade notes. I do have some rather good stories along these lines . . . Perhaps fodder for a new post.

        • says

          Can’t have enough fodder for new posts! All these posts are the result of experiences from speaking with interesting folks. Definitely ping me next time you are in SF. My endless summer is over and I should be here more often. Cheers

  25. says

    I was unemployed when I proposed to my current wife. She got to tease me about being my “sugar momma” for a bit while I looked for my next gig, but I’m financially savvy enough to have substantial savings so there was never any significant worry on either of our parts.

    As long as you have the money talk before you get seriously involved, so you know you’re on the same page, whatever that page might be, you should be ok.

    You get hurt when you make assumptions – having the talk brings those assumptions to the surface so you can deal with them.

    Trust me, the men “Amanda” is supposedly playing know exactly what the deal is. As does the bartender, just from the other direction, since he’s able to recognize her for who she is, and deal with her appropriately (hence the infatuation). Human behavior is weirdly fascinating.

    • says

      Yes, open honesty about finances is so important.

      If Amanda and her suitors are open to have fun, then more fun to them. The key is to try and not get too attached after several encounters. That’s when things can get difficult.

  26. Shaun says

    I think how you answer this question depends on how long you’ve been broke. I’ve done fine thus would say no way cause I have a hard time envisioning myself poor with no other way out. Take away all my money or put a huge debt on my head and I still have valuable skills and over time would work out of it.

    I also enjoy that both the women do the opposite of what they said. The one girl who said no is dating a wealthy guy and the girl who said yes is in love with the bartender.

    Also don’t be surprised the girl likes the pudgy bartender. Girls are also attracted to social status as much or more than looks and there is no profession on earth with as much feigned social status as bartender. Everybody in the room is sucking up to you for free drinks, they all are trying to get your attention, you know and are friendly with most people. It is like being a mini-celebrity.

    • says

      I think you are spot on about the bartender, especially one who is a bar manager at a hot spot in NYC. Doors are a damn pain if you don’t know someone.
      So for someone who loves to go out, this relationship makes absolute sense. For a more homebody like Victoria, she wouldn’t give a damn and want to go out with someone more sophisticated.

      Again, no right or wrong preference. Just fascinating to understand each side’s desires.

  27. says

    I would rather rent out the sunny main floor of my home and move myself down to the chilly, dark basement than be with someone for money.

    I understand that George Clooney is single again, poor man, and if he wanted me to live with him and pay all my bills so hat he was not so lonely I would make an exception. I do feel sorry for him when he is wandering around that big mansion in Italy all by himself.

    Could you do a yearly financial update on younger Amanda? She likes to spend and if she doesn’t find a husband with money to burn she could struggle in the future.

    • says

      Nice of you to sacrifice being with George!

      I think Amanda will be fine. I’m sure she’ll find someone stable with means, and if not her parents can take care of her. She’s a fun spirit who will easily attract people to want to help her.

  28. says

    Please don’t tell me you become one of Amanda’s boy toys, Sam!

    Maybe I’m misinterpreting, but I don’t think what Amanda is doing is “settling for a less than ideal partner.” Instead, she’s playing the field and taking advantage…she’s become a “user” so to say. I’m sure it happens all the time, but I don’t agree with that approach to life. As a guy, I wouldn’t go anywhere near her.

    As for Victoria, if she actually were in a deplorable situation, I’m sure she’d soften her stance somewhat (although hopefully to nowhere near the levels of Amanda).

    I think I’d be willing to compromise to “save” myself, but there’d have to be at least some admirable qualities in that person.

    • says

      Boy toy…. haven’t heard that in a while! No, not to worry.

      I’m afraid I’ve painted Amanda in too negative a light in this post and she’s being set up to fail. She’s on the mend now, is not in a good financial place, and is just dating around. Many guys use wealth to display they are worthy, so what is so bad if a woman accepts? Amanda is not golddigging. Her favorite is the bartender after all. I was the fella presenting such a situation to her and not the other way around.

      I appreciate Amanda for her candor because I think most wouldn’t admit to saying “yes, why not” even though that’s exactly what most people would do when nobody is looking.

      • says

        I did make the disclaimer “Maybe I’m misinterpreting.” I guess I’ve just known or known of too many women who’ve played the field like what it seemed like Amanda was doing. I understand she’s in a tough spot and “on the mend”, but accepting the affection of multiple men just seems….I don’t know. I mean, I thought the premise of your post is would you settle for a less than ideal partner, NOT partnerS.

        It’s ok to admit you’re one of her new flings, Sam… ranked right behind the bartender. We won’t hold it against you!!!

  29. says

    Kudos to Victoria for standing her ground on her position; women can take care of themselves without a man. :) Amanda, on the other hand, has really bought into the whole Cinderella-fairy tale and is waiting for Prince Charming to sweep her off her feet. Seriously, someone needs to write women-empowered fairy tales to replace those centuries old stories! It’s undermining women’s self-confidence!

  30. says

    I’ve never been drop dead gorgeous, but in my twenties I was cute and thin, and almost always single. I had times of being broke and feeling completely unstable. I’ve always been more for personality than looks in a guy. There were several times that a wealthier guy tried to date me, and I always ran from that. The minute a guy started trying to take care of me, or when I started to feel like “arm candy”, I was gone. Even now in my current relationship, I have a hard time whenever it starts to feel like my boyfriend is trying to take care of me.

    My younger sister however takes full advantage of her looks and what she can get with them. She’s even gone as far as to subscribe to a “Sugar Daddy” website, that matches pretty young women with wealthy (mainly older) men. She casually dated several guys she met through the site, and had no problem with them giving her money for clothes, to get her hair/nails done, or paying her bills. She traveled with them, went to plays and other events, ate at many nice restaurants.

    I think it has less to do with being single and broke, and more to do with what you want in a relationship, and how you see yourself in relation to a partner. I find security in someone treating me as an equal, a partner, and feeling like I have control over my own life. Others feel security in being taken care of, in not having to worry about anything, or in having nice things and expensive experiences.

    • says

      Good perspective. I imagine there’s a little bit of both feelings in everyone.

      I just don’t believe it when most people say they wouldn’t settle if they’ve been broke for a log period of time. That would be irrational, especially if the man is kind and they get a long.

  31. BSS says

    Death is not something scary for, me even something that I look forward to. Because that way my misery will end. when my beloved goes away my soul die slowly, nothing beats love pain …..

  32. says

    I suspect that the bartender has other girls, besides Amanda. So he acts cool towards her. While the well-to-do guys fawn over and bend over backwards for her.

    Frankly, I don’t know why a successful guy would choose either girl. Choose BOTH of them … at the same time. Like what the bartender is doing and like what Amanda is doing.

  33. says

    Oh I love this post – and I see it all the time as a financial planner. I can think of at least 3 of my clients and 2 of my friends whose financial situation got a whole lot better after they got married. Love or money? That’s the eternal question.

  34. says

    It is really sad that some people have to prostitute themselves or stay with abusive partners in order to keep some measure of financial security. For a lot of people this isn’t a hypothetical question and that really sucks.

    My price isn’t broke, in debt, etc. because I still have a family safety net, friends, and skills and an education to fall back on. But if I didn’t have those and my kids were starving, who knows what I would do. Social safety nets are important.

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