The Pros and Cons of Online Dating: What If She’s A Man, Baby?

Santorini Donkey

If you want to date, then you might as well participate in online dating. With Tinder, Bumble, and a bunch of other apps, online dating is the most efficient way to have fun and find someone.

My buddy, Craig has disappeared.  We used to keep in touch a couple times a week and play some tennis, but not anymore.  After a match at the club yesterday, I saw him walk by with some girl to the hot tub.  Interesting, I thought to myself.  So he's got a new flame!

After my match, I curiously hopped on back like any good nosy friend would to see what was up.  Unfortunately, she was already gone.  Drats!  But there he was, with a big smile on his face, sipping some sangria he brought from home.  “Wassssssup?” I asked Craig.

“Yo, Sam!  Good seeing you man.  Not much.  I was just on a 3 hour date with a girl I met online!  We chilled in the back, watched the Blue Angels, and enjoyed the bubbles.”, Craig explained.

“Oh really?  Tell me more about this online dating stuff!” I inquired curiously.

Craig proceeded to tell me how he had recently signed up for this free online dating site called OKCupid, and how he was getting all these dates.  “Two a week, at least!”, he mentioned.  “There are so many women online, it's ridiculous!  I feel like a rockstar!”

After an hour of conversation and some further research on my own (6 months undercover), I've come up with Sam's guide to understanding online dating.


* You know what they want. It's rough for guys to pick up girls at a bar sometimes.  Even if the girl is with her girlfriends or by herself, the law of logic states that if you find her attractive, every other guy will find her attractive, which means she already has a boyfriend and you are wasting your time!  At least if she fills out a profile online, it is certain she's looking for love, unless stated otherwise.

* Try before you buy. You can “wink”, flirt and send messages to an interested candidate all you want.  If she or he doesn't respond, no big deal because you haven't spent much effort or any money.  For broke ass guys all around, online dating site is a gift from the heavens.  No longer can you question why the rich, ugly guys get all the women either!

* Way more efficient. Any good playboy or playgirl knows that finding someone is a numbers game.  1 out of 10 will show interest for the average male.  But, what a pain in the ass to talk to 10 different women live!  Instead, you can go online and ping literally a hundred at once (copy and paste your generic sassy message even) and bam!  Much better yield.

* You can search for what you want.  If you like 6′ 6″ inch beefcakes who look Ron Gronkowski of the New England Patriots, you can search for him!  If you like women with unadulterated, butternut skin who look like Jessica Alba………. keep dreaming sucker!  They are already taken!


* What if she's a man, baby. What looks like a woman, could be a man, and vice versa!  You can't really know for sure what someone looks like until you see them in person.  They could have glamor shots done to make them look skinnier, prettier, or more buff!  How many times do you say “HUH? WTF!” in your mind after seeing someone in real life after you see their photograph?  Deception is so easy!

* Other people might see. You're putting yourself out there for the whole world to potentially see.  For those who love privacy, this is a tough hurdle to overcome.  Yet, if you try and put up a less than honest picture or bio, you will get less than effective responses from the online community.  That said, you might look so hot that you will be inundated with every horny guy or girl on the planet, which is kind of what you want since then you can choose the best.

* Unwanted attention.  You never know who you're going to meet online.  Women should probably be more careful than men, because when was the last time you heard of a woman stalker?  If you are a particularly attractive woman, you may get a disproportionate amount of interest online which you cannot handle.  If you don't respond to some, maybe you'll offend them.  Then the stalker might come out!

Related: Career Or Love?


Successful online dating requires a fantastic profile. Here are some tips.

* Be honest. Everything from a recent picture, to your biography should be honest.  If you start off on an honest track, you know that whoever pings you or accepts your interest is truly interested in who you are.  People get discouraged online as well and therefore start fudging how great they are: age, income, occupation, etc.  The truth comes out in the end, so you might as well be truthful in the beginning.

* Be responsive. If someone pings you, ping them back because you never know if he or she could be a match!  Unless you are super hot and getting an uncontrollable amount of messages, in which case you don't need to be online anyway, get back to people who make the effort to want to get to know you.  Even a “Thanks, but I don't think we'll match” is good enough.  If you don't want to respond after that, no problem.

* Show your personality. You don't want to have another typical profile which says that your favorite movie is The Notebook and you like hiking and long walks on the beach.  Try to differentiate yourself with something memorable like “Love skydiving, but am still afraid of heights,” or “Sipping chardonnays and gorging on foot high pastrami sandwich overlooking the Golden Gate Bridge.”  You know, something a little more descriptive and original.

* Don't just go after the hot ones. You can run with the herd, or you can find your own path.  The hottest candidates are the ones who get bombarded by everyone.  Too much demand!  It's the same concept with buying property.  Yes, that choice location property is more expensive than others, but it will always command outsized demand and outsized prices forever.  If you can look a little down the quality curve, you will find much more opportunity!

Related: How To Become Happier

Online Dating Is Here To Stay

Online dating has become mainstream.  In fact, I'm surprised not more people go the online dating route.  It's efficient, accepted, and free often times.  Just beware of women with large Adam's apples and men with crazy eyes!

As Saito said, “Don't you want to take a leap of faith? Or become an old man, filled with regret, waiting to die alone?”

Related posts:

The New Rule For Engagement Ring Buying

A Wedding Rule To Follow So You Don't End Up Broke And Alone

Photo: Donkey Love, Santorini, 2011.  SD.

About The Author

39 thoughts on “The Pros and Cons of Online Dating: What If She’s A Man, Baby?”

  1. Pingback: Should The Man Pick Up The Tab On a Date? | Financial Samurai

  2. Online dating is indeed getting a widespread recognition. People just love the idea of meeting somebody from behind somebody else’s computer. But be warned, fraud and scams lurk in all dating sites. Who knows you could be spending time with a cyber-criminal and you are his next prey.

  3. I have a few friends that are currently trying online dating, but haven’t had much success. I don’t know anyone personally who has met their significant other through online dating, but its definitely something that is the norm now. I met my significant other through a mutual friend. Call me old-fashioned but I like meeting people through friends, at least you know they’re decent people right off the bat, because they are friends with your friends. However, I do understand that because people are busy with work and other commitments it is hard to meet people and online dating would be a good choice.

  4. “I guess it would be easier than trying to meet girls in a bar. I never had much luck with that”

    If you’re outside the mainstream and the likelihood of finding somebody even remotely tolerable in a bar is close to nil, then online is a fabulous alternative. I have personally found online dating to be a much more effective way to find people that can engage intellectually (with the low-enough cost of filtering out the rubbish). While I have tried both in-person and online, I have had much more success online by getting to know someone a *bit* more before even stepping out my door. My last two long-term relationships have started on OkC, and the current one is 9 months old. I must say they are much less drama than the ones started in person.

  5. I think it’s how many people are finding “love” these days. Most people I know are now finding love in our church, because it’s pretty big and full of young people. I think that’s pretty awesome, too, because they get to know someone in person before all the flirting messages and stuff. They also get to see them in real life and lock eyes with them instead of sending message to an online headshot.

  6. Oh, my gosh. I saw this show once where there were three guys competing for the same girl. At the end she chose the guy she wanted a relationships with, and then it turned out that SHE was a HE. And the guy s/he chose decided he still wanted to pursue a relationship with her!

    I turned off the TV and got a life. It was a turning point.

    But I do know a lot of people who have met online. It’s worked for a lot of them. And hasn’t at all for others. But it definitely doesn’t carry the same stigma it did a decade ago.

  7. My cousin and her fiance met online; they have each visited one another in their respective countries. Now, they just need to figure out how to live in the same country, which isn’t easy with all of the government red tape.

  8. Online dating? It’s for early retirees who have all the time in the world to flick through photos and bios. Me? I’d have to hire a personal assistant to do the sifting. Time is far too precious to waste on a virtual cattle market.

  9. This guy has an interesting take on it and writes how as a management consultant he basically solved it:

  10. Dating sites are big business!! I have a friend who is paying the Millionaire Matchmaker’s assistant $3k/hour to find her a mate (she’s very successful). I was like, REALLY?! Just pay me that money and I will find you someone! Except I have no previous matchmaking experience unless I count myself :)

  11. I am a fan of it if you do it right. The paid sites that have a huge application process that really helps identify who you are so it can find you the best match really work. I have numerous friends who have used sites like this and are all happily married. And they were people who thought they would be alone the rest of their lives and had given up.

    However free sites are a different story. If you ask me, the ones that take little effort and no payment are just people looking for booty calls.

    1. You are probably right! If you are going to pay and go through the entire application process, you are super serious. However, I think there are a lot of serious women on OKC as well. As for guys…. much less serious.

  12. Even in person its difficult to tell who’s a man and who’s a woman – especially in Thailand!

    A few year ago we were in Kanchanaburi Thailand and we were with a guide all day – we are still not sure if he/she was a man/woman!!!!

      1. It’s true. The gap between genders in Thailand is thinner than in other parts of the world. Men are effeminate and sometimes women seem somewhat boyish.

        One thing you can be pretty sure of: the woman baring a lot of skin and looking pretty lean and muscular is most likely a man, baby.


      2. Your correct I can guess and probably will be correct.

        He/she was likeky a lady boy. And like Mike said he/she had on a very short denim skirt.

        Most importantly she was a great guide and we had a wonderful day – thus – it really did/does not matter!

  13. I never had to the do online dating thing. It was just ramping up when I got married 13 years ago. I guess it would be easier than trying to meet girls in a bar. I never had much luck with that.

  14. My best friend met his wife online. It wasn’t a great fit at first, but as they got to know each other, it’s blossomed into something beautiful. I think it’s how many people are finding “love” these days. Most people I know are now finding love in our church, because it’s pretty big and full of young people. I think that’s pretty awesome, too, because they get to know someone in person before all the flirting messages and stuff. They also get to see them in real life and lock eyes with them instead of sending message to an online headshot.

  15. I met my wife on OK Cupid, and we’ve been together (dating, then engagement, then marriage) for more than two years now. It was an easy, low-stress way to get to know someone before committing to spending time time with them in a potentially awkward “first-date” scenario. I had no idea at the time what would eventually come out of the experience, but I knew that at least we’d have things in common to talk about.

    I agree with the assessments, the PROs, CONs, and TIPs are rather good.

  16. Eric J. Nisall - DollarVersity

    I’ve used online dating for years now. It’s just like dating in the real world in terms of the quality and character of the people on there. I still ended up meeting women who really didn’t know what they wanted, or wrote a bunch of stuff that ended up not being 100% accurate, or were totally different in person than how they described themselves. There were both good and bad experiences, but for someone who doesn’t have a lot of time to spend at, or any inclination to try to meet women at a bar or similar places, it’s a really viable option.

  17. i think it today’s world of cell phones and interconnectivity.. online dating really fits in nicely… myself, i am happily married– but i have seen a number of friends go through it. those that are online dating, often have a number of girls who they are texting with and sharing funny links with and such.. it makes flirting really, really easy, and allows for them to get to know each other a bit, without having to be nervous about dating someone you barely know.

  18. Hey Sam!
    I used to work for an online dating company. I strongly encourage it as another avenue in meeting others. I don’t think it works for everyone(evidently by some horror stories….or stories of the visible adams’ apples), but it does work. So why not take that chance! My current girlfriend and I met online.
    At the online company I worked for, we would receive 1-2 success stories via email sent in by our users. They’d share all the details of how they met and how happy they were. It was a good driving factor knowing that through the service provided, others were finding each other.
    Regarding Income, I find that this tends to have more meaning in densely populated areas(where cost of living is way beyond national average). It’s yet just another way of filtering out what people are comfortable with sharing.
    One main thing I’ve noticed is that online dating is like a virtual bar. Anyone can say anything about who they are. Nothing will be revealed until you meet with them for some time. The ones with more attractive photos will always get 50x winks & emails than you think. So they spend more time ignoring or skimming through emails. The best thing is to just get to know them until they are comfortable meeting up(after they have fb stalked you).


    1. Great to hear from an ex online dating company employee’s perspective!

      It must be quite an ego trip for the more attractive members of our species to be on an online dating site?

      Do you think there might be many who are just on to boost their self-esteem?

      1. Many people try online dating for various reasons. I’m sure there are a few out there that entertain their own ego. However, I try not to judge others’ reasons for their actions. If it enables them to find their significant other, that means we just made two people happy=D

    2. I’ve heard and suspected that many of the more attractive profiles are fakes, and I suspect that this might be true. Any truth to this?

      1. Eric,
        You have to realize that profiles in general are like email accounts, but just a tad more restrictive.
        I wouldn’t say the more “attractive profiles” are fake. But there are a lot of scammers trying to get money from unaware victims that are just looking to find their significant other.
        Are there fake profiles? Of course there are. Virtually the bar scene, anyone can be anyone behind a keyboard(in a sense that someone is lying to get attention). However, there is always an ongoing effort to stay 2 steps ahead of scammers and fraud, but there are always a few that slip through the cracks.

        There was also a rumor that employees create more attractive profiles to lure others. We actually enjoyed this rumor and laughed about it around the office. This is just funny and ridiculous at the same time. We don’t know who actually believed this, but in a development shop for internet sites, we just simply don’t have the time to create profiles and “lure” people into subscribing. We are constantly busy fixing bugs that users submit and enhancing the webpage for a better experience. From a business perspective, it just doesn’t make sense spending money on employees wasting time(creating fake profiles) rather than polishing a product/service that will keep a positive word of mouth socially.

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