What If She’s A Man, Baby?

Santorini Donkey

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!


* 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!


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?”

Readers, what are your thoughts and tips on online dating?  Do you know of any great success stories to share?

In the portion where it says “Income”, do you think it is poor taste for a man who earns a lot to highlight his income range, or is better to put “I’d rather not say”?  Do women really care how much a man makes after a certain amount?

Photo: Donkey Love, Santorini, 2011.  SD.



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