Online Dating: You’re Doing it Wrong

Perhaps it’s because I met my man of nearly a decade online, or maybe it just appeals to my lazy nature, but I’ve always been a fan of internet dating. Why go out to a bar when you can sit home and order potential penises from the comfort of your couch?

Incredibly, I still have friends who balk at the idea of looking for love (or sex) via the interwebs. Perhaps it’s just short-sightedness on my part, but I don’t see any downside. I mean, I’d never had much faith in love, but shopping for dates was more fun than shopping on Zappos or Etsy. Sure, for a while I pursued it with the vigor that others invest in activities like Bikram Yoga or a methamphetamine addiction, and yeah, it cost me a couple bucks (and occasionally my dignity), but after more than 500 or so fruitless dates, I met someone really great.

(Graphic: Kat Borosky/

So since I was already proselytizing my face off about this issue to my friends, and had a veneer of legitimacy due to a dating advice column and book I’d written, I decided to start a business helping people rewrite their online personals. Why not make a little dough and do good deeds at the same time? While it ultimately turned out to be a less-than-cost-effective way to make a buck, I did learn a lot about what you shouldn’t do when you’re looking for love online.

Here are a few of the more common mistakes:

When it comes to your birthday, “truthiness” is overrated. 

Until I started online dating, I firmly believed that lying was a bad thing. But over my online dating career, I quickly realized that half of the guys who copped to being “over 40” on their profiles were actually over 50 in real life. And they had no shame about shaving a few years — or decades — off. On more than one occasion, I heard some variation of, “I don’t look a day over 40 anyway,” which just goes to show that the majority of men I met were also very comfortable lying to themselves. (More inexplicable were the guys who lied about their height.) So avoid major whoppers, but feel free to subtract a few years off your age if you’re so inclined.

Why wouldn’t you be completely shameless about looking for love online?

Who cares if your boss sees your OK Cupid profile or your cousin catches you on Tinder? Why do you think they’re on there?

Lighten up.

My friend Mabel* told me she doesn’t feel “comfortable” online dating. This is a woman who hasn’t had sex in three years. As someone who went two years sans sex during one bleak period, I can tell you that a vagina stuffed with cobwebs is far more uncomfortable than meeting a stranger for cocktails and a little grab-ass. And while we’re at it — most first dates aren’t going to pan out into anything life-changing, so don’t go nuts waxing your lady bits and buying a new outfit. Relax and see what happens. There’s always time for hair removal if there’s a second date.

Rules, schmools. 

Everyone tells you to avoid controversial topics like religion and politics on a date, which is fine if your give-a-shit-meter is in the shop. But if you have any sort of principles, it’s better to be up front about them. Like the guy who informed me before I’d even finished my first drink that he didn’t “believe” in condoms. A controversial stance in these viral times, but it was also very good information, as it saved me the calories of a second drink.

Quit looking for that unicorn. 

I’m not saying you need to lower your expectations, unless your expectations are delusional, which they often are. One client I worked with was adamant that she only date Indian men and they had to be over six feet tall. Now I’m sure there are tall men of Indian descent, but Wikipedia backed up my anecdotal hypothesis that most are significantly shorter. Like an average of seven inches shorter. Furthermore, my client was tiny — maybe 5’3” tops. She was just being greedy. I told her she had to let go of one deal breaker: Indian or over six feet. She refused to budge on either and yet somehow it was my fault she never met anyone. See why I quit this business?

“You’ll find love when you stop looking for love” is a load of crap.

I can’t even count how many times well-meaning friends offered up some version of this inspirational platitude, and every single time my eyes rolled so hard it hurt. I’m a freelance writer — I’ve never worked in an office full of hot single guys, most of my friends were shacked up, and all the men I was meeting out at bars were alcoholics and/or oblivious to my charms. So I kept trawling the internet, looking for it. And one evening, after the 549th awkward date, I found it. Was it because I was wearing my lucky shirt or because I chose to ignore several glaring grammatical errors in his profile and ask him out for a drink anyway? Who knows. I wish I could be more romantic and chalk it up to fate or kismet or some other mystical bullshit, but the fact is, it was a combination of luck and numbers. By dating like a mad woman, I met a lovely man.

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3 Responses

  1. carolita

    All true! As the Carmina Burana poem goes: quicquid Venus imperat,
    labor est suavis! (whatever Venus orders is sweet work). You have to work to find love. I’m glad you were rewarded for your efforts!

  2. TueNight’s Best from 4 Months of Awesome | Tue Night

    […] Online Dating: Why You’re Doing It Wrong. Even in our advanced age, we need a little help. […]


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