How to Approach Online Dating

Our regular readers know that we’re huge proponents of online dating. When it’s used properly, it’s a great way to meet someone who shares your interests and values, which is pretty much the opposite of meeting guys in bars (i.e., is he cute enough? am I drunk enough?).

But sometimes it’s hard to figure out how, exactly to navigate this social stratosphere that no other generation has really used. What should you put on your profile? Should you message him first? What’s too sexy for a profile picture?

In our opinion, online dating works better as a conversation starter than it does as a matchmaking service. Think of it this way: you’re probably more likely to sign up for one of these sites when you’re new to a city and desperate to meet anyone—platonic friends included.

In fact, one of our friends who’s had the most success with online dating has a huge circle of friends that she meet on dating sites. This might not seem like a huge deal, but when you consider the fact that most people who sign up for these services are looking for love and come in with the highest of hopes and then quickly learn to move on at the first sign of incompatibility, it’s pretty remarkable that she keeps in touch with, much less befriends, people she romantically rejected.

But in the real world, think about situations that produce the most successful couples. How many couples meet at dinner parties or work events where they aren’t looking for love? And how many met at speed dating?

This is why we prefer free dating sites to paid subscriptions. When you sign up for OK Cupid, you’re testing the waters, seeing what’s out there. When you drop $200 for 6 months of Match.com, you’ve made a pretty big financial commitment to get what you paid for.

Guys are more attracted to women who seem laid back, casual, fun, and not too obsessed with the idea of finding “The One.” So your OK Cupid persona should project this persona. This doesn’t mean you shouldn’t ignore messages from guys with facial piercings if your entire wardrobe is Lily Pulitzer. But it does mean your profile and messages should be more of a conversation starter than a marriage proposal.

Don’t look at your profile as the place to capture your personality so that the person on the other side of the screen can get to know the real you, deepest, darkest secrets included, and then decide whether or not you two would be compatible. In the real-world dinner party scenario, you wouldn’t tell the guy sitting next to you that could absolutely, positively never date a smoker and that you fall in love too easily. Instead, you would drop tiny tidbits of information in the hopes of drawing him in to the conversation.

Your profile should do the same thing. Your “About Me” section doesn’t have to be an autobiography. It doesn’t have to sum up your personality or list your flaws. It’s supposed to give the person looking at your profile something to message you about. And that’s why vague, abstract descriptions of your personality are actually a terrible idea, because a) they’re pretty boring to read and b) what’s he going to message you—“I procrastinate too!”?

Talk about things that are more on the unique/interesting side of things, but universal enough that someone can respond with his own experience. Things like travel, hobbies, etc. Try to be both specific and open-ended so that he can ask you about it. Something like, “I once backpacked through Guatemala and resorted to eating live fish.” Specific story that naturally leads to when/how/why you ate live fish.

Same goes for messages you send potential matches. Don’t say, “I also love The Big Lebowski—I bet we would get along really well!” Try more along the lines of, “So I’m a little new to this and not really sure how this works, but I just moved to DC and I see that you do yoga—do you have any suggestions for a good studio?”

Keep it short and sweet, like you would at a dinner party.

And treat the ensuing banter like a dinner party. Don’t provide unsolicited information. Don’t send overly long messages. Keep it light and casual. Online dating is just like meeting guys at any other place—this isn’t your only shot at love, so don’t act like you think it is.