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On Playing the Dating Game to Win [Dear DBN]


Wouldn’t it be amazing if life was a Stoplight Party and it was clear who was and wasn’t available at all times? Well, it’s not. This week, how to tackle some of the trivial difficulties in the pursuit of great love.I just opened an OkCupid account. And my lovely, very tight knit group of friends all laughed at me. Okay, this is lame but I feel embarrassed and these people (whom most I’ve known since grade school) are being harshly uncool about it.

Online dating, unfortunately, is still weirdly stigmatized because, at its core, it’s an admission of your desire to be in a committed relationship. How many times have you heard, “I’m not necessarily looking for a relationship, but if I were to meet the right person…” Right, sure. The truth is, a lot of people really want to make pancakes and have Arrested Development marathons with a person they both love and want to make passionate love to. It’s just that none of us will admit it for fear of the super icky crazy terrible chance that we might appear desperate. Newsflash: If Hollywood, history and general human tendencies are any indication, everyone wants to be in love and some of those people have an Internet connection.

Online dating is no different than throwing on your cutest outfit and rouge for the bar. You are putting yourself out there in a social setting conducive to meeting people. It might be worth reminding your friends you have feelings — some that they’re hurting and some that might just get fulfilled on OkCupid.

Any tips on how a girl can hit on a complete stranger? Not really someone you happen to see on a regular basis, but if you see a guy you’ve never seen before who catches your attention.

Act lost, compliment his sweater, comment on the team he’s wearing, throw a snowball, ask him if he goes to your gym because oh man he looks so familiar and buff!

It’s not your opener or the line holding you back, it’s just the approach. Guys rarely get hit on (not including bartenders), so you could just smile and say hello and it will baffle and befuddle them. The biggest issue here is obviously The Close. But that’s easy: Carry paper and a pen so you can write down your number just before your exit.

Think about all the times you’ve been hit on and what worked versus what didn’t. Guys, shockingly, are just people. They’re usually pretty friendly, and if they’re not, their girlfriend is probably behind you.

    I've written for Teen Vogue, Thought Catalog, Leveled Magazine, College Candy, How About We, and have been featured on several HuffPost Live segments. Creator and leader of Bold Moves October featured on xoJane and Neil Gaiman's blog. Both Neil and Jane appreciate boldness. I specialize in pep talks, very long bike rides, and matching my lipstick to my heels.