The Hook Up: How to deal with intense heartache


Basically, there is this girl. I think she’s super pretty and she seems really cool. The only problem is, I’ve never actually had a conversation with her. However, over the past few weeks ,my little crush has really been driving me crazy.

I really want to ask her out on a date or something, but I also don’t want to look like a creep. I’ve debated messaging her on Facebook, but then there is the fact that I gave my number to one of her friends at one point and got rejected, so I don’t want to look desperate or creepy considering we’ve never actually talked before. I just don’t want to wait around and miss my opening to make a move, but I definitely don’t want to get rejected because I came on to her in a weird way.

We do have a lot of mutual friends, so I feel like they could maybe say something to her about me, but at the same time that could also come off weird because then I look like I’ve been stalking her and now I’m resorting to my friends to get what I want. I know I have to put myself out there to really get anywhere with her, but I want to do it in then most non-creepy, somewhat attractive way. How should I go about this? — Crushing

Anna says: Well, it’s hard to ask someone out in a non-creepy way if you’ve never actually spoken to them. Your problem seems to be a classic case of putting the U-Haul before the horse. Before you worry yourself sick trying to come up with the best, most perfect come-on line that will woo her into a love-sick stupor, you should realize that such a thing doesn’t exist. Focus instead on, you know, actually getting to know her before you even think about asking her out. If Facebook is easier for you to establish that first connection, then use that. Send her something like, “Hi, I’m Crushing. We have all these mutual friends but you and I don’t actually know each other. I think this should change. Also, [some relevant detail from your lives that will establish commonality] and [a casual question that will up the chances of her responding to the message]?” Etc.

Once you start talking to her, you’ll be far better equipped to gauge whether the feelings might be mutual, and whether you even like her enough to ask her out in the first place. She might seem pretty and cool from a distance, but you won’t know if you’re compatible until you bridge that oh-so-important communication gap. You’ve got the guts, now go make the leap.

Whatever you do, don’t get your friends to do your dirty work. That is, as we say in Ashtanga yoga, incorrect method. Good luck!

Hailing from the rough-and-tumble deserts of southern Arizona, where one doesn’t have to bother with such trivialities as “coats” or “daylight savings time,” Anna Pulley is a freelance writer living in San Francisco. Find her at and on Twitter @annapulley. Send her your Hook Up questions at

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