From: Derek

Unfortunately, I’ve fallen in love with one of my best friends. I really want to go out (but hook up to spark the relationship) with her, but I don’t know how to start. Ever since she broke up with her boyfriend, she’s been texting me more and always seems to want to hang out with me. I can get her alone pretty easily, but I don’t know whether to risk trying to hook up with her, because if she doesn’t feel the same, that’d make it real awkward between us.

She keeps throwing me mixed signals, like asking me to take her out, then when I take her out, telling me she want to hook me up with one of her friends.

So first, do I try to hook up with her? And second, how should I start when I get her alone. Thanks.

H.U.S.H. Response:

Lots of dudes wind up with a crush on one of their female friends. It feels uniquely unfortunate but actually it’s a universally awkward experience.

Step One, you have to weigh out whether risking your friendship is something you ever want to do with this girl.

On the one hand, keeping it inside could feel like a burden and never knowing what could have been might be a frustrating experience. Some people wind up with their soul mates through romance with a friend. Some people wind up with a fun fling for a brief period of time but then lose that friend forever when the relationship falls apart.

It’s up to you to decide if this is something you are ready to risk. But if the answer is “yes” you have to go for it.

If you two are alone look for an opportunity to make a move that would work with someone you weren’t already friends with. Cuddling up while watching a movie. Sneaking away together at a party for some fresh air. Hanging out alone at one of your house and goofing around in a physical manner (tickling, thumb wrestling, playing with your food, whatever). If you’re alone and you sense a tension you’re basically looking for an opportunity to go in for a kiss. Prolong light touch (a hand falls on a knee or someone’s head rests on the other’s stomach during a picnic somewhere). Keep up lots of eye contact. Allow for lulls in the conversation that you could transition into leaning in for a liplock.

If it doesn’t go well and she dodges the kiss that’s okay. At least then you have a better idea where she stands on this idea of you two being more than just friends. Things you could say.

• Hey, I must have misread some signals and I thought you were interested in something else.
• I’m sorry. I’ve just found myself really attractive to you and really felt like I needed to act on that but I totally get and respect if you don’t feel the same way.
• Laugh it off lightly (as though you had just tripped and fell). That was stupid, but I thought maybe that’s what we were leading to.

BUT – you don’t have to go for the hook up initially to make this happen. If you two are alone and the mood is obviously romantic (your hands are touching for a long period of time, you have lots of flirty eye contact, it’s quiet and you both find yourselves anxious for what comes next) you can start a conversation about this instead. I get it – maybe moving this to the next level by hooking up and then figuring things out seems like an easier approach (and it is the way lots of couples are started) but it’s not the only approach. You do have the option to talk first and take your clothes off later.

Don’t frame it as: I’ve had a big crush on you. I’m in love with you. When can we date?

Instead try to say more things like:

• I’m finding you really attractive lately and I want to do something about it.
• It’s been really hard for me lately not to kiss you.
• So I always have fun and enjoy myself around you but I lately I’ve also been finding myself really physically attracted to you.

Words can work just as well. So consider your options and make a move!

Thanks for reading and I hope some of this helps,

H.U.S.H.

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