He says, she says, volume IV

Dear Steve and Ari:

I have this friend. I find her extremely attractive, but I don't want to try and initiate something and then lose out on her company. We get along really well and always have entertaining conversations. On the other hand, it's kind of hard to tell what she's feeling because, as a rule, she's friendly with everybody.

To complicate things, she's 34 and I'm 18, which is a revelation for everybody who meets her. The first time I met her my guess was 24. To give the situation some context, we're both in the same film program at a technical school. She comes over and hangs out at my place with a few of my other buddies after the shoots.

Based on my best judgement (that is, probably not great), I have the best chances out of all of us. So, like I said, I really enjoy her friendship, but I would like to give dating a shot. How to ease into that? Suggestions?-Justin

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Ari says:

Justin,

she's 34 and you're 18. I see. And what are you hoping for with a person almost 2x your age? If you want a relationship, I'd say it looks grim. I mean, your pop culture references are all off, you can't go out drinking with her... not a good sign. I think in the end the large berth of age difference will doom you both. If you want to be her friend with benefits, I say the odds here are TOTALLY in your favor. As a 32 year old woman, I'd love {!!!} to play with an 18 year old. I'm also willing to bet she'd be one of the best lovers you've had and vice versa.

Keep in mind too that you are together a lot because of school - you will have to see her a lot still, try not to embarrass yourself or create awkwardness that is insurmountable. I'd suggest you strive for a physical friendship.

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Steve says:

Justin,

First off, your goal here is not to "ease into" anything. You are much younger than this girl, and if you want her to think of you as an equal, you're going to have to show an inordinate amount of confidence. Abandon all pretense, and go for it with guns blazing - or don't go for it at all.

Ask her out. Invite her to dinner, or offer to cook her something at your house. Ask her to go someplace specific, with you, so she knows you aren't just asking her to hang out with the gang.

Pay extra attention to how you talk to her. Never say "um", "er", "uh", and so on. Be polished.

Be assertive. Be decisive. Take control of the situation, whether it's a blowout on the highway at 60 MPH, or the group arguing about where to go for donuts at 3:00am. When you take charge, she'll notice. Believe me. There is a chance she thinks of you as nothing more than a snot-nosed kid, and it's your job to erase that.

One other thing - and you mentioned this yourself - be sure this is what you want, because if it doesn't work out, you might not have her as a friend anymore. Personally, I'd go for it.