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Parallax - Advice

April 2, 2001

Best friends forever?

Dear Conversely,

Ask us a Question!How can I turn an old friend into my new boyfriend? I have feelings for one of my dearest friends. We're both twenty-five and have known each other for four years. He has his friends and I have mine, but we usually hang out together - just the two of us. We're very comfortable around each other and have a lot of fun. We've always jokingly flirted, but lately I picked up more serious signs. The other night we were hanging out and having a good time when he asked me to make out. After a few minutes of awkward kissing, we both gave up. It's been almost a week, and although we swore we wouldn't get weird on each other, we haven't spoken. I have to hang out with him soon or I'll risk losing his friendship. I want to know how to act when I see him and if he likes me or sees me as a convenience (he's never had a girlfriend and I don't want a casual relationship). I've sensed jealousy from him when I mention other guys (he doesn't like any of the guys I date), and if I say I have a date on Friday, he'll get competitive and say he has one on Thursday. I don't think I'm attracted to him physically - I never really thought of him that way. I'd sure appreciate your help. Email to a Friend

Her view:

Dear Girlfriend,

Well it sounds as though you're curious about this guy. The real question is, 'Do you think you might become physically attracted to him?' If the answer is no, then this relationship should never get started. Here is your risk factor: you may need to fool around a bit to find out. If you discover that you're not interested, you might destroy a great friendship. I'm sure you're thinking that your friendship will be saved if the boyfriend thing doesn't work out, but you are more likely to win the lottery than have your friendship return to normal after having sex (or the like).

Having said that, if you are emotionally drawn to this boy (and like him enough to fool around a little) I think you've got a shot. It takes a physical attraction to get you to the next level of 'like' - the 'like him for who he is as a person and all the things about him' that make the two of you great friends. At that point you'd be ready, so you could just pull in the physical and have a great relationship.

It's a risk. You have to be willing to lose him, but you should give it a shot if you think you can get there. Of course he has to want all of this too and you need to be sure before launching in. Why don't you get a little blunt and talk about it. Go out casually one night and bring it up. Talk to him about it as if he was some other guy - the difference is that this time, it's him. Discuss it as a hypothetical situation. Say, 'Imagine if we dated...' I think you'll get enough data to make a decision.

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His view:

Dear Girlfriend,

You don't want to turn anyone into a boyfriend. Stay away from whatever clever tactics my colleague suggests - I'm sure she has no idea as to what is going on here.

The problem is your 'would-be boyfriend' is going through a very basic dynamic that often occurs in male-female friendships when the platonic line is only vaguely drawn. He's the guy who doesn't really want to date you because he knows the friendship is worth more. However, he still gets jealous because he doesn't want to see you with someone else. It will make him feel lonely and you won't hang out with him as much. He'll also be constantly reminded that you have someone and he doesn't. But - and here's the catch - the moment he finds another girl, he won't be feeling too bad about you.

If you try to turn him into something else, it will backfire. The best thing to do is draw a very clear line for him. The only way he can cross it will be by wooing you and winning you, not by propositioning you for a quick-and-rough make-out session whenever the urge strikes him.

I don't think he's a bad guy: he's not out to get you for convenience alone. But if you are in deeper than him you are going to get hurt, unless you start setting down the rules.

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