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Parallax - Advice            June 12, 2000

   He's been waiting for her for more than a year...

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I've liked this woman from work for a long time, at least a year and a half. She was always off limits because she was seriously dating this guy and they were engaged. I just found out that they've broken off the engagement, and they're no longer dating. I'm reasonably good friends with her and I've offered her the usual words of support, etc. But I really feel that if there's ever been a chance for me, for us to have a relationship, this would be it. What do you think, and should I give it a try?

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Her view:

Dear Gambler,

Yes, but be very calculating. She has just broken up with a fiance and no doubt will be licking her wounds for a while. You tread a thin edge between jumping in too soon, or waiting and allowing possible competitors to move in - so the timing needs to be just right.

Give her some time - say four weeks - and be a great friend to her. There is no better way for her to notice what a fantastic guy you are. Support her in every way you can - exceed her expectations without making a move. She'll calm down about the break up in time and then you can foray. But don't wait too long, as other little sharks will move into your well-staked-out territory - if she's as great as you think she is there will always be other guys hanging around.

There's a lot of groundwork you can lay during the interim period. Take up a lot of her time by being a great friend. This will limit her exposure to other suitors. Show her how fabulous and fun you can be without the pressure of dating. Then, when you feel the time is right, tell her about your feelings - or just go for a smooch - and let things take their natural course.

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His view:

Dear Gambler,

This is a love gamble, and there's really only one way to play it. But I have to say, the odds are not in your favor.

Stay the course on the friend tack. But keep it strictly friends, and don't let her see you have any other intentions. (This is risky proposition #1: if she sees through you, you're toast.)

Essentially, you become the confidante - you want to be close enough so you can recognize when she's ready to start dating again. But don't make your move just then, unless you want to be rebound man. (Risky prop. #2: if you become rebound man, she might just dump you as rebound men usually are.)

When she starts seeing a new guy, make sure you can exert enough influence to get rid of him if things start getting too serious. (Risky prop. #3: if you can't, her 'rebound man' may turn out to be more than that.)

Once you deem her ready for real love, you can nudge her in your direction - but this will work only if you play things cool enough all along, if you become as important to her as she is to you. (Risky prop. #4: if you don't, get ready for some painful backpedaling).

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