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Dating Best Friend's Ex?


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Posted

Yes, I realize I'm roughly the billionth person to ask this question, and the answer doesn't generally vary far from "No! Don't do it!" I'm aware that everyone thinks they might be the exception.

 

Still, I'm here. I'm asking because every situation is different, and my details match no one else's. I'm living with my two best friends, and I just got out of a 5 year relationship a few months ago. After my breakup one of my good friends from highschool comes into town (the girl of interest) and crashes at our place. Actually we were always friends, but my recent ex didn't like her, so we hadn't hung out with much frequency for the past few years. She's come back a few times now and starting on the second ocassion we've become romantically close, spending the days on adventure together (mostly platonicly) and kissing on a couple occasions at night.

 

The problem is one of those best friends I live with dated her in highschool for a few months (6 years ago).

Details:

-They dated for ~4months I think

-Occured 6 years ago

-She was his first girlfriend

-He's only dated 3 girls at this point

-I've known him for 11 years

-I've known her for 9 years

 

Oddly enough, there is a bit of precident. This friend's third ex dated a friend of ours that lives in a cottage in our back yard now. Yeah, I realize we were an incestuous group of friends (we figured that out in highschool). He never seemed obviously bothered by the situation (perhaps just a bit awkward). Still, I think of his two ex's, he was more romantically attached to the one I'm interested in (at least back then, don't know about now).

 

I know, I should have just talked to him sooner, but I was reluctant to risk friendship before I thought things were somewhat more serious with her. Naturally I would just ask him, but this is where I'm hung up at the moment. He can be a bit touchy and unpredictable. I can imagine him not caring, exploding or pouting for years, and I really can't begin to guess which I'll get.

 

My questions are:

Is the whole situation doomed? Should I ask at all or just let things go?

If I ask, how should I bring it up? What should I say?

I'd like not to shock him, but I'm not sure that's an option.

 

For the record, the friendship is more important by miles, not that she's anything short of fantastic. I'm just hoping for both (perhaps foolishly).

 

Thanks

Posted

Sounds like a fairly communal social structure to me so I'd say what the heck. You already pass off your best friend as unpredictable, which IMO is not a good foundation for friendship. OTOH, this girl may just be using you for an ego feed. Women dole out little bits of affection and attention, calibrated at precisely the right time and amount, to make men think they might like them and to keep the ego boost flowing. Be aware of that.

 

Have fun! :)

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Posted

Yeah, I don't mean to sound so negative about this friend. He's my oldest friend, and a fun and loyal one as well. He just has a handful of traits that don't suit this situation well. It doesn't help that I almost never talk about relationship stuff with guys, just girls.

 

Her using me as an ego feed concerned me a lot early on (and still does some). To be honest I think it's a component of any relationship up through marriage. I just wouldn't want to put anything on the line if it was just an ego thing. I think she hurt my friend in highschool by doing just that. Still, I feel she's been putting in a lot of effort with a messy situation I didn't expect her to want to put up with. She driven a hour each way on about 4 occasions to see me, says she's been interested in me for some number of years. She's very attractive and gets no shortage of attention in the town she lives in. The first time she came by, I could tell she was looking for a kiss, but I just went to bed trying to sidestep the situation. Still she'd call and came back to visit again. Admittedly, I don't consider myself all that charming or worth the trouble, but who ever does?

Posted

It took one of my wife's friends nearly two years of such displays of interest and attention, even in front of her husband, to finally wear me down to the point I thought she meant it. Women are brutal, man; just be aware. :)

 

IMO, if the social dynamics support this potential, go with that. Every situation is different.

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Posted
Women are brutal, man; just be aware. :)

 

Heh, yeah, don't I know it. The nightmare I suffered in the last few months of my last relationship could only be described as vicious, cold hearted, and spiteful.

 

Thanks for the advice. I'm trying to get up the nerve to talk to him today.

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