Dating an old high school friend

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Ashley: We hooked up for a semester in college, then spent about two years being mostly just friends again while he did an internship in NY (I was still based in Indiana) then moved to Seattle.

After a year in Seattle he came back to Indiana to visit, and we decided to try and date for real. Ashley: We talked so much about every decision and all of our feelings so that even when it felt weird, it quickly went back to not feeling weird.

When we broke up nine months later, all the usual post-breakup awkwardness and bitterness were multiplied tenfold by the fact that we were forced to hang out whenever our families got together, which was often.

On the flip side, when we rekindled the flame after college, our friendship and the friendship between our families became one of the best parts about our more-than-friendship.

If you found someone who thought you were beautiful in braces and side bangs, never let that person go.Dating a friend is widely recognized to be a pursuit fraught with potential complications.If it works out, great — but if it doesn’t, well, there’s a good chance the friendship won’t survive unscathed.Ashley: We met in a seminar that was set up like a production company, and I was his boss. About a year later, after ending a terrible relationship and getting fired from my job, I went to a party at his house.He asked if anybody wanted to go four-wheeling, and I said I did. Kelly: She didn’t really know it was supposed to be a date. Ashley: I’m bisexual, and if this were true, I wouldn’t have any friends. And I have been attracted to most of them at some point or another, just not in a way that I could or wanted to sustain. Kelly: I think that viewing relationships as an inevitable thing that happens between two people who are attracted to each other takes away from the emotional vulnerability, and work, that goes into building strong commitments.

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