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Dating : Reuniting [28 F] with crush [31 M] of over 10+ years…good idea or bad?

Dating : Reuniting [28 F] with crush [31 M] of over 10+ years…good idea or bad?


I’ve secretly liked my brother’s best friend since I was a kid.

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We’ve known each other for almost 2 decades. I just got out of a relationship and he popped in my head again.

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He and my brother had a falling out…over something mysterious. Towards the end of highschool there was a lot of weird drama that went on. He used to call me all the time asking for girl advice about some girl he liked, and I talked to him giving him advice…feeling jealous, wishing it were me. I liked him a lot, it was painful. I was basically in love with him for 5 years. I let it go and went off to college, mostly forgot about it, had other relationships, and we never really talked to each other again.

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I’ve always wondered a bit…maybe..what if? I don’t know if I have feelings for him. I have no idea. I was way too shy to ever tell him I liked him, especially back then. It would have been weird, awkward (him being my brother’s friend and us knowing each other since we were kids), and I feared rejection.

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Well I recently reached out to him again…and I confessed that I liked him all throughout high school. He admitted that he secretly liked me too but was too afraid to say it. Apparently a lot of the weird drama that went on revolved around him secretly liking me. I had no idea.

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We are thinking of meeting up…but we are nervous. We don’t know if it’s a good idea. We basically haven’t seen each other in 10 years. But a decade..to both secretly like each other? We don’t really know what to do. I’m nervous. I think we are meeting up but I don’t know if we ‘should’. Thoughts appreciated.

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TL;DR: 28F and 31M secretly both liked each other in the past, confessed to feelings, now are in a place to meet up, nervous and not sure what to do.

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What do you think?

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  1. just treat each other as old friends who are now dating.

    but you do need to figure out what was the falling out in case you’ll have to make a decision about picking the guy or the brother…hopefully you don’t have to but you never know.

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