I have a crush on my ex boyfriend's best friend?

So this guy was in almost all of my classes this last year, so naturally, we became the best of friends. Then we decided to screw things up by dating for a few months. I soon broke it off because I missed being just friends. Now we're pretty distant. He tries to reach out sometimes, as do I, though since we broke up things have been (for lack of a better word,) awkward.
The next few months, I begun getting closer and closer with one of his best friends, also one of mine that I was friends with in primary school then drifted from in junior high. We talk and text a lot. We always tease each other and have a generally healthy friendship.
I am so scared because I'm starting to get feelings for him, and it feels as though history is repeating itself. (Even though this is a different situation because it is indeed a very different friendship than the one I had with the other guy)

My other issue is that I'm afraid my ex/now friend again will become angry and his best friend and I if we actually do date.

My final issue that I can think of is, what if I do end up dating this guy, and then we break up, and I'll have once again landed in this awkward stage with someone I was once so close with.

I appreciate any and all advice. Thank you for taking your time to read and/or respond to this.


Most Helpful Girl

  • Honestly, I wouldn't do it. I know that it's tempting, but the cons are too great. You shouldn't want to date someone in the same circle as your ex, let alone his best friend. It can get messier than you'd intend it to, especially it you guys were to break up. Its just not worth it. There's plenty of other dudes out there :)

    • Thanks for your opinion, I really appreciate it! :)
      I don't know though. I really like THIS guy. I'll try to see if the feelings pass, as that does happen to me often. :)

    • No problem! Good luck out there :)

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  • Well first of all, when dating there are two outcomes, you get married and maybe like happily ever after or you dont. Whether its a week or 20 years you never know, its part of the risk, so on that front, i would say, go for it. Secondly, on the "my ex's best friend" front, i would say, who cares? Its awkward between you two and you are both distant, do you think it really matters if he gets pissed? He will get over it, 100% positive of that. In my experience when i was in a good relationship my past relationships were irrelevant. Just my opinion. Good luck, i say go for it. :)
    P. s. although you make up your mind, he may not be willing to cross that line with his friend. So just play it cool.

  • It may be a daring move but... perhaps you should speak with your ex about this? You are attempting to be on good terms with him, so you should be as honest with him as you can. If you truly have feelings for this other boy, than you may regret it more if you don't pursue it. If history does indeed repeat itself, then that's the way it is. These things can happen in life sometimes, but that does not mean it will happen every time.

    If anything, ask yourself if you will regret never confessing to this boy more than being honest with him, your ex, and yourself.

    It is up to you :)
    Best of luck!

    • Thank you!!! <3 xx Your response really made me think.

    • it's no problem :) i hope everything turns out well for you!

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