AITAH for liking one of my best friends’s ex from 10 years ago?

Am I the asshole for liking one of my best friends’s ex from 10 years ago?

I’m F25, my friend is F24, her ex is M26

My close friend dated a guy in high school for about one year, he broke up with her because he was one grade older and going off to college. This guy was her first boyfriend, (“first love”, if you will) and sometimes he was a bit of an ass (lazy, rude, hornball) but we were kids. It was definitely not right for him to act that way, but jeez, we were 15 and 16 years old.
He is now 26, and I don’t feel he is the same person at all.

I stayed best friends with her, I have known her since middle school.

I recently connected with him M26, and we had instant sparks and great chemistry. A person can change a lot in 10 years. I feel it is unfair to compare a 16-year-old‘s actions to a 26-year-old man. I’ve gotten to know him again and he is much different as an adult, and we have a genuine connection.

It’s very important to know that my friend F24 CURRENTLY has a committed relationship of three years with a new guy. So, I didn’t think it would be a problem if I reached out to tell her.

I texted her stating he asked me out and what her thoughts were on that. I just wanted to be honest because she is my friend, and she should hear it from me. He is still “an ex” even though it’s been so long, I just wanted the green light.

Long story short, she takes two days to reply back, and ends up saying she’s NOT comfortable with it, and it would hurt her if I pursued him.

She also feels it is “not right to date anyone’s ex regardless of how much time has passed”
She also stated she “will forever see him for what he was when they were together”

Honestly, this crushes me, I really want to respect her feelings, but I can’t help but feel this is a bit unreasonable. It also breaks my heart feeling like I have to choose between them.

If I did theoretically pick her, I would look for this guy in every person I meet, and always think about what my life with him could have been.

If I did theoretically pick him, I would probably lose one of my best friends over a guy from 10 years ago. And it would likely cause drama in my friend group.

I truly did not think this would be an issue because it was a whole decade ago. We were kids. And, because she has a new long term relationship… Is my new relationship with him even any of her business?

It feels selfish of me to say, but I really just want to be happy, and I don’t know what to say to her.
I really didn’t want to hurt her, but I think I have.
It was not my intention to cause any drama, especially high school drama at my big age of 25.
Am I in the wrong? AITAH?

14 thoughts on “AITAH for liking one of my best friends’s ex from 10 years ago?”
  1. I don’t really consider casual Highschool dating relationships as an Exes, as you were kids back then. So IMO you’re not an AH if you date him. You friend is unreasonable IMO

  2. So, your friend thinks that she should have veto power over your relationship with anyone she’s ever dated, even a decade after the fact and a guy she dated for only a year?

    Life doesn’t work like that.

    Oh, you are definitely NTA.

  3. Very mild YTA for asking her for her input. For your friend, it’s not about how much time has passed, it’s about how things ended. He broke up with her and he was a jerk to her. It could be 20 years later and that’s all she will remember about him.

    You’re not wrong for seeing that he’s a different person and that people change. You thought your friend would be fine with this and she is clearly not fine. But you put yourself in this position when you reconnected with him and when you asked your friend for her input.

    So, what’s worth more to you? Your friendship of many years or the possibility of a future with this guy?

    1. This. It’s different from the usual high school exes thing since it was her friend’s first love as well so that usually has a way deeper impact.

  4. Why did you reach out to her in the first place?

    You asked, she answered. You now get to decide what to do. If you go out with the guy and he turns out to be the one, will your friend really be upset about it? If so, is she really that much of a friend? Even if you don’t continue the relationship with the guy she will cool to you so you might as well continue dating.

    What you probably should have done is go out on a few dates to see if there is a connection before telling her.

  5. I would say you’re NTA but I wouldn’t date any of my friends ex’s especially first loves, feelings aren’t rational and I’m not surprised she’s uncomfortable at the idea of it. And if he broke up with her she probably had to deal with the emotional fallout out of still having feelings for him and it not working out due to circumstances. But everyone else in the comments are right you’re all adults so you can do as you please. But I don’t think your friend is an asshole either, hopefully she’s able to come down to earth and realize it’s really not that big of a deal. 

  6. Is this guy really worth loosing a friendship over? Or is your friendship worth loosing for a guy? Do what you want but you’ll likely lose one in the process so a good time to sit down and see what your willing to lose.

    Realistically you haven’t known this guy that long, so you cant 100% judge if he doesnt have any old tendencies from his teen years. Yes people change but old habits, ya know?

    Second it might be worth asking her why this makes her so uncomfortable. Especially since you said he was a “hornball” is there an event or trauma that made her decide she doesnt want to be around him anymore? If you got serious with him, she’d eventually have to be around him if she stayed your friend, that would feel like being forced around a bully depending on how he treated her.

    As of right now NAH but I think you should dig more into why this bothers her. 

  7. NTA, in my opinion.

    As you stated yourself, a person can change DRASTICALLY in a decade, especially if that decade was a shift from middle to being a full-blown adult.

    While you said he was a bit of an ass back at that age, most kids were. He didn’t do anything abysmal to her, and, honestly, him being upfront to her about why he broke up/realizing long distance wouldn’t of worked for him then is one of the more mature breakup reasons I’ve heard, especially from a teen boy.

    Also as you said, you deserve happiness. If it comes in the form of him, that’s no fault of your own.

    In all honesty too, I think your friend not letting go of a relationship that old, especially given the context of the relationship (time in life, how it ended, etc) AND she has a “new” long-term partner, is rather unhealthy on her part. I’d say there’s probably something unresolved on her end (whether it be insecurities or immaturity) and she’s projecting that onto you.

    That’s just my two cents, but I can’t ultimately advise more than for you to go with your gut.

  8. Wait- let me understand.

    You asked your friend about this because you wanted her opinion. She gave you her opinion. You don’t agree with her thoughts, and now you feel some type of way because this man is (I’m assuming) the love of your life who you would look for in every other man?

    You caused this problem, not by wanting to date her ex from high school, but because you reached out making this like you respected her opinion when in reality you don’t like the answer.

    It’s okay to disagree. You two should sit down and have a serious conversation, not done through text. But realize that you went about this the wrong way. Don’t frame it like you want her opinion when you only wanted her acceptance.

    I don’t think there’s anything wrong with you seeing her ex of 10 years ago. But now that you’ve opened this can of worms, you should hear her out as to why she doesn’t want you to do this.

    YTA- don’t ask for someone’s opinion if you’re not ready to hear it

  9. I can’t imagine caring about who my HS ex dated. But don’t ask for permission if you don’t want to take “no” for an answer. Now she’s going to be pissed off because you are ignoring her wishes. NTA, but this probably won’t end well.

  10. NTAH Buuuuuttttt
    You asked permission. Mistake. You could have worded it different by making it more of a statement. “I just wanted to let you know that…”

    Your statement about looking for him in every guy you meet in the future, is a bit over the top. Do you really feel like every potential mate will have to be compared to this guy? That seems a bit obsessive.

    Bottom line, ask yourself a few questions. Am I ok losing this friendship? Do I think my friend will some day get over this? Can I get over this guy?

    There is no way to make this work without someone feeling some pain. Start from there and figure out where you are comfortable directing that pain. Stop justifying this situation with statements like, she is in a LTR with another guy. That’s just trying to let yourself feel guilty. This is about you and your choices.

    Life is hard.

  11. ESH. Her because you’re right in that no one is the same person at 26 as they were at 16. You because she’s right that you do not date your friends exes. And you were clearly not actually asking her, because her “no I am not comfortable with this” took you so aback you’re willing to dumb a decade-old friendship for a guy you’ve been chatting to for a few weeks. And what happens if you dump this friend, start dating this guy and then it turns out he actually is still a jerk? You’ve lost your friend (and probably more friends alongside) and now have no one. Yeah he may have changed. He also may not have done so. How convinced are you? Especially given that he’s still on his best behaviour and not showing you his true self.

    Also, “I would look for this guy in every person I meet” is incredibly dramatic. How long have you known this man? And you’re already talking like he’s the love of your life you tragically lost at sea? He may have moved on since he was 16, but have you? Because you are not talking about this like a rational adult.

    Look, you may be right. He may be your Prince Charming and worth throwing away your friendships over. But how sure are you? How much are you willing to gamble on this?

  12. YTA – don’t ask questions you don’t want to know the answers to. You’ve set yourself up for an impossible choice, but here you are.

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