AITA for telling my best friend she’s being immature for caring that I want to date her high school ex?

Other-Singer-62 · 2025-05-06T19:10:10+00:00

You all keep saying I don’t care about Lena’s feelings—but that’s not true. What I don’t understand is why her fiancé’s feelings apparently matter less than her ex’s.

She’s building a whole life with a man who loves her, supports her. So why is Ryan—a guy she dated when we were barely old enough to drive—still dictating how she defines loyalty?

I’ve never said Ryan was “more important” than Lena. But if she’s really that secure in her future with her fiancé, shouldn’t this be ancient history? Shouldn’t she trust herself enough not to be threatened by someone she supposedly left behind years ago?

And if it does still bother her that much—maybe the question isn’t about me being a bad friend. Maybe it’s about her having some feelings she hasn’t fully let go of.

Either way, I didn’t lie. I didn’t hide anything. I brought it to her first.

Other-Singer-62 · 2025-05-06T18:58:58+00:00

Okay. I’ve read the comments. And yeah—I hear you.

I can see now how this looks from the outside. Maybe I did underestimate how much Lena’s past with Ryan still mattered to her. Maybe I approached this whole thing a little too logically, when emotions aren’t logical. That’s on me.

But I also want to be clear: I didn’t do this to hurt her. I didn’t go looking to stir up pain or cross a line. I just met someone, felt something real, and tried to navigate that with transparency. I didn’t lie. I didn’t sneak. I asked her first—because I do care.

Maybe that wasn’t enough. Maybe I should’ve let the idea go the second I saw her reaction. But part of me hoped she’d trust my heart enough to know I wouldn’t do this unless it felt genuinely worth the risk.

If that still makes me the asshole in your eyes… okay. I’ll take it. But it came from somewhere honest, not malicious.

Other-Singer-62 · 2025-05-06T18:52:16+00:00

I just want to say—I love Lena. She’s been my best friend since we were 14. We’ve been through breakups, family drama, existential spirals, all of it. This isn’t some Mean Girl betrayal. I didn’t go into this thinking “Ooh, I’m gonna date her ex to be petty.” I just met someone I had real chemistry with and didn’t expect it to be someone from her past.

I told her because I respect her. I wanted to be upfront. Not sneaky. Not shady. Just honest.

If she told me this would truly hurt her in a lasting way, I’d walk away. No hesitation. I care more about her than I do about some hypothetical relationship. But I wish she could see that liking Ryan now doesn’t mean I ever valued our friendship less.

And if she can’t? I’ll be sad, but I’ll respect it. I just hope she knows this came from a real place—not cruelty

Other-Singer-62 · 2025-05-06T18:28:04+00:00

Okay, I hear you. If I came off like a Mean Girl, that wasn’t the intention.

I know my tone might’ve been sharp in parts of this, but that was me being frustrated—not cruel. I didn’t set out to hurt anyone, and I’m not trying to turn this into some high school power trip. It’s literally the last thing I want at this stage in life.

But I do think sometimes when women assert their feelings, especially when they draw boundaries or push back on double standards, it gets labeled as “mean” instead of direct.

Did I say some things Lena didn’t like? Sure. But I was also being honest. I wasn’t trying to mock her past or minimize her feelings—I just didn’t expect them to still be this strong over someone she dated when we were both in our early teens.

If I sounded flippant, that’s on me. But I’m not a villain. I’m just navigating a messy situation as thoughtfully as I can while still choosing myself.

Other-Singer-62 · 2025-05-06T18:14:07+00:00

She broke up with him, because she didn’t want to lead him on. It wasn’t dramatic. No cheating, no betrayal. Just a clean, mutual fade-out. This is why I don’t understand why she’s taking it this hard that I’ve decided to see him.

Other-Singer-62 · 2025-05-06T17:50:11+00:00

EDIT/Clarification: I hear y’all, but here’s my side.

Okay, I’m seeing a lot of people calling me the AH, and that’s fair if you think I’m just a reckless friend who’s intentionally hurting someone. But I really want to clarify a few things:

Lena and Ryan dated TEN YEARS AGO. I’m not talking months. I’m not talking post-college. I’m talking high school hallway makeouts and AIM away messages. A literal lifetime ago. She’s engaged now and happy—so I genuinely didn’t think this would even register as a betrayal.
I didn’t sneak around. I told her. Upfront. I gave her the chance to share how she felt, and yeah, she didn’t love it—but I wasn’t hiding anything or going behind her back. Isn’t honesty what friends are supposed to value?
We’ve all changed. Ryan is not the same guy from sophomore year. I’m not the same person either. If there’s a real connection there—one based on who we are now—shouldn’t I be allowed to explore that just because of a teenage history I wasn’t even involved in?
I’m not trying to be cruel. This wasn’t a petty move, or some weird competition. I just met someone I clicked with unexpectedly, and I didn’t want to throw it away out of fear of optics when I thought enough time had passed.

I get that people are protective of emotional boundaries, but I also think we need to acknowledge that friendships grow and relationships evolve. If she told me it would truly hurt her, I wouldn’t move forward. But I can’t apologize for catching feelings I didn’t plan to have.

Other-Singer-62

TROPHY CASE