📝 AITA for never telling my best friend that her fiancé hit on me years ago?

By aitahelpthrowaway38 • Score: 2 • April 24, 2025 6:55 PM


So here’s the backstory: I (29F) have been best friends with “Tasha” (30F) since high school. Ride or die. Shared beds on vacations, bailed each other out of everything from bad dates to job interviews. She's like a sister—if your sister occasionally Venmo’d you for weed money.

Now, five years ago, I had a fling with a guy—we’ll call him Derek (32M). Nothing serious. Hooked up a few times, fizzled out. No big deal. About a year later, Tasha meets Derek at a party, not knowing we ever had a thing. I tell her, she asks if I mind her going for it. I say nah—it was casual, ancient history. I meant it.

They start dating. It gets serious. Then engaged. Here’s where it gets weird: about six months into their relationship, Derek drunkenly messages me on Instagram at 2am. Something like: “Do you ever miss what we had?” and “You’re still the hottest girl I’ve been with.”

I screenshot it. I freak out. But I don’t reply. I don’t tell Tasha.

Why? Because it never happened again. He never brought it up. He acted normal from then on, like it never fucking happened. She was so happy, finally in a stable relationship after years of dating unstable men. I didn’t want to destroy that over one drunken slip.

Now they’re two months away from their wedding. I still have the screenshot saved. And it’s eating me alive.

Part of me says: “Tell her. She deserves to know who she’s marrying.” The other part says: “It was a few messages, five years ago. He clearly chose her, not you.”

If I tell her now, I nuke her wedding. If I don’t, I stand there smiling while she marries a guy who once tried to crawl back into my DMs.

AITA for staying quiet? Should I tell her?

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