Should I Date My Best Friends Ex? Navigating Post-Breakup Boundaries

He thought the hardest part would be watching his best friend, Amy, get through a brutal five-year breakup. Turns out, the real plot twist is the moment he starts catching feelings for the guy she just lost, Jake.

Now it’s not just “supporting a friend,” it’s Amy confiding in him about her feelings while he and Jake quietly realize they have chemistry. Jake has even said he’s interested, and OP is stuck between wanting something real and worrying he’ll crush the trust Amy has been handing him like it’s fragile glass.

And the worst part? OP is debating whether to tell Amy first or keep it secret, which could turn a friendship into a battlefield fast.

Original Post

So I'm (27M) and my best friend, Amy (26F), recently went through a breakup with her long-term boyfriend. They were together for five years, and the split was tough on both of them.

Amy has been confiding in me about her feelings, and I've been there to support her through it all. As time passed, I started developing feelings for Amy's ex, Jake (28M).

We've always gotten along well, but I never saw him in a romantic light until now. We share similar interests and have a strong connection.

Jake has also expressed interest in me, and we both feel a genuine connection that we want to explore further. However, I'm torn because I know Amy still has feelings for him, and I don't want to hurt her by pursuing a relationship with Jake.

I've been debating whether to talk to Amy about my feelings for Jake or pursue something without her knowledge. I care about both of them deeply, and I don't want to betray Amy's trust or jeopardize our friendship.

So, Reddit, would I be the a*****e if I started dating my best friend's ex, knowing she still has feelings for him? I honestly don't know what to do in this situation and need some outside perspective.

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This gets messy fast like the Reddit debate over loyalty and romance after a best friend’s “messy breakup”.

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While Amy is still processing the breakup with her long-term boyfriend, OP is over here realizing Jake is suddenly “romantic” to him too.

That’s when Jake’s interest becomes more than a random coincidence, especially since Amy has been sharing her emotions with OP.

The timing gets uglier because OP is considering dating Jake without telling Amy, even though he knows she still has feelings.

So every move OP makes, whether it’s bringing it up or staying quiet, could blow up the friendship with Amy and the connection with Jake.

What would you do in this situation? Share your opinion in the comments.

If OP waits too long, he might end up losing Amy and Jake at the same time.

Still torn about dating Amy’s ex Jake after the breakup, see the AITA verdict in this case about dating a best friend’s ex.