Should I Set Boundaries with My Friend Wanting to Date My Ex?

A 29-year-old woman is trying to keep her life peaceful after a breakup, and then her “just friends” situation gets messy fast. She and her ex, Mark, ended things amicably, and they even agreed to stay in each other’s lives. Sounds mature, right?

But her friend Sarah, 27, has been acting different for a while. She keeps bringing up Mark, asking pointed questions about their history, and generally hovering around the details of the relationship like it’s her business. Then last night Sarah finally confessed: she’s into Mark and wants to date him.

Now the whole friendship feels like it got a trapdoor under it, and OP is left wondering if boundaries are about feelings or about fairness. Here’s the full story.

Original Post

So I'm a 29F and recently broke up with my ex, Mark (30M). We ended things amicably but decided to remain friends.

Enter my friend, Sarah (27F). Sarah knows all about my past with Mark, the good, the bad, and the ugly.

She was there for me through the ups and downs of our relationship and breakup. Lately, Sarah has been acting strange, always bringing up Mark in conversations and asking pointed questions about our history.

Last night, Sarah confessed that she developed feelings for Mark and wanted to pursue a romantic relationship with him. I was completely blindsided and hurt by her admission.

I opened up to her about my struggles post-breakup, and now she wants to date him? It feels like a betrayal of my trust and friendship.

I value both Sarah and Mark in my life, but I'm not sure if I can handle them being together. I'm torn between wanting my friends to be happy and feeling like boundaries have been crossed.

I understand feelings are complicated, but is it too much to ask for them to respect my feelings too? So, would I be the a*****e for setting boundaries with my friend, Sarah, about pursuing a relationship with my ex, Mark, considering all she knows about our past?

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This is similar to the AITA where someone set up their best friend with an ex who broke their heart.

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OP thought staying friends with Mark was the “safe” choice, until Sarah started peppering her with questions about their past like she was auditioning for a role.

After Sarah’s confession that she wants Mark romantically, OP’s hurt hits harder because Sarah was there for the breakup, not in the “distant acquaintance” way.

The real tension kicks in when OP realizes she might not be able to keep both relationships comfortable if Sarah and Mark actually start something.

And once Mark is back in the picture through Sarah, OP is stuck deciding whether setting boundaries is protecting her heart or ruining a friendship that used to feel solid.

We're curious to hear your perspective. Share your thoughts in the comments.

If Sarah can’t respect OP’s trust after all that breakup-history, then Mark dating her might not be the happy ending anyone thinks it is.

Wondering if dating your best friend’s ex is worth the loyalty fallout, see this Reddit moral dilemma about dating a best friend’s ex after a messy breakup.