Should I Date My Friends Ex? The Dilemma of Love and Loyalty

A 28-year-old woman is trying to do the right thing, but her love life keeps stepping on landmines. Her longtime friend, Sarah, just broke up with her boyfriend of years, Chris, and now Chris is looking at OP like the “what if” he should have acted on sooner.

Here’s the twist: Chris told OP he had feelings for her even before Sarah and Chris officially called it quits. They’ve gone on a few casual dates, and the connection is real, but Sarah has been distant, still processing, and OP hasn’t told her because she’s scared it will sting even more.

And the real question is whether dating Chris would make OP the villain in a friend group that’s been tight for over a decade.

Original Post

So I'm a 28-year-old woman, and recently a close friend of mine, let's call her Sarah, broke up with her long-term boyfriend, Chris. Chris and I have always had a great connection, and after the breakup, he confessed to me that he had feelings for me even before they broke up.

I was taken aback but couldn't deny the spark between us. We have gone on a few casual dates, and things seem to be heading towards a relationship.

Sarah has been a bit distant lately, and I know she's still processing the breakup. I haven't told her about Chris and me because I'm afraid it will hurt her even more.

On one hand, I don't want to hide my feelings or potential relationship, but on the other hand, I don't want to betray Sarah's trust or hurt her further. Could pursuing a relationship with Chris make me the a*****e in this situation?

Quick context: Sarah and I have been friends for over a decade, and Chris was also part of our friend group before they started dating. I value both of their friendships and don't want to jeopardize that, but I also can't ignore the connection I have with Chris.

So WIBTA for pursuing a relationship with my friend's ex despite their interest in me? I honestly don't know what to do.

The Complicated Web of Feelings

This situation is a classic example of how love and loyalty can clash in unexpected ways. The OP's feelings for Chris, which predate his breakup with Sarah, complicate matters even more. It raises the question of whether it's fair to act on a spark that’s existed while Chris was still in a relationship. This lingering emotional tension is bound to create friction not just between the OP and Sarah, but also among their wider friend group. If the OP pursues Chris, the fallout could lead to a rift that might never heal.

Moreover, the fact that Chris has confessed his feelings adds another layer. It’s one thing to explore new relationships; it’s another when those feelings are built on a foundation that also involves betrayal towards Sarah. This isn’t just a romantic dilemma; it’s a test of the OP’s values and loyalties.

Comment from u/TheCuriousCat

Comment from u/spicy_pickles_99

Comment from u/birdsong27

OP isn’t just dealing with a breakup, she’s dealing with Chris confessing his feelings right after Sarah and him ended things.

While OP and Chris are on casual dates, Sarah is pulling away in a way that makes every conversation feel like it’s one step from a blowup.

It’s the same kind of moral mess as the dilemma of dating a friend’s ex when feelings are mutual, where honesty can still blow up friendships.

Why the Community's Reaction Matters

The Reddit thread sparked a heated debate, showcasing the community’s divided opinions on this kind of situation.

Comment from u/purplemoonlight_

Comment from u/TheRealDuckie

The fact that Chris’s feelings started before the breakup turns this from a “new beginning” into a potential loyalty nightmare for OP and Sarah.

And because Chris used to be part of their shared friend group, any fallout won’t stay between two people, it will splash across everyone.

What are your thoughts on this situation? Share your perspective in the comments below.

Final Thoughts

This story serves as a reminder that love can often complicate our relationships with friends, leading us to question where our loyalties lie. The OP is caught in a moral quandary, weighing her feelings for Chris against the potential fallout with Sarah. It’s a tough position that many can relate to. So, what would you do in this scenario? Would you pursue your feelings, or prioritize your friendship?

The Bigger Picture

In this situation, the 28-year-old woman finds herself in a classic love-versus-loyalty dilemma after Chris, her friend Sarah's ex, confesses feelings he had even before the breakup. The emotional connection she shares with Chris, complicated by Sarah's recent distance, creates a challenging landscape where she's torn between pursuing her desire and protecting her long-standing friendship. By choosing to keep her relationship with Chris under wraps, she’s trying to navigate the potential fallout, illustrating a common struggle where romantic interests can threaten to disrupt established friendships. Ultimately, her hesitance reflects a deep understanding of the complexities involved in intertwining romantic and platonic relationships.

If OP chooses Chris, she might not just change her relationship status, she could permanently change her friendship group.

Before you make a move on Chris, see what Reddit users said about Sarah’s friend-ex triangle in is it wrong to date a friend’s ex.