Should I Confess? Dating Friends Ex Behind Their Back

Is it ever okay to date a friend's ex behind their back? OP faces a moral dilemma after accepting relationship help from a friend and falling for her ex.

A 28-year-old guy thought a “harmless” setup could lead to something real, until the person in the middle was his best friend’s ex. OP and Sarah have been close for over five years, the kind of friendship where you know each other’s patterns, not just each other’s names.

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Sarah offered to set him up with Mark, her ex, and they hit it off fast. Two months later, OP is dating Mark, feeling it’s special, and still keeping it a secret from Sarah. That secrecy is the whole problem, because Sarah is still on good terms with Mark, and OP’s delay makes it feel less like a slip and more like a choice.

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Now OP is stuck between protecting the friendship and ripping off the bandage before Sarah finds out the hard way.

Original Post

I (28M) have been friends with Sarah (26F) for over 5 years. Recently, I opened up to her about struggling to find a meaningful relationship.

She offered to set me up with her ex, Mark (30M), who she's still on good terms with. Initially hesitant, I eventually agreed, and things with Mark quickly became serious.

We've been dating for 2 months now, and Sarah has no idea. I feel guilty for keeping it from her, but my relationship with Mark feels special.

I fear telling Sarah will ruin our friendship, but I also hate lying to her. So AITA for not being honest with Sarah about dating her ex?

The Complicated Nature of Loyalty

This situation digs deep into the complexities of loyalty within friendships. Sarah initially seemed fine with her ex, Mark, dating OP, but that doesn't negate the emotional history they share. The fact that OP has kept the relationship a secret for two months indicates a level of discomfort that speaks volumes.

When do we prioritize friendship over romantic interests? It’s a nuanced question. The OP's internal conflict reflects a broader reality that many face: how much should we consider our friends’ feelings when it comes to pursuing potential relationships? This isn’t just a simple case of dating; it’s a moral quagmire.

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Sarah was totally okay with the idea of Mark dating OP, but the fact that OP waited two months before saying anything is what changes the vibe.

Once OP and Mark went from “maybe” to serious, Sarah’s blessing stopped feeling like a clean pass and started feeling like a trap.

Speaking of friendship fallout, this looks a lot like the Reddit debate over dating Sarah’s ex Mark, and the group-rift it creates.

Why Secrecy Breeds Doubt

The secrecy surrounding OP's relationship with Mark raises critical questions about trust and transparency. While OP might argue that Sarah gave her blessing, the two-month delay in coming clean suggests a serious misalignment in values. If Sarah were to find out, the betrayal could fracture their friendship irreparably.

Additionally, the Reddit community’s response reflects a divide; some sympathize with OP’s dilemma, while others argue that honesty should’ve been the priority from the start. This tension highlights how the fear of hurting someone can sometimes lead to even greater emotional fallout. It makes us wonder: is it ever okay to keep something like this under wraps?

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The guilt is loud because OP isn’t just hiding a relationship, he’s hiding that it grew while Sarah was still acting like Mark was off-limits.

If Sarah finds out after learning she was the last to know, the friendship with Sarah could crack right where it’s been solid for years.

Share your thoughts and experiences in the comments section.

What It Comes Down To

This story showcases the tightrope we often walk between romantic desires and the bonds of friendship. OP's struggle with guilt and secrecy raises a fundamental question about how we navigate our relationships. Should romantic interests ever supersede our friends' feelings? It’s a dilemma that many can relate to, and it invites readers to reflect on their own experiences. What would you do in OP’s shoes? Would you confess or keep the secret to protect your friend?

What It Comes Down To

The situation described highlights the often conflicting nature of friendship and romance. While Sarah initially seemed supportive of her ex, Mark, dating OP, the two months of secrecy suggest that OP's guilt and anxiety about betraying Sarah's trust are weighing heavily on him. This reflects a common struggle—balancing personal desires with loyalty to friends.

If Sarah learns the truth from anyone besides OP, the friendship might not survive the setup.

Worried you’ll blow up your friendship like the AITA case of dating your friend’s ex after they showed interest? Read it here.

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