Should I Have Dated My Best Friends Ex? AITA?

A 28-year-old woman refused to ignore the spark that started growing the moment her best friend’s breakup left a very convenient opening. Emily and Mark had been together for years, and Mark was basically part of the friend group, the kind of guy everyone knows and trusts.

After Emily and Mark split, OP started spending more time with Mark to help him cope, and it didn’t stay strictly “comforting a friend.” A little closeness turned into real feelings, and soon OP and Mark were officially dating, even if they tried to keep it quiet at first.

But when Emily found out, it wasn’t just awkward, it was devastating, and now OP is stuck choosing between a relationship she wants and a friendship she can’t bear to lose.

Original Post

So I'm (28F), and I've been friends with Emily (27F) since college. We've always been super close, sharing everything from clothes to deepest secrets.

Around six months ago, Emily broke up with her longtime boyfriend, Mark (30M). They were together for years, and he was like a part of our friend group.

After the breakup, I started spending more time with Mark to help him cope. We'd always gotten along well.

One thing led to another, and we realized there was a spark between us. We both felt guilty but couldn't deny our feelings.

We decided to give it a shot. Fast forward to now, and Mark and I are officially dating.

We tried to keep it under wraps initially, but someone spilled the beans, and it got back to Emily. She was devastated and felt betrayed by both of us.

She texted me, saying she can't believe I'd date her ex and that it's like a double betrayal since I was one of her closest friends. Emily wants me to end things with Mark to salvage our friendship, but I care about him deeply.

He's been understanding of the situation and is torn between our relationship and his friendship with Emily. I feel stuck in the middle.

Emily is hurt, Mark is torn, and I'm torn. I never intended to hurt Emily, but I can't deny my feelings for Mark.

So AITA?

The Loyalty Dilemma

This situation really highlights the tension between romantic feelings and loyalty to friends. The OP's choice to date Mark, Emily's ex, is a classic case of crossing relational boundaries. Even if the breakup was amicable, the emotional aftermath for Emily isn’t something to gloss over. It’s easy to see why Emily might feel betrayed, as dating an ex is often perceived as a betrayal of trust, even if Mark and the OP believe their connection is genuine.

What complicates this further is the timing; jumping into a relationship with someone who's just out of a serious relationship is fraught with emotional baggage. Readers can feel the rift forming, and it’s no wonder the community is divided. Some sympathize with the OP's pursuit of happiness, while others staunchly defend the unspoken rules of friendship.

That first “help him cope” phase with Mark is where everything starts getting messy for OP, because Emily watched it happen in real time.

Comment from u/MusicLover_88

YTA. Your friendship with Emily should have come before any romantic feelings for her ex. She's right to feel hurt and betrayed.

Comment from u/SunnySideUp23

NAH. Relationships are complicated. It's unfortunate that it's caused a rift, but feelings are genuine. Have an honest conversation with Emily and Mark.

Comment from u/AdventureSeeker42

NTA. Love is unpredictable. You didn't set out to hurt Emily intentionally. Sometimes relationships shift, and it's a tough situation for everyone involved.

Comment from u/PizzaIsLife

YTA. Dating your best friend's ex crosses a major friendship boundary. Consider how you'd feel if the roles were reversed.

When the spark between OP and Mark turned into an actual relationship, Emily didn’t just feel jealous, she felt blindsided.

Comment from u/CoffeeAndBooks

ESH. Emily may feel betrayed, but Mark was also part of the decision.

It’s also like the AITA love triangle where a friend objected, but feelings won anyway.

Comment from u/SoccerMom99

NAH. It's a tough spot for everyone. Just communicate openly and honestly with both parties. Your feelings are valid, but so are Emily's.

Comment from u/TechWizard123

NTA. Sometimes unexpected connections happen. It's essential to prioritize your own happiness, but try to mend things with Emily if possible.

The fact that “someone spilled the beans” makes it worse, because Emily’s betrayal meter probably hit max the second the news reached her.

Comment from u/BeachBum4Life

NAH. Love is complex, but friendships are crucial too. Navigate this situation with empathy and understanding for all parties involved.

Comment from u/CatLoverForever

YTA. Dating a friend's ex is a sensitive issue and can deeply hurt the friend. Consider the impact on Emily's feelings and your friendship.

Comment from u/GamerGirl3000

NAH. Emotions are messy, and sometimes unexpected connections form.

Now Emily is demanding OP end things with Mark to “salvage our friendship,” while Mark is stuck torn between his new relationship and his long-time bond with Emily.

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

The emotional fallout from this scenario is palpable. It’s not just about the romantic connection; it’s the ripple effect on friendships that makes it so relatable and contentious. Readers are drawn into the drama because it reflects a common dilemma: how do we balance personal desires with loyalty to friends? The OP may see her relationship with Mark as a fresh start, but for Emily, it’s a painful reminder of what she lost.

This is where the Reddit community really shines, offering a mix of support and tough love. Many are quick to point out that while love can be unpredictable, there are still unspoken codes that should be respected, especially among friends. The debate over whether the OP's actions were justified or selfish adds layers to an already complicated situation, making it a topic that sparks heated discussions.

Why This Story Matters

This story underscores the complex dynamics at play when love and friendship collide.

Why This Matters

In this unfolding drama, the Redditor's decision to date Mark, her best friend's ex, reveals the tension between personal desires and loyalty. The closeness of her relationship with Emily makes the betrayal feel even more pronounced, as Emily's heartbreak over the breakup is compounded by the perceived disloyalty of a friend. This situation illustrates how quickly emotions can escalate when romantic feelings intersect with established friendships, leaving everyone involved feeling vulnerable and conflicted. The community's divided opinions reflect the complexity of these relational boundaries, making it a relatable conflict for many.

OP might not be the villain, but she’s definitely the person who broke the friend group in half.

For more fallout after your best friend said “yes,” read the AITA where dating your best friend’s ex turned into instant regret.