Dating Best Friends Ex: A Dilemma of Love and Loyalty

A 27-year-old guy is stuck in the kind of romantic tangle that sounds simple until it hits you in the chest. He and his best friend Alex have been inseparable since they were kids, the kind of bond that survives everything, including heartbreak.

Then Alex dated Sarah about a year ago. It ended on decent terms, they stayed friends, and now Sarah and the OP are catching feelings for each other. The problem is brutal, he hasn’t told Alex because he doesn’t want to hurt him, and Sarah is worried she’ll somehow come between two people who have always had each other.

So now it’s love versus loyalty, and the entire friend group might feel the fallout.

Original Post

I (27M) have been best friends with Alex (28M) since we were kids. We've always had each other's backs through everything.

About a year ago, Alex dated Sarah (26F) for a few months, but they broke up on good terms and decided they were better as friends. Since then, Sarah and I have gotten to know each other more, and we've developed feelings for each other.

We both believe we could have something special. Here's the dilemma: I'm conflicted about pursuing anything with Sarah because of my loyalty to Alex.

I value our friendship immensely, but I can't deny the connection I feel with Sarah. I haven't mentioned my feelings to Alex yet because I know it might hurt him.

Alex hasn't shown any interest in rekindling things with Sarah, but I can't shake off the guilt of potentially betraying him. Sarah is also torn because she doesn't want to come between us.

I don't want to lose my friendship with Alex, but I also don't want to miss out on a possible great relationship with Sarah. It's a tough decision, and I'm really torn.

So, Reddit, AITA for considering dating my best friend's ex?

The Loyalty Tension

This situation is a classic example of the loyalty versus love dilemma. The OP's long-standing friendship with Alex complicates his feelings for Sarah, who’s still tied to his best friend in emotional memory. While some might argue that love should take precedence, the fallout from dating a friend's ex can be devastating.

There's a real risk of damaging the friendship if Alex feels betrayed. The emotional stakes are high here, especially since the friendship has weathered time. It's a precarious balance, and the OP needs to consider how much he values that bond against the potential for a romantic relationship with Sarah.

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The OP is trying to keep things calm with Alex, even though Sarah is getting closer and the “just friends” line is starting to blur.

The Community Divide

This Reddit thread ignited a fierce debate, with responses clearly split down the middle. Some users staunchly defended the OP's right to pursue what feels right in his heart, while others felt the emotional fallout for Alex was simply too grave. This division highlights how deeply personal relationships can provoke strong and varied opinions.

People tend to project their own experiences onto situations like this. For some, dating a friend's ex is a cardinal sin; for others, it's just a part of navigating adult relationships. The community's responses reveal how experiences shape our views on loyalty, love, and friendship.

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After realizing Alex has no interest in Sarah, the OP still feels guilty, like dating her would be a betrayal he can’t undo.

It’s the same loyalty versus love squeeze as a friend confessing feelings and then questioning whether dating their ex is WIBTA.

The Complicated Nature of Exes

Dating a friend's ex isn't just about the two people involved; it’s about the entire social dynamic. Sarah's past with Alex complicates her potential relationship with the OP. Even if Alex has moved on, the emotional residue of their relationship might linger, affecting how he views any new developments.

This situation raises questions about how much we owe our friends when it comes to love. Is it fair to put a romantic connection above a friendship that’s been built over years? Each choice carries potential consequences, and that’s what makes the OP’s decision so weighty.

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Meanwhile Sarah is caught in the same crossfire, she likes the OP, but she doesn’t want to be the reason their friendship cracks.

The grey areas in this story make it so compelling.

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Then the Reddit comments kick in, and the thread turns into a full-on loyalty vs love debate over whether the OP should risk it with Sarah.

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

The Bottom Line

This story resonates because it taps into a universal conflict many face: the tension between love and loyalty. It forces us to consider how far we’re willing to go for our romantic desires at the expense of friendships. As readers, we can’t help but wonder what we would do in the OP’s shoes. Would we prioritize our own happiness or protect a cherished friendship?

The Bigger Picture

In this story, the young man’s internal struggle highlights the complexities of love and loyalty. His long-standing friendship with Alex creates a strong emotional barrier against pursuing a relationship with Sarah, despite their mutual feelings. This dilemma is further complicated by the amicable nature of Alex and Sarah's breakup, leaving the protagonist feeling guilty about potentially jeopardizing a friendship that has been built over years. It’s a classic case of weighing personal happiness against the bonds of friendship, a challenge that many can relate to.

He might get the relationship he wants, but it could cost him the friendship he’s been protecting his whole life.

Still torn about dating your best friend Alex’s ex Sarah, check this out: friend-ex loyalty clash. Is it Okay to Date a Friends Ex? Navigating Feelings for a Mutual Friend.