Is It Wrong to Date a Mutual Friends Ex After Discovering a Deep Connection?

A 28-year-old woman is about to find out that love can be messy, especially when it comes with a shared history and a whole friend group watching from the sidelines. She met Alex through their mutual friend Amy, and what started as “just hanging out” turned into real feelings, the kind that do not politely stay in your head.

Here’s the complication: Alex and Amy used to date. They broke up over long-term goals, not because of some dramatic disaster, but because life plans did not match up. Amy is supportive of OP and Alex spending time together, and now Alex is saying the same thing back, he feels it too. But Amy has moved on, and OP is worried a new relationship might still sting, or at minimum, make things awkward for everyone at game night.

The real question is whether a deep connection can survive the math of mutual friends.

Original Post

So I'm (28F) in a bit of a predicament and need some advice. About a year ago, I met this incredible guy (let's call him Alex, 30M) through a mutual friend (Amy, 27F).

Alex and Amy used to date, but they broke up due to differences in their long-term goals. Amy has always been supportive of us hanging out, and I developed strong feelings for Alex.

Recently, Alex confessed that he feels the same way about me, and we realized we have a deep connection that could lead to a serious relationship. Here's where it gets tricky - I'm unsure if pursuing a relationship with Alex would make me the a*****e because of their past relationship.

Amy has moved on and is in a new relationship, but I can't shake the feeling that it might still hurt her or make things awkward among our friend group. Alex and I both believe we have something special and worth exploring, but I don't want to damage my friendship with Amy.

So, Reddit, AITA if I decide to pursue a relationship with Alex despite his history with our mutual friend Amy?

This scenario taps into the complicated nature of friendship dynamics.

Comment from u/catlover1989

Comment from u/gamerchick101

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That warm “we have a deep connection” moment hits fast, right after Amy’s breakup history with Alex is already sitting in the background.

OP keeps thinking about Amy being supportive and also about how supportive people can still get blindsided by new dating news.

Like the OP weighing whether to pursue their friend’s ex after being told “no,”

The Grey Areas of Attraction

The moral grey area here is fascinating. The OP feels a strong attraction to Alex, which complicates her relationship with Amy and challenges conventional friendship norms. Readers might wonder if love should be prioritized over friendship or vice versa. It’s a reflection of a broader societal debate about whether dating a friend’s ex is ever acceptable, especially when feelings seem to develop organically.

This situation also highlights the nuanced reactions from the community. Some readers empathize with the OP’s feelings, while others argue that dating an ex, even with a supportive friend, can lead to hurt feelings and tension down the line.

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Comment from u/randomthoughts22

Meanwhile, Alex and OP both want to explore something serious, even though the friend group could feel the shift the second they start acting like a couple.

And just when everyone is trying to move on, OP has to decide if romance is worth the risk of making Amy’s new relationship feel complicated.

What's your opinion on this situation? Join the conversation!.

The Bigger Picture

This dilemma illustrates the complex web of emotions that intertwine friendships and romantic relationships. It prompts us to ask: is it possible to follow our hearts without stepping on the toes of those we care about? As readers engage with this story, they might reflect on their own experiences and the difficult choices they've faced. What do you think—can love and friendship coexist in harmony when exes are involved?

The Bigger Picture

In this story, the original poster grapples with a classic dilemma of love versus loyalty. Despite Amy's apparent support for her connection with Alex, the OP's uncertainty reflects a deep-seated fear of potential fallout within their friend group. This tension is amplified by the emotional weight of past relationships, as the OP weighs the authenticity of Amy's acceptance against her own desire for a meaningful connection. Ultimately, it’s a relatable struggle that many face: can you truly pursue happiness in love without risking cherished friendships?

If OP chooses Alex, the friend group might not forgive the timing, even if the feelings are real.

See how the OP tried dating their best friend's ex-boyfriend anyway, despite hurt feelings.