Is It Wrong to Date My Friends Ex Despite Her Unspoken Disapproval?

"Is it wrong to date my friend's ex if she hasn't expressed disapproval? Reddit users weigh in on navigating unspoken tensions and potential friendship fallout."

A 29-year-old woman is about to find out that dating someone connected to your best friend can feel like walking on glass. She and Lily have been close for years, the kind of friendship where you know each other’s patterns, moods, and history without even trying.

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Lily dated Ryan for almost three years in college, then they broke up because of distance, and Lily was genuinely heartbroken. About a year later, the OP developed feelings for Ryan, but she pulled back out of respect. Now, at a mutual friend’s party, Ryan and the OP hit it off hard, he confessed feelings too, and things are getting real, even though Lily has never said a word about it.

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The tension is there, unspoken, and the OP is terrified that one happy “maybe” could turn into a friendship disaster.

Original Post

I (29F) have been friends with Lily (28F) for years, and we've always been super close. Throughout college, Lily dated Ryan (30M) for almost three years.

Unfortunately, they broke up due to distance, and Lily was heartbroken. About a year after their breakup, I unexpectedly developed feelings for Ryan.

However, knowing Lily's history with him, I kept my distance. Fast forward to now, Ryan and I bumped into each other at a mutual friend's party and hit it off.

He confessed that he had feelings for me too. We both felt a strong connection.

We haven't officially started dating but have been talking a lot and spending time together. Here's the dilemma: Lily has never explicitly discussed Ryan post-breakup, but I can sense some tension whenever he's mentioned.

She never brought up any lingering feelings for him or told me explicitly not to date him. But I can't shake the feeling that she might be hurt if she finds out.

So, would I be the a*****e for pursuing a relationship with Ryan, knowing it might upset Lily even if she hasn't communicated her feelings about him? I care about both of them deeply, and I don't want to lose my friendship with Lily over this potential relationship.

So, WIBTA?

Treading on Thin Ice

This situation dives deep into the complexities of friendship and romantic relationships. The OP's feelings for Ryan, her friend Lily's ex, highlight a common yet complicated dilemma. What happens if Lily finds out? The fear of betrayal is palpable, and it’s this unspoken disapproval that makes the potential fallout so dangerous.

When friendships are built on trust and loyalty, dating an ex can shatter that foundation. It's not just about seeking happiness; it's about navigating the emotional minefield that could lead to a friendship breakdown.

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Comment from u/RandomAdventure47
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Comment from u/TigerTeaParty_99

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The OP has been quietly avoiding Ryan for months, even while Lily’s breakup with him still hangs over every mention of his name.

The Community Divide

The Reddit thread sparked a lively debate, revealing how divided people can be on issues of loyalty and love. Some users argued that feelings are natural and should be pursued, while others emphasized the importance of considering Lily's feelings, even if they're unvoiced. This tension reflects a larger societal question: how much weight should we give to unspoken disapproval? It's fascinating how this situation mirrors many real-life scenarios where friends find themselves at odds over romantic interests, showcasing the fragility of relationships.

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Comment from u/SunnySideUp11

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Comment from u/WhisperingWillow_22

Comment from u/WhisperingWillow_22

Then at that mutual friend’s party, Ryan and the OP went from awkward bump-in to full-on chemistry, and Lily’s “silent tension” suddenly feels louder.

It’s like the Reddit user who gave dating advice, then caught feelings for the friend they were advising in the friend zone.

Friendship vs. Romance

The OP’s dilemma raises important questions about the hierarchy of relationships. Is a longstanding friendship with Lily worth risking for a potential romance with Ryan? The dynamic becomes even more complex when considering how often friendships are tested by romantic connections. The pressure to choose sides can be overwhelming and often leads to resentment.

This situation reflects a common pattern where individuals feel torn between their desires and loyalty. It’s a moral gray area that invites readers to reflect on their own experiences and the sometimes rigid rules that govern friendship and love.

Comment from u/MidnightMuse77

Comment from u/MidnightMuse77

Comment from u/RainbowRider123

Comment from u/RainbowRider123

Comment from u/SunnySunflower28

Comment from u/SunnySunflower28

The most brutal part is that Lily never explicitly told her to stop, but the OP can still sense something is off whenever Ryan comes up.

Unspoken Feelings Matter

One of the most striking elements here is the weight of unspoken feelings. Lily hasn’t voiced her disapproval, but that doesn’t mean she’s okay with the situation. This silence can often speak volumes and creates a heavy atmosphere of uncertainty. It puts the OP in a precarious position where she must navigate her own feelings while being mindful of the invisible boundaries that friendship creates.

While some might argue that love should prevail, the emotional stakes are high. If Lily feels hurt, it could lead to a fracture that might not heal. This precarious balance between pursuing personal happiness and maintaining friendship loyalty is a tough lesson for many.

Comment from u/CoffeeCraze_87

Comment from u/CoffeeCraze_87

Now the OP has to decide if she’s about to protect her friendship with Lily or risk it all for a relationship with Ryan that neither of them has fully admitted out loud yet.

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

Where Things Stand

In the end, this story underscores the complexities of human relationships, where love, friendship, and unspoken feelings intertwine in unpredictable ways. As the OP contemplates her next move, it raises a vital question: is it ever truly worth pursuing a romantic relationship at the potential cost of a cherished friendship? How do you navigate these tricky waters without losing what matters most?

The situation with the 29-year-old woman, her friend Lily, and Lily's ex Ryan reveals a classic conflict between personal desire and loyalty. Despite Ryan and the poster hitting it off, the lingering tension surrounding Lily’s unvoiced feelings casts a shadow over their potential relationship. This hesitation hints at a deeper concern about respect and the unspoken rules that often govern friendships, especially when past romantic ties are involved. Ultimately, the poster's dilemma illustrates how navigating these emotional waters can lead to significant anxiety about the fallout with a close friend.

If Lily finds out the OP and Ryan are becoming a real thing, that friendship might not survive the fallout.

Still stuck between love and loyalty, read about dating your best friend’s ex and the emotional turmoil it sparks.

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