Should I Have Told My Friends They Cant Date After I Dated Both of Them?

A 27-year-old guy tried to “protect the group” after dating both of his best friends, and it immediately blew up in his face. Amy and Mark were once his exes, sort of, because the romance fizzled and the friendships survived. But now they want to date each other, and suddenly he feels like he’s stuck playing referee in his own friend circle.

Here’s the mess: Amy (29F) dated him for a couple months, then they stayed close friends. Mark (30M) came next, also a short-lived relationship, also back to being friends. So when Amy and Mark start showing real interest in each other, OP tells them privately to not pursue it, and both reactions land hard, hurt feelings, awkward hangouts, and everyone acting like he’s the villain.

Now the question is whether he was trying to prevent drama or creating it.

Original Post

So I'm (27M) in a bit of a messy situation with my friends (29F) and (30M). About a year ago, I dated Amy (29F) for a couple of months.

It didn't work out, we realized we were better off as friends. That's all cool, we remained close pals.

Then, a few months after that, I started dating Mark (30M). Again, it didn't quite click romantically, but we decided to go back to being friends too.

Now, here's where it gets sticky. Amy and Mark recently expressed interest in each other and want to start a relationship.

Initially, I was supportive, but as time went on, I realized it's making me uncomfortable. I feel like I'm in the middle of their potential romance because of our shared history.

I'm worried it could affect our group dynamic. So, I sat them down individually and told them that I'd prefer if they didn't pursue a relationship.

Both were taken aback and hurt by my request. Amy feels like I'm selfishly standing in the way of her happiness, while Mark thinks it's none of my business who he dates.

Now our group hangs are awkward, and I feel like I've created a rift. So AITA?

I honestly don't know if I'm wrong here.

The Heart of the Matter

This situation highlights a classic dilemma in modern friendships: can you really dictate who your friends can date?

OP was cool with Amy and Mark being friends again, until their “we might date” talk started making the hangouts feel like a minefield.

Comment from u/lucky_ducky99

YTA! You gotta let people live their lives. Your dating history shouldn't dictate their future. Messing with their potential happiness is not cool.

Comment from u/sunset_galaxy23

NTA. It's a complex situation, and your feelings are valid. Maybe instead of telling them not to date outright, sit down together and express your concerns openly. Communication is key.

Comment from u/potato_chip_lover

NAH. It's understandable you feel uncomfortable, but they have the right to explore a relationship. Try to work through your feelings with them and find a way to move forward without damaging the friendship.

Comment from u/coffeesaurus_rex

YTA. You can't control who your friends date, especially after you've dated both of them. Let them make their own choices. This is a messy situation, but you have to step back.

He didn’t just vent, he sat both of them down separately and asked them to stop, which is how you turn a simple preference into a personal attack.

Comment from u/moonbeam_melody

NTA. Your feelings are valid, and it's natural to be uncomfortable. However, your friends should also understand your perspective.

This messy Amy and Mark triangle echoes the AITA where someone struggled to support a friend dating a mutual friend.

Comment from u/sleepy_penguin87

Just gotta say, that's a whole lot of drama for one friend group. Y'all need to sit down, communicate, and figure this out together. It's messy, but avoiding the issue will only make it worse.

Comment from u/sparkleunicorn88

ESH.

Amy took it as selfish interference, while Mark called it his business who he dates, and that mismatch is exactly why the group dinner energy went stale.

Comment from u/bananarama_drama

YTA. While your discomfort is understandable, you can't control their lives. It's better to address your feelings openly and work towards a resolution that respects everyone's autonomy. This situation needs mature handling.

Comment from u/jazzyjellybean22

NTA. It's a sticky situation, but your feelings are valid. Relationships within a friend group can be complicated. However, ultimately, they have the right to explore their connection. Communication is key here.

Comment from u/tacotuesday_forever

Honestly, this is a whole soap opera waiting to unfold. It's not cool to try and control who dates who, but considering your dating history, I get the discomfort. Best thing is open communication. Good luck, OP!

Even though OP meant to avoid a rift, the second he drew a line between Amy and Mark’s dating plans, the friend group became the battleground.

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

Why Boundaries Matter

The OP's declaration that Amy and Mark shouldn't date is a bold move, and it reflects an internal struggle with jealousy and possessiveness. Friends often find themselves in these sticky situations where past relationships can cast shadows over new ones. The OP’s worry about how their friendship might change if Amy and Mark start dating is a real concern, especially since it’s often tough to balance loyalty with personal feelings.

This is where the community reaction gets interesting. Some commenters argue that the OP's feelings are valid and that they should express their discomfort, while others see it as an overreach.

The Bottom Line

This story encapsulates the intricate dance between friendship and romance, reminding us that relationships can be a tangled web of emotions. The OP's struggle to navigate their feelings about Amy and Mark dating is one many can relate to, which is why this topic sparks such heated discussions. It raises the question: how do you maintain friendships when past relationships complicate things? Where do you draw the line between support and self-preservation?

The Bigger Picture

The situation with Amy and Mark highlights a classic struggle of navigating friendship boundaries after romantic entanglements.

Nobody wants to feel like they’re dating around OP’s old mistakes.

Want to see how someone handled banning a friend from dating their ex? Check out the AITA where a guy set a rule against his friend dating his ex.