Should I Set Up My Friend with My Ex Who Still Likes Me?

A breakup that was supposed to be “amicable” can still leave emotional landmines, especially when your ex is not fully over you. In this Reddit post, a 28-year-old guy just ended a two-year relationship with Sarah, and it sounded peaceful… until he learns Sarah still has feelings for him.

Now he wants to do something nice for his friend Alex, 29, who’s been single and kind of down about it. The plan is a blind date, no big deal, right? Except Sarah’s feelings are already leaking through a mutual friend, meaning the OP knows the setup could light up old chemistry, while Sarah and Alex both have zero clue what’s coming.

The question is not just “should he set them up,” it’s whether he’s about to turn a friendly gesture into a messy love triangle.

Original Post

So I'm (28M) in a bit of a tricky spot. I recently broke up with my girlfriend (25F) of 2 years, let's call her Sarah.

The breakup was amicable, but we both acknowledged that we weren't a perfect match. Enter my friend, let's call him Alex (29M).

He's been single for a while and seems a bit down about not meeting anyone special. So, being the supportive friend I am, I suggested setting him up on a blind date.

Here's where it gets messy. I found out that Sarah still has feelings for me, even after the breakup.

She mentioned this to a mutual friend, who then spilled the beans. I know Alex is a great guy, and I think he would make Sarah happy.

But I can't shake the feeling that I may be crossing a line by setting them up, especially knowing Sarah's lingering feelings. I genuinely want both of them to find happiness, but I'm scared of the potential fallout if things go south.

Should I go ahead with the blind date or would I be the one in the wrong here? For context, Sarah doesn't know about the blind date yet, and Alex is unaware of her feelings for me or that I'm setting them up.

I feel like I'm stuck between helping a friend and potentially hurting another. Hear me out before judging.

So WIBTA?

Why This Setup is a Tightrope Walk

This situation is a classic case of mixing friendship with romantic history. The OP's friend, Alex, is looking for a connection, but the potential setup with Sarah, the OP's ex, adds layers of emotional complexity. The OP knows Sarah still has feelings for him, which complicates the motivation behind the setup. Is it truly for Alex's benefit, or does the OP have a hidden agenda, perhaps seeking validation through Sarah's attention?

Readers are likely divided here because on one hand, helping a friend find love is noble, but on the other, it risks reopening old wounds. There's a real chance that doing this could lead to jealousy and conflict not just between the OP and Sarah but also with Alex if emotions get tangled.

He’s trying to play matchmaker for Alex, but Sarah’s lingering feelings are already sitting in the background like a loaded trap.

Comment from u/RainbowDreamer777

NTA - That sounds like a recipe for disaster. It's noble to want the best for your friend, but involving your ex with lingering feelings is a risky move. Communication is key here.

Comment from u/CoffeeAddict42

YTA - Even with good intentions, setting up an ex and a friend can lead to serious complications. It's best to keep things separate to avoid unnecessary drama. Tread carefully, OP.

Comment from u/jovial_octopus

Honestly, ESH.

Comment from u/PandaPants87

YTA - Mixing exes and friends is always a risky game. You're playing with fire here, OP. It might be best to leave Sarah out of the dating equation altogether to avoid unnecessary heartache for everyone involved.

When the mutual friend spills the secret that Sarah still likes OP, the blind date suddenly stops being “supportive” and starts feeling risky.

Comment from u/MellowMelodies123

I'm gonna say ESH. While your heart may be in the right place, the potential fallout from this setup is enormous. It's a messy situation that could hurt multiple people. Proceed with caution, OP.

It’s like the blind date mess where the best friend has a secret relationship with the mutual friend.

Comment from u/SunshineSkies22

NTA - It's a tough spot to be in, OP. While your intentions are good, the risky nature of this blind date scenario could lead to complicated emotions and strained relationships.

Comment from u/MidnightOwl99

ESH - This is a classic case of good intentions gone wrong. Mixing exes and friends rarely ends well. It might be best to prioritize everyone's emotional well-being and avoid setting up potentially explosive situations. Tread lightly, OP.

OP’s worried about fallout if it goes sideways, because Alex could end up caught in the middle of unresolved ex energy between OP and Sarah.

Comment from u/JazzyCatLady

YTA - It's a bit insensitive to both Sarah and Alex to set them up given the circumstances. Navigating relationships post-breakup is tricky, and adding a friend into the mix only complicates things further. This could potentially backfire, so proceed cautiously.

Comment from u/GamerDude2000

YTA - Mixing an ex with a friend is like playing with emotional dynamite. While your intentions are to help, the fallout from this setup could be messy.

Comment from u/AdventureSeeker44

Proceed with caution and consider all parties' feelings before moving forward, OP.

And the wild part is Sarah doesn’t know about the blind date, while Alex is totally unaware of her connection to OP, so everyone walks in blind.

How would you handle this situation? Let us know in the comments.

The Risk of Playing Matchmaker

This scenario highlights a significant moral grey area. By even considering setting Alex up with Sarah, the OP risks reigniting feelings that both he and Sarah might not be ready to face. It’s one thing to want the best for a friend, but it’s another to play with the emotions of someone who’s still emotionally tied to you.

The community's reaction reveals how personal these situations can feel. Some may empathize with the OP's desire to help Alex, while others might vehemently argue that it’s a betrayal to even think about it. This tension points to a broader truth: love and friendship often collide in messy, unpredictable ways, challenging us to think about who truly deserves our loyalty.

This dilemma raises an intriguing question about boundaries in relationships. How far should one go to help a friend, especially when it involves someone who still has feelings for you? The OP's situation is a reminder that even good intentions can lead to complications. It makes us wonder: can friendships survive when romantic histories are thrown into the mix, or is it too much to navigate without causing harm?

What It Comes Down To

The situation surrounding the OP, Sarah, and Alex reveals the inherent complexities of mixing friendships with romantic pasts. The OP's desire to help Alex find happiness comes from a good place, but knowing that Sarah still has feelings for him complicates the motive behind the setup. This tension reflects a broader truth about relationships: even well-meaning actions can have unintended consequences, as the potential for jealousy and emotional fallout looms large. Ultimately, it's a delicate balance between supporting a friend and respecting the emotional boundaries of an ex.

If this blind date sparks feelings, OP might not just be setting them up, he might be reopening the whole breakup.

Before you set up Alex and Sarah, read why Reddit says it’s wrong to hide their past.