Should I Reveal My Feelings After Setting Up Best Friends?

Some people don’t realize they are playing matchmaker until the “perfect setup” starts costing them something personal. In this Reddit story, a 29-year-old guy thinks he’s doing a harmless favor for his friends, Sarah and Alex, while quietly carrying a crush he never meant to act on.

It starts with a casual comment, then turns into a carefully arranged meetup. Sarah and Alex hit it off fast, and now they have been dating for weeks, which sounds like a win. But the plot twist is right in the small moments, Sarah confiding how much she likes Alex, while OP is stuck swallowing jealousy and regret every time he hears it.

Now he’s stuck between “I set them up” and “I never told the truth,” and that tension is doing a lot more damage than he expected.

Original Post

So I'm (29M) in a bit of a pickle with my friends, Sarah and Alex. They have been single for a while, and I've always thought they would be perfect together.

One night, we were hanging out, and I casually mentioned to Sarah that Alex had been asking about her. She seemed intrigued and asked if I could set them up.

Without mentioning that I've developed feelings for Sarah over the years, I orchestrated a meetup for them. Sarah and Alex hit it off instantly, and they've been dating for a few weeks now.

Seeing them happy is amazing, but Sarah has started confiding in me about how much she likes Alex. It's becoming increasingly difficult to hide my own feelings.

I never intended for my feelings to get in the way, but now I'm torn. On one hand, I want my friends to be happy, but on the other hand, I can't help feeling jealous and regretful for not being honest about my emotions from the start.

Should I come clean and risk their relationship, or should I continue to support them while battling my own feelings in silence? So WIBTA for setting up my friends and not disclosing my own feelings for one of them?

I honestly don't know if I'm wrong here. Really need outside perspective.

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It’s basically the same mess as the love triangle dilemma over setting up your friend with your crush.

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OP’s plan works immediately, Sarah and Alex click, and suddenly his secret feelings stop being background noise.

Then Sarah starts opening up about Alex, and every sweet conversation feels like OP is being forced to relive the moment he never confessed.

The worst part is that OP did the setup without saying he had feelings for Sarah, so any “honesty” now risks looking like it came with strings attached.

With Alex dating Sarah and OP watching from the sidelines, he has to decide whether to come clean or keep pretending he’s totally fine.

What are your thoughts on this situation? Share your perspective in the comments below.

He might not be the villain, but he’s definitely the reason this friendship could get messy.

Confused like the friend who set up a blind date while hiding his feelings, read this: AITAH for playing Cupid on his crush’s blind date?