Did I Cross a Line? Setting Up My Friend with My Crush Unknowingly

Some people think setting someone up is harmless, until it quietly turns into a three-person plot twist. This one starts with OP, a 28-year-old guy who’s been best friends with Alex for six years, the kind of friendship where you always show up, no matter what.

Then the feelings get messy. Alex has had a crush on Sarah, a mutual friend, for a long time, and OP has been secretly crushing on Sarah for months too. OP learns Sarah likes Alex, but he keeps his own feelings locked up, then “accidentally” engineers a group hangout so they can spend time together. They hit it off fast, and somehow they plan a date without OP ever finding out.

Now OP is stuck watching two people move forward while he’s wrestling with whether to confess the whole tangled truth.

Original Post

I (28M) have been friends with my buddy, let's call him Alex, for about 6 years now. We've been through thick and thin, always having each other's back, or so I thought.

Little did I know that Alex had a crush on a mutual friend of ours, Sarah, for the longest time. The thing is, I've also been crushing on Sarah secretly for the past few months.

One day, during a casual conversation with Sarah, I found out that she actually likes Alex, but he never made a move. Feeling conflicted, I saw an opportunity to bring them together, so I did.

I organized a group hangout and strategically ensured that Alex and Sarah got to spend some quality time together. They hit it off really well, and before I knew it, they planned a date without my knowledge.

I felt a mix of emotions - happy for them, but also a tinge of jealousy and regret for not revealing my feelings to Sarah earlier. Now, things between Alex, Sarah, and I are a bit awkward.

Alex doesn't know that I also liked Sarah, and Sarah is oblivious to my feelings as well. I'm torn between coming clean about my past crush on Sarah or letting things play out naturally between them.

So, Reddit, with the tangled web I've woven, AITA for indirectly setting up my friend with my crush without their knowledge?

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Also, this feels like the AITA where a matchmaker secretly set up their best friend with their crush, and it blew up fast.

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OP finds out Sarah likes Alex, and instead of backing off, he leans in, scheduling the hangout like it’s a matchmaking mission.

Alex and Sarah start clicking in front of OP, and the date plan happens off-screen, leaving OP to process jealousy in real time.

The awkward part is that Alex has no idea OP also liked Sarah, and Sarah has no clue OP has been quietly steering the situation.

OP has to decide whether to come clean about his past crush or just let Alex and Sarah keep building something he helped kick off.

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

OP may have set up a date, but now he’s the one stuck wondering if he crossed a line.

Still wondering if you should come clean about setting up Alex and Sarah? Check out the AITA where someone set up their best friend with their crush without telling them.