Should I Play Cupid for My Friend and Crush, Risking Our Friendship?

Sometimes love shows up dressed like a “harmless” favor, and that is exactly what happened in this messy little love triangle. OP is best friends with Tom, the kind of friendship where secrets get traded like souvenirs, and hanging out is just their default setting.

Then Tom drops a confession, he has feelings for Sarah, a mutual friend. Meanwhile, OP admits he has been low-key crushing on Sarah for a while too, which means his matchmaker move is not exactly neutral. OP sets them up on a date, hoping it works out for Tom, but he cannot shake the fear that he is gambling with his bromance, and possibly with Sarah’s feelings, just to get a shot at the same girl.

Now OP is stuck wondering if he played Cupid for the right reasons, or if he just set his friendship on fire.

Original Post

So, I'm a 27-year-old guy, and I've been friends with my buddy, let's call him Tom, for the longest time. We've always been close, sharing secrets, hanging out, you know the deal.

Well, the plot thickened when Tom confessed to me that he has feelings for our mutual friend, Sarah. Here's the kicker: I've been low-key crushing on Sarah for a while.

I spent late nights thinking about her, but I never made a move. Now, Tom comes to me for advice on how to woo Sarah.

Hear me out. In a sudden bold move, I decide to play matchmaker and set Sarah and Tom up on a date, hoping for them to hit it off.

But there's a gut feeling gnawing at me, wondering if this move might ruin our bromance. I might be jeopardizing my friendship with Tom for a shot at Sarah.

Am I being a total jerk for playing with their hearts, including mine? So, WIBTA?

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Also, this is like the debate in dating a friend after a confession, risking the friendship.

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Tom’s confession to OP about Sarah is the moment everything goes from “normal friends” to “oh no, this could get complicated fast.”

OP’s secret crush on Sarah turns the whole “help Tom woo her” plan into something way more personal than he’s admitting.

The date gets set up anyway, and now OP is waiting to see if Sarah and Tom hit it off or if his bromance takes the hit.

With OP already feeling guilty about risking their bromance, the real question becomes whether he can live with the fallout if it doesn’t work out.

What do you think about this situation? Let us know in the comments.

OP might have wanted to help Tom win Sarah, but he could end up losing Tom instead.

For another love-triangle mess, read whether you would set up Tom with Sarah.