Caught Between Friends: Should I Set Up My Crush with My Friend When I Have Feelings for Her?

A 28-year-old woman refused to play matchmaker for the man her friend is crushing on, and the fallout was way messier than she expected. It started as a “casual group hangout” plan, the kind where everyone laughs, drinks something, and pretends romance is optional.

OP has been friends with Lily for years, and Lily knows OP has had a crush on Ben from the same friend group for a while. Then Lily asks OP to set her up with Ben, OP says yes, and the second Lily and Ben click, OP’s feelings flip into something sharper and more confusing. To make it worse, Lily later admits she’s starting to develop feelings for Ben too.

Now OP is stuck, wondering if backing out will protect her friendship, or blow it up completely.

Original Post

So I'm (28F) and I’ve been friends with Lily (26F) for years. We always share our dating stories, and she knows that I've had a crush on Ben (30M) from our friend group for a while now.

Lily recently mentioned that she finds Ben attractive and asked if I could set them up. I agreed, thinking I could help them both find happiness.

I organized a casual group hangout where Lily and Ben hit it off instantly. Seeing them connect sparked unexpected feelings in me; I realized I might have deeper emotions for Lily than just friendship.

I felt torn, trying to be happy for them while struggling with my own newfound realization. Lily later confided in me, mentioning that she's starting to develop feelings for Ben.

My heart sank as I listened, grappling with a mix of emotions. On one hand, I want Lily to be happy, but on the other, I can't shake off these feelings I have for her.

I haven't told Lily about my change of heart regarding Ben or my feelings for her. It's complicated, and I fear I might jeopardize our friendship.

Would I be the a*****e if I backed out of setting them up and confronted my own emotions instead? So, WIBTA if I refuse to set up my friend with my crush, only to realize I have feelings for my friend?

I honestly don't know what to do here.

The Heart of the Dilemma

This situation speaks to the messy intersection of friendship and romantic feelings. The OP's initial desire to help her friend Lily pursue Ben highlights her selflessness, but it also sets up a classic love triangle that complicates everything. When feelings for Ben unexpectedly blossom, it forces her to confront not just her emotions but also her loyalty to Lily.

The irony here is palpable: she wanted to play the role of a supportive friend, yet she finds herself at the center of a potential heartbreak for both herself and Lily. Readers can relate to this tension, as many have faced similar crossroads where friendship and desire collide in unpredictable ways.

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OP agreed to set up Lily and Ben, even though she already had a crush on Ben herself, which is where the emotional trapdoor starts.

Community Reactions: Divided Opinions

The Reddit community's reactions to this post reveal a fascinating divide. Some users suggest the OP should come clean to Lily, arguing that honesty is the best policy, while others caution against complicating the friendship further. This conflict over how to handle such a delicate situation showcases differing values around loyalty, transparency, and romantic pursuit.

Many commenters also empathize with the OP's struggle, with some sharing their own stories of unrequited love within friend groups. This kind of resonance underscores how common these emotional entanglements are, revealing a collective understanding of the awkwardness that often accompanies navigating feelings in social circles.

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The group hangout goes fine, Lily and Ben hit it off instantly, and OP realizes her “helping” mission just lit her own feelings on fire.

It’s also like the dilemma in “Should I Tell My Friend I Cant Set Them Up With My Crush?”, where loyalty collided with feelings when someone refused to play matchmaker.

The Fear of Losing Both

What’s particularly poignant here is the OP’s fear of losing both her friend and her crush. On one hand, she wants to support Lily, but on the other, she can't ignore her own feelings. This duality creates a moral grey area that makes the situation even more complex. If she tells Lily, will that ruin their friendship? But if she keeps quiet, will she miss out on a potential relationship with Ben?

This dilemma encapsulates a common fear in friendships: can you truly have it all? The stakes feel especially high when the potential for loss is so real, making this not just an emotional conflict, but a test of the strength of their bonds.

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Then Lily confides that she’s catching feelings for Ben, and OP has to sit there with a sinking heart and a secret.

This story also dives into the complex nature of jealousy and support in friendships. The OP’s original intention to be a supportive friend to Lily by playing matchmaker gets turned on its head once her feelings for Ben surface. This kind of emotional whiplash is something many readers can relate to, as jealousy often lurks beneath the surface in relationships.

It raises the question of whether it’s possible to genuinely support a friend while grappling with romantic feelings for the same person.

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So when OP considers refusing to set them up and confronting her feelings for Lily, it turns every friendship move into a potential heartbreak headline.

What would you do in this situation? Share your opinion in the comments.

Where Things Stand

This emotional labyrinth illustrates how easily intentions can shift when love enters the equation. The OP's journey from matchmaker to conflicted friend resonates because it taps into a common fear of losing what we cherish most. Readers are left wondering: how do we navigate the tricky waters of friendship when our hearts have other plans? Would you prioritize honesty with a friend, or protect your feelings instead?

Why This Matters

The situation faced by the 28-year-old woman highlights the complexities of friendship and romantic feelings.

Nobody wants to be the reason Lily and Ben get close, and nobody wants to lose Lily when those feelings finally show up.

Before you confess to Lily, read how one friend’s setup with a crush backfired in “Conflicted: Setting Up Friend with Crush Leads to Unexpected Feelings.”