Should I Tell My Friend About Her Crush Before Setting Her Up on a Blind Date?

A 28-year-old man tried to do a sweet birthday favor for his friend, Amy, and immediately stepped onto a moral landmine. He knows she’s been hinting at having feelings for him, but he also knows she’s tired of being single, so he decides to play matchmaker anyway.

His plan is simple: call up Mark, a nice guy looking to date, set up a blind date for Amy’s birthday, and let them “hit it off” without ruining the surprise. The complication? When Amy learns about the blind date, she’s excited, then keeps dropping hints that she wishes it was with him, and now guilt is creeping in fast.

It’s the kind of setup where one birthday dinner could either help Amy move on, or blow up the friendship.

Original Post

So, I (28M) have this friend, let's call her Amy. We've been friends for a few years, and recently, she's been dropping hints about having feelings for me.

But here's the thing - I don't feel the same way. Last week, Amy mentioned how she's tired of being single and wants to meet someone great.

Her birthday is coming up, so I thought I'd do something nice for her. I know this guy, Mark, who's really sweet and looking to date.

I figured they might hit it off. I called Mark and arranged a blind date for him and Amy on her birthday.

I didn't mention that she has a crush on me. I thought it would be a nice surprise for her and a chance for her to move on.

When I told Amy about the blind date, she got really excited but kept dropping hints that she wished it was with me. Now I'm starting to feel guilty.

Should I have told her about her crush on me before setting her up? Would I be the a*****e if I went through with the blind date without saying anything?

The Moral Tightrope

This whole situation really underscores the moral tightrope the OP is walking. They want to help their friend Amy, but by setting her up on a blind date without revealing her crush on them, they risk straining their friendship.

It’s a common dilemma: how do you prioritize friendship while also respecting romantic feelings?

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That “nice surprise” idea gets messy the second Amy hears about Mark and still keeps steering the conversation back to OP like she wants him to notice her first.

Friendship vs. Romance

What really gets people talking in this story is the conflict between friendship and romantic feelings. The OP is in a tough spot, trying to set Amy up for a chance at love while knowing she’s got a crush on them. This contradiction is relatable for so many; it’s not uncommon to have friends who develop feelings that complicate the dynamics.

Readers can feel the tension between wanting to help a friend and the fear of making things worse. It raises the question: should the OP be upfront about Amy’s feelings before making any moves? The ambiguity is what makes this situation resonate with readers.

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OP’s birthday plan, Mark and all, turns into an awkward guessing game once Amy’s hints make it clear she’s not actually trying to forget him.

It’s the same kind of mess as the Reddit debate over secret blind dates when friends have crushes.

Should I Tell My Friends Their Blind Date Crushes? | Reddit Dilemma

Community Reactions

The Reddit community’s reaction to this dilemma is telling.

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The guilt ramps up because OP basically built a detour for Amy, even though her heart seems parked on him, not on Mark.

Complications of Modern Dating

This story encapsulates the complications of modern dating, especially when friendships are involved. The OP’s desire to help Amy move on is commendable, but it can also feel like they’re playing matchmaker with a loaded gun. There’s an inherent risk in trying to navigate feelings that haven’t been fully addressed.

As the dating landscape becomes more complex, situations like this remind us that emotional transparency is often lacking. It’s easy to see how the OP might think they’re doing the right thing, but without engaging in an open conversation, they could inadvertently push Amy further into confusion or heartbreak.

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And if OP goes through with the blind date anyway, Amy might leave with new hope for Mark, or worse, a fresh reason to feel rejected by OP.

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

Why This Story Matters

This intricate web of friendship and unspoken feelings highlights how complicated romantic entanglements can be. The OP’s intentions are rooted in caring, yet they risk misstepping by not addressing Amy’s feelings head-on. It begs the question: how do you balance helping a friend with being honest about emotions? Have you ever faced a similar situation where friendship and romance clashed?

In this scenario, the user’s actions reflect a genuine desire to help their friend Amy find happiness, but they’re also navigating a minefield of unspoken feelings. By arranging a blind date with Mark, they aim to facilitate Amy’s move on from her crush, yet this well-meaning gesture could lead to confusion since Amy's hints reveal she still harbors feelings for the user. The tension stems from the classic dilemma of wanting to support a friend while also acknowledging the complexities of romantic emotions, which can easily put friendships at risk if not handled with transparency.

He might be trying to help Amy find love, but right now he’s risking being the person who makes it hurt.

Before you set Amy up with Mark, see what happened when someone knew the friend loved them.

Should I Set My Friend Up on a Date While Knowing He Loves Me?