Should I Talk to My Friend About Dating My Crush? | Relationship Advice

Some people don’t recognize a boundary, even when it’s been quietly sitting in the open for years. In this story, a man watches his close friend get cozy with the exact guy he’s been carrying a crush for, and it’s turning “maybe someday” into a real emotional gut punch.

OP, 27M, has been close with Lily, 25F, for years, and he already told her he liked their mutual friend Alex, 29M. Then Alex and Lily start spending more time together, showing up like they’re on dates, and OP feels betrayed, even though both are single. Now he’s stuck between wanting to say something and worrying that telling Lily how much it would hurt him might come off controlling.

Original Post

So I'm (27M) and have this close friend, let's call her Lily (25F). We've been friends for years, and she knows I've had a crush on our mutual friend, Alex (29M), for quite some time now.

In fact, I confided in Lily about my feelings for Alex a while back. Well, recently, I noticed some chemistry between Alex and Lily, and it's been making me feel really uncomfortable.

They've been spending a lot of time together, going out on what seem like dates, and it's starting to eat at me. For background, Alex and I have had this unspoken connection, and I thought maybe there could be something more between us someday.

But now that I see him getting closer to Lily, I can't help but feel betrayed. I know they're both single and can be with whoever they want, but it just hurts seeing them together, knowing how I feel.

I've been thinking about talking to Lily and expressing how I feel about the situation. I want to let her know that her dating Alex would really hurt me, especially since she's aware of my crush on him.

But I'm torn because I don't want to come off as controlling or ruin their potential relationship if they really like each other. So WIBTA for confronting Lily about this, even though she knows how I feel about Alex?

This scenario places the OP in a classic love triangle, but the emotional stakes are even higher given the close friendship with Lily. Confiding feelings for Alex to Lily creates a layer of expectation that complicates things further. It’s not just about wanting to date someone; it’s also about feeling betrayed by a close friend who, in this case, seems to have disregarded the OP’s feelings.

Most people can relate to the feeling of jealousy when a close friend gets involved with someone they like. The OP's struggle to confront Lily speaks to the broader theme of loyalty versus desire, making it a situation many have faced at least once in their lives.

Comment from u/coffeelover98

Comment from u/starrynight_123

Comment from u/gamer_gal17

OP already confessed his crush to Lily, so when Alex and Lily start acting like a couple, that old confession suddenly feels like a loaded gun.

The Complicated Nature of Confessions

This Reddit post sparks debate because it illustrates the messy fallout of sharing personal feelings. Once the OP confided in Lily, the expectation was set that she would be sensitive to his feelings. Yet, seeing her grow closer to Alex could understandably feel like a betrayal.

The contradiction here is palpable: should Lily have been more considerate of the OP's feelings, or is it her right to pursue her own happiness? This moral grey area is what resonates with readers, as many have been caught between friendship and romantic interest.

Comment from u/wanderlust_dreamer

Comment from u/potatochipaddict

Comment from u/moonchild33

The worst part is Lily knows the history, yet OP keeps noticing more “date” vibes between her and Alex, and it’s messing with his head.

This feels like the AITA fight where someone refused to introduce their friend to their crush after learning the crush was suddenly interested in them.

See the full AITA story.

Community Reactions: Divided Opinions

The responses to this thread are telling.

Comment from u/beachlover_89

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Comment from u/gardengal456

That’s when OP starts thinking about confronting Lily, but he’s scared of sounding like he’s policing her choices instead of sharing his feelings.

The Risk of Vulnerability

At the heart of this dilemma is the risk that comes with vulnerability. By opening up about his feelings for Alex, the OP took a significant emotional leap. However, watching those feelings potentially slip away to a friend can feel like a betrayal of that vulnerability.

This situation emphasizes that while sharing feelings can lead to stronger connections, it can also lead to hurt and disappointment. The OP's decision on whether or not to confront Lily will ultimately shape not just his relationship with her, but also his own emotional health moving forward.

Comment from u/musiclover22

With Alex and Lily continuing to spend time together, OP has to decide whether the truth helps him, or just blows up the friendship faster.

We'd love to hear your take on this situation. Share your thoughts below.

This story highlights the intricate dance between friendship and romantic feelings, as well as the emotional stakes involved when those lines blur. It raises the question: how do we balance our own desires with the feelings of those we care about? Readers may find themselves reflecting on their own experiences in similar situations. What would you do if you were in the OP's shoes? Would you confront your friend, or would you prioritize your friendship over your feelings?

The Bigger Picture

In this scenario, the 27-year-old man finds himself in a painful predicament as he watches his close friend Lily grow closer to Alex, the object of his affection. Having confided in Lily about his crush, it’s natural for him to feel a sense of betrayal when he sees them together, as it complicates the emotional landscape of their friendship. The internal conflict he faces—whether to express his discomfort or protect their potential happiness—highlights the delicate balance between loyalty and the pursuit of personal desires, something many can relate to in similar situations. Ultimately, his struggle reflects a common human experience: the challenge of navigating complex emotions when love and friendship intersect.

He’s not just jealous, he’s about to find out whether honesty with Lily will save the friendship or ruin it.

Before you spill it to Lily, check out what happened when someone confronted their friend about flirting with their mutual crush. Read the WIBTA debate.