Should I Set Up My Best Friend with My Crush?

Some friendships survive awkward secrets, but this one is getting shredded in real time. A 28-year-old guy is watching his best friend and his crush orbit the same person, and the worst part is he’s the one being asked to play matchmaker.

Here’s the mess: OP has had a crush on Sarah since forever, and Alex, his best friend since college, always knew it. Then Sarah and OP started getting closer, and he was ready to ask her out. Right when it feels like things might finally go his way, Alex drops the bomb that he also has feelings for Sarah, and he wants OP to help set them up anyway.

Now OP is stuck between loyalty to Alex, fear of losing Sarah, and the sinking feeling that he’s about to get hurt for a relationship he wanted first.

Original Post

So, I'm (28M) in a complicated situation with my best friend Alex (27M) and my crush Sarah (26F). Alex and I have been friends since college, and he has always known that I had a crush on Sarah.

Recently, Sarah and I started getting closer, and I was planning to ask her out. However, Alex confessed to me that he also has feelings for Sarah and asked me to help set them up.

I was shocked and conflicted. For background, Alex has always been supportive and a great friend, but I never expected him to like Sarah too.

On one hand, I want them to be happy if they have a genuine connection. On the other hand, I can't deny that I feel betrayed and hurt that Alex wants to pursue Sarah when he knows how I feel about her.

Sarah has shown interest in both Alex and me, but I can't shake the feeling of being stuck in the middle of this love triangle. I value my friendship with Alex, but I also don't want to suppress my own feelings for the sake of their potential relationship.

The thought of setting them up together is tearing me apart. So, WIBTA if I go along with Alex's request and help set up my best friend with the person I like, even though it may hurt me in the process?

I honestly don't know what to do here.

The Heart of the Dilemma

This love triangle isn’t just a simple crush; it’s layered with friendship and potential heartbreak. The OP's best friend, Alex, has thrown a wrench into the mix by expressing interest in Sarah, which complicates everything. It’s one thing to want to support a friend, but it’s another to potentially sacrifice your own feelings for their happiness.

What makes it even more intense is the OP’s emotional turmoil. He’s feeling betrayed and confused, caught between loyalty to Alex and his own unfulfilled desires for Sarah. This creates a rich ground for debate: should friendship take precedence over romantic feelings? Many readers can empathize with this conflict, as it’s a relatable struggle that often leaves one person feeling sidelined.

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That “I was planning to ask her out” plan hits a wall the second Alex admits he likes Sarah too.

OP’s whole heart drops because Alex has always been supportive, so this betrayal feels personal, not just romantic.

For another “ask them out or keep it for yourself” standoff, see the dilemma about setting up your crush with your mutual friend.

Friendship vs. Romance

This scenario highlights a classic struggle in relationships: the balance between friendship and romance. It’s not just about who likes whom; it’s about the emotional investments involved. The OP’s dilemma raises questions about loyalty and selflessness. If he helps Alex, will he resent his friend for pursuing someone he cares about? Or does supporting Alex mean he’s prioritizing that friendship above his own happiness?

Community reactions have likely diverged because some readers may champion the idea of putting friends first, while others might argue that love should take precedence. The tension here is palpable, and it’s a reminder of how messy human emotions can get when feelings collide.

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Meanwhile, Sarah’s interest in both OP and Alex turns every conversation into a countdown to heartbreak.

So when OP wonders if he’s an asshole for helping set them up, it’s not just guilt, it’s the fear of being stuck in the middle again.

We're curious to hear your perspective. Share your thoughts in the comments.

This story illustrates the intricate web of emotions that can entangle friendships and romantic pursuits. It’s a tough spot to be in, where helping a friend could mean sacrificing your own happiness. What would you do in this situation? Would you step aside for your friend’s sake, or would you fight for your feelings? This dilemma is bound to spark conversations about love, loyalty, and the sometimes blurry lines between them.

The Bigger Picture

In this love triangle, the original poster (OP) finds himself torn between loyalty to his best friend Alex and his own feelings for Sarah. Alex's surprising confession not only complicates their friendship but also puts OP in a position where he must weigh his desire for Sarah against his commitment to support Alex's happiness. The emotional turmoil he experiences highlights a common conflict where friendship and romance collide, forcing him to confront whether he can genuinely put his friend's interests above his own. This situation is a poignant reminder of how intertwined emotions can lead to difficult choices, ultimately resonating with anyone who's faced similar dilemmas in their own lives.

If OP helps Alex and Sarah get together, he might end up losing both the crush and the friendship.

Still torn between your crush and your friend’s feelings, read the Reddit thread on playing matchmaker in a love triangle.