I matched with my hairdresser on Bumble… Should I ask her out or keep enjoying my awesome haircuts?

arjames

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Sometimes, life puts you in a situation where your personal and professional lives mix unexpectedly. This is the problem I, a 36-year-old man who never thought a haircut could be complicated, am facing.

It began with a swipe. I was scrolling through Bumble, a dating app I don't usually take too seriously when I saw her profile. It wasn't just her appearance—though, I admit, she's beautiful—but her style and interests caught my attention. It felt strangely familiar, like looking at myself. She had a unique vibe that made me break my habit of swiping without much thought. I sent a message for the first time in a long while.

You can probably guess what happened next: no response.

At first, I wasn’t shocked. The number of men compared to women on dating apps can make getting a reply seem unlikely. I just let it go and moved on. But then, something in her profile grabbed my attention: her job. She’s a barber and not just any barber—she works at a place I’ve walked by many times. This made me think. I’ve been looking for a barber I can trust for a long time. Why not try her shop?

Here’s where things get tricky.

The First Haircut
I made an appointment at her shop, not knowing what would happen. When I walked in, I wasn’t sure if she’d recognize me from Bumble. If she did, she didn’t show it. She welcomed me warmly and gave me what might be the best haircut I’ve ever had. During the session, we talked casually about music, hobbies, and her path to becoming a barber. She was easy to talk to, professional, and didn’t give any hint that she knew me.

When I left, I was certain of one thing: I would return. She’s an incredible barber, and after years of average haircuts, I finally found someone who understands what I want.

But there was something else on my mind: I wanted to ask her out.

Why This Seems Complicated
First, let me clarify—I don’t want to make anyone uncomfortable. Respecting boundaries is very important to me. If she didn’t recognize me from Bumble, that’s fine, but what if she did? Showing up at her workplace could seem creepy, and that’s the last thing I want to be.

I also started to consider the consequences of asking her out. If she said yes, it could be great, but what if she said no? Would it make future haircuts awkward? Even worse, what if she felt pressured or uncomfortable seeing me again?

Each time I try to get myself excited to ask her out, I keep thinking about these worries.

Why I Should Take a Chance
Here’s the deal: life is brief. And sometimes, when there’s a hint of interest—or even just the possibility of it—you should give yourself the chance to see where it goes. I’ve thought about our talks, and while I didn’t feel a strong romantic connection, I also didn’t feel rejected. She seemed really into our conversation, and it felt… nice.

I also think it’s important to be truthful. If I do decide to ask her out, I’d do it in a way that lets her say no easily. Something like:

“Hey, I know this might seem sudden, but I enjoy talking to you, and I was wondering if you’d like to grab a coffee sometime? No pressure if you’re not interested—I completely respect your space and don’t want to make things uncomfortable.”

The Benefits of Staying Silent
On the other hand, staying quiet has its advantages. She’s an amazing barber, and I wouldn’t want to lose her services. Plus, there’s a sense of calm in knowing I haven’t overstepped any boundaries. Sometimes, simple things are best left uncomplicated. Perhaps I should just let this pass, considering it a missed chance.

What Should I Do?

This is where I’m unsure. Part of me says, “Go for it.” The worst that could happen is she says no, and I find another barber. The best-case scenario is that it could lead to something wonderful. But another part of me—the more careful part—suggests I leave it alone. After all, she’s in a professional environment, and I don’t want to make her feel uncomfortable.

For now, I’ve decided to stay calm. I’ll continue going back for haircuts and watch for any signs that she might be interested too. Who knows? Maybe something will guide me in the right direction. Until then, I’m just thankful to have found someone who gives excellent haircuts—even if she also makes me think too much about every encounter.