Is it appropriate to ask out my crush if I only ever see her at her job?

Question

I've known this woman for slightly over a year, however we only see each other once a month when she cuts my hair. Over the last few months it feels like we've started flirting, although I could mistake being friendly and a mix of wishful thinking for flirting. I'd like to ask her out, or at least better insinuate that I'm interested in her to see how she feels, but only if it isn't clearly inappropriate to do so.

The only good example I can share is that the last time we had an appointment she mentioned that she hates answering clients questions about herself, and when I joked that this is exactly what I was doing and I'd stop, she laughed and said it was okay that I did it.

When I was younger, I would have set my feelings aside. However, being nearly 30 I've started to reevaluate what I want out of life and how to achieve it, and part of that is knowing I need to be more direct about pursuing a relationship. I'm also aware this is a childish question for someone almost 30 years old, but I've dated very little and I'm making these personal life changes for that reason. I just don't know what is and isn't appropriate based on context, beyond the general rule of don't hit on someone while they're working.

Oliverlogan263 · Accepted Answer

Bro, that's a tricky situation for sure. I can see why you're feeling a little unsure about whether it's appropriate to ask your hair stylist out. On one hand, you've got this connection and it seems like there might be some mutual flirting going on. But on the other hand, she's technically in a professional relationship with you as her client, so you don't want to cross any lines.

The way I see it, there's no easy answer here. It really depends on how you approach it and how much you value that professional relationship. If you were to ask her out, you'd have to be super respectful about it and make it clear that you don't expect anything and that you're cool with her saying no without it affecting your business with her.

Personally, I think I'd try to feel it out a little more first. Maybe next time you see her, try to steer the conversation a bit more towards personal topics and see how she responds. If she still seems open and engaged, then you could try something like "Hey, I was wondering if you'd be interested in grabbing coffee/dinner sometime, just the two of us?" Make it casual and low-pressure.

But if she seems at all uncomfortable or puts up any kind of boundary, I'd definitely back off. You don't want to put her in an awkward position or jeopardize the relationship she has with all her clients. That professional dynamic is important, and you've gotta respect that.

At the end of the day, it's a tough call. You've gotta weigh the potential upside of asking her out against the potential downside of making things weird or messing up your business relationship. Only you can really decide if it's worth the risk. Just be super mindful and considerate about it, and don't push too hard if she seems hesitant.

Good luck, bro! I hope it all works out for you, whatever you decide to do.