If it seems like your server is flirting, should you ask them out?

What is the difference between someone being polite, and being flirty? Should you hit on someone in the service industry? To get the answers to these questions, I wanted to find a good jumping off point, and I think I’ve found it in the question below (which has been edited for clarity and brevity):

How can you tell if a server that is flirting is tip flirting or interested flirting? I have a server at my regular spot that seems to be flirting with me lately. 

Occasionally, she doesn’t charge me for my beers, and has started becoming far more chatty with me.  The last time I didn’t get her as a server, she kept telling our server what my preferred beer and wings order was from across the restaurant, waved hello at me, and now she always comes over to say “hi” even if she’s not my server.
Fast forward to last night when she saw me walk in, made sure she got my table, had a big smile on her face, and generally seemed happy to see me. I never had to tell her want I wanted the entire night because she would just bring it, and then at the end of the night she only charge me for half my stuff while my friends were charged full price.
I never want to hit on servers because I know they get hit on a lot, but I can’t help but think she is actually flirting.

One of my favorite bars is one that, if one of the owners is behind the bar, I’ll get a buyback. I love a buyback as much as the next guy, but never in my many years of living and dating in NYC have I ever gotten a buyback on a beer or drinks that was a sign that a bartender was flirting with me. A buyback alone, or free food or drinks alone are not a sign that someone isn’t flirting with you. It’s the sign of someone who values you as a customer.

I walked into a bar about two  weeks ago, one that I had been to fairly infrequently. The bartender recognized me from the last time I was there, when he and I, a friend, and another bartender had a shot of a coffee flavored spirit (I legit can’t remember what was in the shot), and asked if I wanted another one. I sincerely doubt he was flirting just because he remembered a shot I took. A good memory is sometimes just a good memory, and not someone going out of their way to remember you.

On average I go to the same diner about 1-4 times a month, usually over the weekend. Me and my girlfriend usually get the same order (Cinnamon roll pancakes for her, some random assortment of eggs, meat, potatoes and/or toast). No one knows my name in the place, but we’ve got a couple of servers who chat us up briefly when we come through, say hello, all that jazz. I’m 100% certain that none of the guys who chat us up are flirting with me. Sometimes customer service and attentiveness even when someone isn’t directly serving you is just that, and not flirting.

I wanted to give some examples from my life that go to show that what might be flirty to you, might just be good customer service and relations if you’re in the service industry. If you work in an industry that, right or wrong, requires that you live and die by tips, it may lead to you coming off as very friendly which people might confuse for flirting. If you’re wondering whether someone is flirting, versus just being friendly, look at someone’s behavior with a critical eye. Which I want to do with the situation above.

To start, and to save you some time, I do think that the woman described above is flirting. Here’s three reasons why:

She singles you out for regular, preferential treatment. This isn’t much on its own, because you’re a regular, and maybe your friends aren’t, so she’s just looking out for her regular. That said, you seem to get a lot of focused preferential treatment. A buyback is one thing, a half price bill is a whole other thing.

She’s going out of her way to be friendly when it doesn’t directly benefit her. It’s one thing to be friendly, and hell even flirty, when you’re the one who stands to gain. If she’s going out of her to be friendly and it won’t benefit her, that’s a good sign.

Let’s assume that I’m wrong, and it does benefit her because everyone pools tips. In that case…

Going out of her way to come into contact with you. I’m sure you’re a good tipper, but I get the feeling that you’re not exactly tipping hundreds of dollars on a $50 bar bill. I’m sure you tip well, but I doubt you tip in such a way that getting your table makes or breaks her night. She seems to be going out of her to come into contact to you, whether by directly requesting to be the server at your table, waving at you from across the bar, and even interjecting herself into your orders.

The case could be made that all three things are not her flirting, but I feel confident saying that she’s very likely flirting with you. So…now what?

For starters, you need to acknowledge that asking someone out can be awkward, that it’s especially awkward when they work in an industry that pretty much requires friendliness, and if they reject you it can be awkward. In the situation above, imagine how awkward it would be if he read it wrong (and I was wrong), he asks her out, she says no, and it’s his regular spot. Just, keep it in mind before you pursue someone who works where you like to go regularly.

If you can avoid it, it’s always better to ask someone out outside of their place of business. This is not me telling you to wait outside of someone’s job to ask them out, that would be kind of creepy. But, if you know you’ll see them outside of work, ask them out there. If you can’t avoid asking them out where they work, at the very least you can ask them out after they’ve stopped serving you. Could you imagine having to reject someone, then giving them a check immediately after? That’d be weird as hell.

Lastly, and this is what I did on the very rare occasions where I asked someone out who worked in the service industry: slip them your card. The last time I asked someone out this way, I wrote my number on a receipt, wrote a note that said something to the effect of “Not sure if you’re interested, but I’d love to take you out sometime. If you’d want to go on a date, shoot me a text. If you’re not interested, no worries” and that was that. This maybe isn’t the most ideal way to ask someone out, but I think it’s harmless, and that’s the point. If someone was interested, they can text you. If they weren’t interested, they don’t have to say anything and can just passively reject you.

If you feel like your server, your local barista, or even your mechanic is flirting with you, they just might be. They might not be though, so look out for signs that point to more than just good customer service. If you come to the conclusion that they’re flirting, want to ask them out, the very least you can do is do so in a way that doesn’t put them in an uncomfortable position.

Good Luck Out There.


Also published on Medium.