AdviceHey, Bonita!

Is It Weird to Ask Out My Bartender?

Hi Bonita!

I’ve made a resolution of sorts to be a bit bolder and ask more women out. Though I’m wondering how you feel about men asking women out at work? Every couple months, I find myself having a particularly good connection with a regular bartender, server, cashier, etc. whom I just do not see outside of their place of work. I’ve heard many complaints over the years from friends about dudes hitting on them and asking them out at their job, and I certainly wouldn’t want to make anyone uncomfortable, considering we’ll see each other again a lot.

Is there any way to navigate this without coming off as one of the creeps?


Your friends are correct: Being hit on or actively pursued by customers is uncomfortable as hell for service industry workers, not to mention horribly inappropriate for patrons. There is a distinct power imbalance between customer and server/bartender/cashier. Service industry personnel are paid to be nice to you and make you feel welcome and wanted—that’s just good customer service, and a way to ensure return visits from big spenders. The nicer the server is, the better the tips, but the delineation between customer and friend begins to blur.

The problem is exacerbated by the fact that people who work in the service industry are often treated as invisible: just part of the business, less human than the patrons. It’s easy to forget that your server is a person when everything she does is scripted and kind. So it feels like nothing to corner a server at the end of her shift and ask her out on a date. She’s always nice, so she must like you, right? She’s nice because she’s paid to be nice. Never forget that.

Honey, there’s no way to navigate that situation without coming off as a creep. I work in the service industry, and there’s nothing more terrifying than the customer who seeks you out after work hours have ended. It’s invasive, unwelcome and inappropriate, because there becomes a concern about that customer making trouble for you at work if you’re not receptive to his advances. You think you’re just flirting and making moves, but for the server it becomes a delicate situation of keeping her livelihood intact.

My advice is to never assume that a bartender or server wants more from you than your money. More often than not, that’s true. If she’s genuinely hot for you, she’ll seek you out or slip you her phone number. The safest thing to do is to let her make the first move. Still, I don’t want to get your hopes up about the real intentions behind those friendly smiles.

I’ll be blunt: I got caught cheating. Well, it’s more nuanced than that, but I can’t deny that what I did was wrong. I was caught red-handed, and I’m trying to make amends with my long-term girlfriend. I’ve been reading about polyamory and talking about it with friends who practice, and I want to see if this could be a healthier direction for us to go in after years of back-and-forth cheating.

What do you think about poly? Is it a good change for a chronic cheater?

You don’t cheat because monogamy is a poor relationship model. You cheat because you can’t commit. You make promises, then you break them. I’m sure this pattern is present in other parts of your life. Monogamy is not the problem here; it’s you. A woman who’s been cheated on for years will see the prospect of polyamory as giving her partner permission to cheat in the future.

I think polyamory is the relationship model of the future, and I’ve seen it work for all kinds of different people, but infidelity is the worst way to enter into this practice. It’s still very possible to cheat and destroy people’s trust in polyamorous agreements, and it doesn’t guarantee that you won’t go out and continue to hunt for strange. Polyamory is not a license to cheat. It’s just another type of relationship model that still requires communication and commitment.

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