Ask Dr. Nerdlove by Harris O'Malley

How Do I Ask My Bartender For a Date?

DEAR DR. NERDLOVE: I wanted to reach out to you because I’m seeking guidance on a potential relationship, but am uncertain of how to proceed.

About 2-3 years ago, I went with a friend to a nearby bar, which featured a “Taco Tuesday” special after we had both seen “Sorry to Bother You,” and wanted to discuss it further. Needless to say, the bartender working that night was sociable (especially once I showed an interest in her work and craft) and overall it was a good time.

A year or so later, I came back to the bar one night to meet some other friends. Once again, she was working there and seemed happy to see me. We caught up a bit, and much to my surprise, comped me for one of my drinks, which was sweet and generous of her. This back-and-forth carried on throughout the rest of last year. I’d show up, eat, drink, tip generously, and talk. It turned out we had a good amount in common: she’s a photographer, I crew on film/video jobs. We both love talking mixology and different liquors and liqueurs.

In short, I developed a bit of a crush on this bartender. And after introducing her to some of my friends, they also picked up on a potential mutual interest vibe. So near the end of last year, I expressed an interest in hanging out with her outside of her workplace. She, much to my surprise, gave me her cell phone number and seemed willing to meet. She did express a desire to keep it casual, however, although that was not a deal-breaker for me. As someone who has to be friendly and sociable to keep working, making friends is always easier and slightly more comfortable to me.

So I reached out to her at the beginning of this year to see if she wanted to get coffee. She did text back that she was in favor of it, but we never got a date or time pinned down, so I let it go, not wanting to pressure her. Fast-forward to now, where I stopped into her bar for a meal and some drinks. She was working there and seemed very happy to see me, so much so that she came around the bar to sit next to me as we both talked about our lives. At this point, even I felt like there was some kind of chemistry between us, and this was before the liquor started flowing.

Later on, I sent her an invite by way of a text message to a casual event among friends, but she didn’t respond, though I didn’t take it personally. Given her desire to keep things simple, I figured pushing her for an answer wouldn’t be helpful.

So in summary, I’ve been interested in getting to know this bartender a bit more outside of the place she works. We have common interests and goals, and seem to get along well enough when at her workplace. The question is where the boundaries for this relationship are.

If it can be romantic, that would be fantastic. If it’s more of a friendship, I would also enjoy it greatly, since I find myself cherishing those the most. If it’s more of a casual acquaintance-type of deal, I also would be willing to accept it, since the matter would be settled. The issue comes down to asking whether there’s room for this relationship to grow at all outside of the bar.

I’ve read enough articles and essays to know how often women have to be diplomatic when refusing the advances of men, and the difficulties of navigating that space safely. Therefore, I’ve tried to avoid overstepping my bounds with her or violating what trust I’ve earned.

Any advice or help you could provide here would be greatly appreciated.

Thank you,

-Searching for Boundaries

DEAR SEARCHING FOR BOUNDARIES: So, there’s a couple things going on here, SfB.  But before I get to your question in specifically, I want to talk a little about flirting with folks in the service industry, especially bartenders, waitstaff and the like.

While a lot of folks have issues with “is she flirting or just being friendly”, this can be particularly fraught when it comes to flirting with your bartender, your waitress or other people in service jobs. There’re a lot of things that will be working against you — both in terms of gauging her interest but also the likelihood of her being interested in you at all.

The first is that you’ve been flirting with someone in the service industry and, in particular, someone who makes a living off customers’ tips. This is something that guys in general need to keep in mind when they’re flirting with waitstaff, bartenders, shot girls, strippers and other folks who make money from tips and commissions; they have a vested interest in appearing available and interested. That means that she has a vested interest in being “professionally” flirty. By being a little friendlier and flirtier, especially with male customers, she increases the likelihood of getting more and larger tips from folks. Some will be from people who think that that they can essentially “buy” her affections, others from folks who’re likely to give more money because they’re turned on. It may feel like they’re into you… but a lot of times that’s a case of wishful thinking and letting your dick do the thinking for you. It’s important to keep a relatively level and skeptical head in these situations.

There’s also the fact that she’s at work, and in a position where she can’t be as straight-forward with turning somebody down. While there is a movement for more venues to implement “have your staff’s back at all times” policies, there’re still plenty of managers and bosses who’ll fire an employee who’s “causing trouble”, even if the trouble in this case is a customer who’s acting like a double-stuffed dickbag. So the odds are high that you’re going to get a very soft “no” – being turned down in an indirect manner. This may be a “I can’t this week”, “I’m too busy” or even a “we have a no dating customers rule”. This sort of refusal helps ease the sting of the rejection and soothes the potentially ruffled feathers of a customer who might have a profoundly negative reaction to being turned down.

The next thing to keep in mind is that as an attractive woman in a front-of-house job like bartending, she’s getting hit on a lot. There are a lot of men who are going to be throwing attention her way, and that can end up being both exhausting and tedious; doubly so because frankly, a lot of the folks hitting on her are douchebags who don’t give a six-legged rat’s ass that she’s, y’know. At work. So while she may be the most attractive woman you’ve ever met and you’ve never done anything like this before… you’re likely not even the fourth or fifth person to hit on her that day. Being yet another dude throwing dick her way makes you blend into the crowd of all the other folks who’ve made the same offer.

Now this doesn’t mean that approaching or flirting with with the waitstaff or the bartender (or whomever) is impossible; it just means that you shouldn’t, as a general rule, expect more than just some enjoyable flirting.

(And also, tip them well; they’re working hard for their money and service industry wages are a goddamn crime.)

It is possible that you and someone in the service industry might make a solid connection that could lead somewhere… but it’s going to take time and a lot of careful behavior.

Much like in your case SfB: you basically did everything right if you want to build a connection with a bartender. You became a regular, which mean that she got to know you over time. As many an advertising executive can tell you: repeated exposure breeds familiarity and familiarity breeds interest. You also made a point of being the sort of customer that waitstaff and bartenders like: you’re polite, you’re friendly, you show interest in them as a person and — importantly — you respect their time. You tip well, you’re well mannered… these are these are the sorts of things that makes somebody a favorite regular.

Once you’ve built up that respect, affection and — importantly — trust over time, then and only then did you make an offer to get together outside of work. And even then… you did it all correctly. You didn’t treat not being able to make a date work as anything other than an unfortunate case of bad timing and incompatible schedules. You didn’t push her, get angry or otherwise act like an asshat. All to the good. This is a big part of why she’s still happy to see you when you come in.

The only mistake that you made — as far as such things go — is that you invited her to a group event. While that’s not necessarily a bad thing — in fact, it can work out rather well — it can also be more than a little intimidating for some folks. Going to an event where you only know one person can be a little much, especially when you don’t necessarily know that person well. It can be intimidating if they’re a little on the shy side (which yes, even folks with social jobs like bartending can be, especially when they’re not in work mode) or exhausting if they’re an introvert. And some of it might have been an issue of “private event” vs “public event”. If it were you and some friends going to something that was open to the general public, that might be more acceptable than if it were a casual get together at somebody’s house; it’s entirely possible she might have felt like an outsider or intruder.

Or it just may not be to her taste. Or… well, she just might not have been interested.

But again: you’ve handled this well, and that says a lot of good things about you.

Here’s what I’d suggest: give it one more shot with your bartender friend. This time, the next time you hang out that the bar, bring up something that you’re planning to do anyway: a concert, an art show, a street-faire… something that you enjoy and would go to regardless of whether you have a date or not. Then, towards the end of the evening when you’re planning on heading out… tell her that you think she’d probably really enjoy $COOL_THING and if she’s interested, you’d love to take her. This has a number of advantages over inviting someone to a casual get-together with strangers: there’s a specific time and place, it’s lower emotional stakes and it feels less serious. It’s a public event, which can feel both safer and less intense, and it doesn’t feel like as much of an investment.

If she’s down… well, Yahtzee; you both win. If not? Then assume that this was a soft “no” and that while she likes you as a person and a regular at her bar, she’s not interested in taking things outside of work. You can take satisfaction with having not thrown away your shot and in having gotten an answer. By respecting the soft no, you’re respecting her and not making things awkward and having to find a new bar.

And if it is a case of her being interested, but circumstances have worked against you? Well, she knows you’re into her and that you’re a cool and respectful dude. She’ll let you know if she’s down for this being more than just a bartender/favorite customer relationship.’

Good luck.

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