The Guy’s Guide to Asking Out the Bartender

While surely there is a chance something special exists about you—excessive charm, good looks, wit—it needs to be remembered that the bartender you think is so into you has some of those qualities too, and also works for tips.

That is not to say that when out at a bar the woman on the other side of the counter is only faking her interest in you and everyone else; she indeed is likely being genuine. It’s just wise not to confuse her amiability with curiosity about seeing you socially.

After all, there is a reason the bartender is attractive and chatty: that’s the job. They work on tips, and tend to be of the sociable and confident type. At the same time, though, most bartenders (well, all), do enjoy a drink of his or her own (or four), and are as likely to be single as they are to be in a relationship.

All of that is to say, if you are interested in asking out your bartender, she might be interested as well. In the service industry, however, things operate a bit differently. It’s different than meeting someone at work or through a friend; in fact, it isn’t even like picking someone up at the bar. Instead, asking out a bartender, or really anyone working in the service industry, is a little more complex, for better and worse. Here’s what you need to know.

Talk About Anything

The wonderful thing about the interaction between bartender and patron is that the former will listen, at least initially, to just about anything the latter says. So say something; anything. This isn’t time to play coy, as if you’re smiling across the room to a woman drinking with her friends. Some people go to the bar to sit and drink by themselves, some to socialize with friends. The bartender will chat with you, again for at least a little bit of time, if you want to talk. If you don’t, she will leave you alone. The bar allows for jumping right into any conversation without pretense, so take advantage of the situation.

Don’t Get Possessive

So the bartender is going to talk to you, but she is also going to be talking and having fun with a lot of other people. That’s part of the job. Chances are people will buy her drinks, flirt with her, and visit the bar specifically to see her. You might not know if they are regulars, friends, or those especially interested in asking her out, or even those who already have. It’s completely unfair to get possessive or jealous, not to mention unhealthy, but simultaneously, there is no particular reason to get discouraged. Just because you might not be the sole source of excitement and interest during the night doesn’t mean you can’t be a part of it. Replace uncertainty with confidence, and understand this isn’t her first day on the job.

Don’t Presume

A quick way to lose grasp of the situation is to try and presume what she likes and wants to hear. Understand that she will meet a lot of different people through the course of the night, and to a certain extent, she will smile and chat with them all. Don’t flash money, don’t talk about how big a tip you are going to leave, and don’t assume that just because she is doing shots that you can get her drunk and help influence her decision making. Also, buying drinks or racking up a large bill will ensure absolutely nothing; any expectations you have based on that interactions are unfounded and likely inappropriate. Be yourself, be calm, and focus on the here and now and not what’s happening elsewhere.

Take Your Time

A connection might not develop in one night, and certainly could take time. That’s true of any potential relationship, but the fortunate thing in this case is that you can easily get to know one another. Just because you’re hoping for an exclusive date doesn’t mean that the interactions you have at the bar can’t be worth something. This is true of any rapport in the service industry, be it with a gym trainer or hairstylist. You can get to know someone pretty well through these situations, which may in the long run build a stronger foundation. Maybe you’re looking for someone to go home with that night; but if you’re genuinely interested in dating and something beyond, it may take a few tries, but can be well worth it.

Be Yourself

Ultimately it all comes to this. Get to know the one you’re interested in without presumption or speculation, and everything will unfold naturally. Any bartender you’re interested will so easily and so fast see through your façade. Find earnestness and confidence, two qualities that will go a long way in capturing and holding attention. If you’re interested in a bartender, chances are you aren’t the only one; the only thing to do is summon some courage, engage, and be yourself.

Anthony Marcusa is a Toronto-based freelance journalist whose writing dabbles in film, TV, music, sports, and relationships – though not necessarily in that order. He’s simultaneously youthfully idealistic and curmudgeonly cynical. You can follow him on Twitter @MrAnthonyWrites.


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