Cocktailery: How to Flirt with the Bartender

While I’m working on my first novel, I’m fortunate to have one of the best “real” jobs in the world. I’m a bartender.

Tending bar is a writer’s dream job. I’m surrounded by people all the time. I notice the habits and mannerisms of my regulars. I’ve learned all manner of things and had no end of stimulating conversations with customers. I spent almost two hours discussing The Walking Dead with one of my customers. I got to practice French with two others. Mostly, it’s good for being around people, which recharges my creative batteries.

Another perk of the job: flirting with hot new friends. Lots of guys want to flirt with the bartender, and why not? As my bartending sensei says, “Everyone wants to be the bartender or sleep with the bartender.” Besides, it’s harmless, sexy fun. Purposeful flirting with the bartender – in which you are really hoping to get somewhere – demands adherence to a couple of foundational principles. Some of my hot new friends adhere quite well. Some guys are … well, they don’t. These are the guys I’m talking to.

Today, I want to help you guys out. I’m going to teach you how to flirt with the bartender. It’s not a foolproof method, but it’s a sound basis on which you can build.

Basically, this boils down to two things.

  1. Remember, the bartender is working.
  2. Remember, the bartender is sober.

Let’s take them one at a time.

Remember, the bartender is working.

Most of my hot new friends don’t have trouble with this one. They understand that part of my job is to reciprocate, at least a bit, when they are flirting with me, although I don’t have to tolerate them if they’re being crass, vulgar or just plain rude. They understand that I have to keep track of everyone in the bar, so I can’t just hang out and flirt with them exclusively. And most of them understand not to interrupt me when I am obviously counting something, although I confess that as a bartender, I should be able to count and talk to you at the same time.

So what’s tricky? Endgame. Let’s say you and I have been flirting with purpose, and it looks like things are going well. You don’t want to stay all night, for reasons I get into below. You want to get out while you’re ahead. I, however, am at work. I have to stay here all night. You’re going to need an exit strategy that gets your point across but acknowledges the fact that I am working. Here’s what to do.

Make a good last impression by doing two things. First, leave me a good tip. I’m not saying you have to be extravagant. The average 20% will do the job nicely. Leave me enough to make me remember you favorably without thinking of you as a suck-up. That probably sounds like obvious advice to a lot of you, and I’m glad. But I am still receiving 1% tips from people who are leaving me their phone number.

Don’t get me wrong. Leave me a 1% tip if that’s all I’ve earned. Understand that if I am mumbling “cheap bastard” into the cash drawer, I am no longer receptive to flirting with you.

Secondly, seize the golden opportunity I am giving you when you cash out. I’m going to give you at least two pieces of paper and a pen. I might even give you a little folder. Success! Think of this as the only private conversation you and I will have, and leave me a note. Leave a number. Leave your card. Less is more – a single sentence speaks volumes. “Had a great time.” “See you next Wednesday” (leave a comment if you get that reference). A little something to make a happy memory is all you need.

Remember, the bartender is sober.

The biggest mistake I see men making when they’re flirting with the bartender is that for some reason, they think they have to keep ordering until closing time in order to get somewhere. Not only is that untrue, it’s actually damaging your chances. I know it seems obvious here in SoberWorld, but if you keep drinking like that, you’re going to get drunk. Once you’re drunk, you take yourself out of the running.

So if you take one direction away from this post, it’s this: Know when to stop drinking. Or at least when to slow down.

You don’t have to stay until closing time – I have to, remember, because I’m working – so you can quit while you’re ahead and follow the tips in the first section. Tip me decently, leave me a little note, and go home a winner. You’re not going to impress me by drinking more or by hanging out at my bar until I turn on the “ugly lights.” In fact, you will probably want to be gone before the lights do their worst for our respective appearances.

Bear in mind, once you cross the frontier from cute flirty person to drunk flirty person, a couple of things happen for me as the bartender. First, I have to babysit you a little. I have to keep an eye on genuinely drunk people, to make sure that they don’t hurt themselves or other people, cause damage, become sick, or worst of all, try to drive. Because I cannot legally serve you if I think you’re really drunk, I have to cut you off, which is not making you look hot. Basically, I have to give you more of what my mom calls “the wrong kind of attention.”

In addition, as the sober person, I am watching you flirt drunk. Believe me – drunk people do not flirt well. They just don’t. Seriously, think about this now, while we’re in SoberWorld. Do you want drunk people hitting on you? You know what an embarrassing experience that is to watch, right?

On top of that, you now run the risk that I will always remember you as That Drunk Guy Who Hits On Me. That doesn’t have to be bad – especially if you tip well – but it’s not exactly on par with The Spy Who Loves Me, is it?

Bottom line: If you don’t stop drinking at the right time, or at least slow down, you will lose a lot of control over the situation. As long as you’re not sitting there with an empty glass, I personally am not going to make trouble for you. And you don’t have to sit there all night nursing that one drink if you go out on top with a decent tip and a flirty little note.

So what do you say, neighbors? Do you have flirty success stories and secrets to share? Any word from those who have been behind the bar longer than I have? Tell the bartender all about it.


  1. Well, I give you a lot of credit, Alexa. My only “bartending” experience was behind the food concession stand at the PNC Arts Center in Holmdel, NJ, working for FREE for band parent fund-raisers. I’d stagger home sometime around midnight, covered from head to toes in beer and assorted other organic materials (mostly smashed foodstuffs), usually sweating (because the Arts Center only operates in the summer), and exhausted (because I’d worked a full 8-hour day at my regular job prior to getting to there). The last thing on my mind at any point in the four or five torturous hours I’d spend “behind the bar” would be flirting. With anyone. Except maybe if Toby Keith happened to swing by. But no, the words “bartending” and “flirting” wouldn’t fall naturally into one of my conversations. Good for you. You do all us women proud. 🙂


    1. Well, if my flirting with guys for fun and profit uplifts the gender, then I am bound, most assuredly, to continue doing so. 🙂

      I’m not superhuman, now — I do wake up from time to time feeling like someone’s trying to twist my legs off. But the cash helps. And it is indoors! I don’t know how you were doing that outside in the summer!

      Girl power indeed.


  2. Hey, Lexi! Loved the post! I hope some of those guys read it and took your fine advice to heart. And you are certainly making lemonade from the lemon of having to work two jobs! As you said, lots of great people-watching ops as well as the other benefits. Well done and good luck. Believe me, I’ll be “watching this space” in the future!

    Denise Golinowski/Author


    1. Hey, Denise!

      Yeah, I figure that I may have to work, but I don’t have to be bored. Bartending is the only way to fly in that respect!

      Keep an eye out on Thursdays; I should have something up weekly for your perusal.

      See you then!


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