The Dos And Don'ts Of Hitting On A Hot Bartender

In the most general of senses, I'm largely tone deaf when it comes to picking up signals from women.

I've been known to respond “That sounds good” when asked by a frustrated girl at a bar, “Aren't you supposed to ask me out to dinner or to get drinks sometime?” (Shockingly, that relationship didn't last long.)

I've answered texts incorrectly, misread tone through email, thought a girl couldn't stand me when she actually liked me and, more often, the exact opposite.

It should come as no surprise then that dealing with female bartenders is a complete mind-fuck for me.

How are you supposed to be able to discern the difference between genuine affection and interest, and the affected air of someone looking to make money off your tips?

When does it cross the line in your favor? And what do you need to do in order to get it there?

Luckily for you, I happen to have done some research.

A friend of mine (let's call her Donna, because no one my age is named that, so it's clearly fake) is an attractive bartender.

Donna's been hit on and done the hitting on... she's seen what works, and, more importantly, what definitely doesn't.

These aren't one-size-fits-all guidelines from her, to be sure, but they're a lot more useful than going in there blind.

Here are the do's and don't's of hitting on your scorching hot neighborhood bartender:

Do:

Be aware of who else she's talking to at the bar, how much time she's spending with them and how much she's laughing at your jokes as opposed to others.

Some bartenders (just like some real-life women!) are naturally gregarious people. Meaning: They laugh at things people say with relative frequency and ease. Others, not so much.

If the woman you're talking to seems to be paying you an inordinate amount of attention and laughing at your jokes more than normal (you know, obviously flirtatious signs) it's a good start.

Not the whole ball game, but a good start.

Don't:

Look.

Seriously, try your best not to stare at this gorgeous, drink-serving specimen. I mean, I get it. It's tough. Hell, I spend most of my waking moments out with women trying to not look.

But I can't stress this enough: just because she's wearing an outfit that could at best be described as skimpy, and at worst, wildly indecent, it doesn't mean you have the full right to stare at her chest.

In the words of Dave Chappelle, just because she's dressed a certain way, doesn't mean she is that way. Have some class.

Respect the hustle of a bartender and what she's up against, and do her the courtesy of not ogling. Trust me, it'll be noticed. And it will help.

Respect the hustle of being a bartender and what she's up against, and do her the courtesy of not ogling.

Do:

Ask specific questions... like you would on a normal date or when trying to get to know ANYONE else.

Ask about her family, friends, passions and hobbies. Get to know the girl outside of her outfit, her job and what tequila she prefers.

And under no circumstances should you ask her if this is "her main job."

Even if it is — which, frankly, is awesome, since a lot of bartenders net more money than I make — this is an astonishingly insulting question. And it's one that is asked way more often than you think.

Don't:

Be sloppy.

A lot of times, the haze of alcohol provides confidence that things are going better than they are. Reality: they aren't.

She's seen all kinds of drunken messes belly up to her bar — likely, there's been several that very evening.

That's work to her. This shouldn't be. So hold your liquor, homie.

Do:

Ask if she'll do a shot with you.

Not because you're a drunk, or you're trying to get her drunk. Do it because it will give you a sense if she's actually enjoying your company. If she buys the shot, even better.

My personal suggestion: Suggest something light, so it doesn't seem like you're just trying to get her sauced.

Don't:

Ask for her number by saying something like, “You're really hot, can I have your number?”

That's idiotic, patronizing and objectifying. If you seriously can't do better than that, just go home and drink by yourself.

I don't care how lonely that sounds. 

Do:

Wait until the end of your night to ask for her digits. If it fails (and it might), at least you won't have any more awkwardness to endure.

And do be direct. Find a common interest throughout your conversations, and then make that the point of your asking ("Since we both like music, I was wondering if you'd like to go to a show with me sometime...").

Don't:

Ask her to hang out that night or after her shift. It gives the not-so-subtle impression you're only about hooking up.

And while that may be both of your intentions, have the decency to at least not be so blunt about it.

Do:

Ask to go on a proper date.

Just because the environment is filled with alcohol and drunkenness and push-up bras doesn't mean you should be any less of a gentleman than you would be if you met a girl at the library.

This is a decent society (for the most part). Act accordingly.

Don't:

Try to get her number or ask her on a date and then leave less than a 20 percent tip.

This seems obvious, but it's worth stating. You're not buying her affections, but if she's already bought you a few drinks (a good sign), don't be a stingy douche.

Frankly, unless you find her (or any server, for that matter) spitting in your drink, tip at least 20 percent. Don't be a schmuck —they live off that money.

Unless you find a bartender spitting in your drink, tip at least 20 percent.

All in all, like most things, the answer here is fairly straightforward: Treat this woman like you would any other female in any other situation.

Be polite and engaging, look for signals, try to be direct and have some courage. And, most importantly, tip well.

And don't stare.

God's speed.