The Compass  /  (Renaissance Man)ual  /  How to Buy a Lady a Drink

How to Buy a Lady a Drink

Pickup lines not working? Buy a lady a drink.

You’re at the bar and a woman catches your eye. But how do you make that initial contact?
Pickup lines are tacky. Have some class.

The better move, in our opinion, is the simple act of buying her a drink. After all, actions speak louder than pickup lines. Of course, in the modern world of online dating (and the multi-billion dollar online matchmaking industry behind it), meeting women face-to-face is a becoming a bit of a lost art. This is, by no means, the only method of meeting women. Still, knowing the proper way to buy a lady a drink is a useful skill, and one that takes more finesse than swiping right.

Know Your Numbers

There are a myriad of situations in which you might find yourself wanting to buy a lady a drink but there is one thing you should always consider before going forward and that is the numbers game.
Here’s how it breaks down.

One on one

One on One

Let’s say you’re flying solo and she is too. In that case you’re good to go. Yes, she might be waiting for her husband/boyfriend/significant other, but if so and you send a drink her way, no harm no foul. If she is waiting for, say, her husband and refuses the drink she’s still likely to be flattered and isn’t likely to send Butch over to kick your ass when he arrives the way she might be if you had approached with a barrage of cheesy pickup lines.

They’ve got you outnumbered

They've Got You Outnumbered

When there’s a gaggle of hotties at the bar and you’re on your own, sending a drink to one of them is a little bit tricky. You’ve got to make sure it reaches the intended target, for one. Plus, there’s the awkward situation you create with her not-as-hot girlfriend. It’s not an impossible move to pull off, but it’s best tried when you’ve established at least a little flirtatious eye contact with the recipient first.

The fast break

The Fast BreakWhen it’s two or three on one, i.e. you’re with your crew when you spy a lovely lady sitting alone at the bar, sending a drink over is not good form. It can seem aggressive and intimidating for a woman to be approached by what looks like an entire crew.

All even

All EvenThis one’s a no brainer. When you and two of your buds want to get the attention of a trio of ladies, buying them a round is a great way to get the ball rolling.

Who needs a pickup line when you know how to buy a lady a drink? (Knowing how to dress doesn't hurt either.)

Part 1 – The Order

This part needs little explanation. You know how to order a drink. The main thing to remember here is decorum. Don’t order a Scotch and send it over to the lady sipping the wine spritzer in the corner. In fact, don’t order any specific drink. Just tell the server that you’d like to get her another of whatever she’s having and leave it at that.

The beauty of this move is that it allows you to be tasteful and a bit brash at the same time. Tasteful, because you are not walking over with a shotgun full of pickup lines and firing away, but brash because you’re still making the first move and making your intentions known. It shows that you’re a man who knows what he wants and goes after it, but you still play by the rules. Speaking of rules:

Rule of Engagement #1 – Match your environment

You may have noted that we titled this story How to Buy a Lady a Drink. You don’t buy a girl a drink. Girls are too young to drink. You buy a drink for a lady. That is, someone with the sophistication to appreciate a bit of class. If she’s doing jello shots and yelling at the umpire on the big screen TV at your local sports bar, she may be your ideal woman (and by all means, go for her), but she may not appreciate an excellently mixed Sidecar from the gentleman in the suit at the other end of the bar. Our point: Be picky about how you use the approach we’re suggesting here.


Part 2 – The Delivery

When you order the drink, keep an eye out for the server delivering the drink. Any server worth their salt will politely inform the recipient that the drink is from you without making a big scene out of it. When that happens, if you’ve got a killer smile, use it. But flashing the pearly whites is not mandatory. It can make you look like a creepy doofus if you’re over at the other end of the bar grinning like you’re posing for a yearbook photo. Remember, classy is the name of the game here. All you really have to do is simply raise your glass and maybe mouth the word cheers.

Rule of Engagement #2 – It Doesn’t Entitle You to Anything

It’s not tit for tat. You may have bought the drink. She may have accepted as a courtesy. Don’t assume that the drink buys you anything, not a conversation, and certainly not a phone number.


Part 3 – The Follow Through

Look for signs that you’re invited. A come hither gesture is ideal, but a warm smile will do. Once you get the green light to approach, have something to say when you arrive. It doesn’t have to be scripted (in fact it shouldn’t be), just be ready with a few talking points to answer the question “why did you buy me this drink?”

Rule of Engagement #3 – Don’t Get Her Drunk

The goal is to open the door, not challenge her to a drinking contest or push her to the point where she won’t remember you the next day. While you’re at it, don’t you go and get wasted either. If after sharing a drink with you, she’s thirsty for more, scale it back a little. Keep drinking water and making conversation so you don’t just guzzle the next one down. Or implement your “exit strategy.” But that’s another article altogether…

quote This one's the guys in the killer suits.

Want to go try out some of what you’ve read here?
We’re here to help.

We may not be able to give you mad game when it comes to roping in the ladies, but we can give you expert advice on how to present yourself in the best light when you’re on the town. So if you want to dress like the dashing dudes you see in the photos above, just drop us a line at concierge@blacklapel.com and we’ll set you up with the some key parts for your wardrobe.

And if you want to discuss the technique above (or just want to tell us your favorite back-up pickup line), leave a comment below.

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4 thoughts on “How to Buy a Lady a Drink”

  1. Dave Bowden says:

    Thanks for the shout out guys! Wish I had a step-by-step guide like this back in my single days…

    1. Black Lapel says:

      Ha! Don’t we all…

      Thanks for reading, Dave!

  2. Black Lapel says:

    Feeling too shy to try anything you saw above? Writer Dave Bowden, aka The Irreverent Gent, recently shared a bunch of techniques for overcoming shyness. One tip, remembering you’re not alone. “I was so fixated on the (very) small number of people who actually are naturally social,” he writes “I couldn’t see the hundreds of average, introverted and shy people lined up behind them.”

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