Buy a stranger a drink

How to Buy a Stanger a Drink in Style

How to Buy a Stranger a Drink in Style

It’s probably happened to you before. You’re sitting at a bar, enjoying a cocktail and a cigar, and in walks someone that catches your eye. She’s cute, she’s well-dressed, and she looks like she’s alone. You want to impress her… so what do you do? Do you walk over uninvited?


The answer is: you buy her a drink.


One of the keys to buying a stranger a drink is to make it seem smooth, and not creepy. You can buy someone a drink and look cool while doing it, making sure she’ll want to talk to you and not run screaming in the other direction.

Here’s a guide for buying a stranger a drink in style.

Step 1: Confirm That She’s Not on a Date

When you send someone a drink, she can be out with friends. But it’s not cool to try to woo her with a beverage if she’s currently out on a date. Try to gauge the scene by watching what’s going on. If you can’t tell, ask the bartender.

Step 2: Wait Until She Needs a Drink

The second step to buying a stranger a drink is making sure she needs a drink. Pay attention to the level of liquid in her glass, then only send her a drink when it’s low. You don’t want to inundate her with alcohol (or accidentally send the message that you want to get her drunk).

Step 3: Send Her What She’s Drinking

Talk to the bartender, and tell him that you want to send the stranger a drink. Tell him to make her another one of what she’s drinking. If he doesn’t know, you can tell him to ask her what she wants and charge you for it. Don’t send her anything high in alcohol, like a Long Island Iced Tea, because again, it will look like you want to get her wasted. If she’s only drinking water, send her that.

Step 4: See How She Reacts

If you can see the stranger, watch her reaction to getting the drink. Is she pleased? Does she seem creeped out? Choose your next move based on how she’s reacting. If she doesn’t seem happy, you can know that you tried and it wasn’t meant to be. If she seems happy and curious, go over and introduce yourself. See if she makes eye contact with you and tries to interact–these are good signs that she is interested in learning more about you.

Important Tips

To send a stranger a drink in style, keep in mind these important tips:

  • Don’t deliver the drink yourself. She may worry that someone slipped something into it.
  • Don’t be pushy. If the stranger doesn’t want to accept the drink, let it go. Being pushy will only make you seem threatening and intimidating.
  • Consider sending a message with the drink. Write a little note on a napkin or tell the bartender to repeat something to the recipient.
  • Drink a classy cocktail yourself, in case she comes over to talk. You can get drink inspiration from cocktail influencer and bartender Rael Petit.

To make sure you look good every time you’re at a bar in case you find the right stranger, get your hair cut at the Barber Surgeons Guild. We can ensure that your hair is as groomed and fashion-forward as possible, so you can impress even without having to buy someone a cocktail. Get style advice in advance from influencer Allen Walker.

For more guidance on how to live the coolest life possible, check out our lifestyle magazine. Or, if you want to get better at picking up girls or dating, read what dating coach Johnny Cassell has to say.