Wingman Approved or Unapproved? You Decide.

Buying a Woman Drinks


Clients ask me this all the time and I am going to put it to rest NOW. When it comes to buying a woman a drink, NEVER BUY A WOMAN A DRINK.

I know women out there are upset and that’s ok. I don’t care. There are reasons why I say this. It’s all about context. And here’s why.

Wingman Unapproved

Don’t buy a girl a drink within five seconds after meeting her. While no woman will REALLY refuse a free drink (in fact, women spend little amounts at bars for this reason alone), the moment you offer her one, it’ll only mean one thing. Even if this is not what you are trying to say, you are still saying this,

“You are hot. I know nothing about you, but I am willing to buy you a drink in hopes that I can validate myself to you. Also, you’ll be a little more liquored up and so maybe more likely to let a guy like me talk to you.”

It’s pathetic. You buy the drink, she takes it and then stands there, hoping that you’ll just walk away. She’s not really going to walk away until the drink is finished because she feels bad and it’s rude so she’s willing to give you at least the time it takes her to finish the drink. Yeah, you can win her over in that time, I suppose, but you’ve already put the odds against you from the start.

Also, don’t offer the girl you like a drink and not her friends. That is just not cool. If you ever want to be cockblocked, pull this move and it’ll be 100% effective. Why would you NOT offer her friends a drink? Is she THAT special that only SHE deserves the benefit of getting a drink from you out of the entire group? Want to know what you say then?

“I’m a douchebag.”

Either of these moves will be a #fail.


Wingman Approved

If you must buy her a drink, if she’s with a group, you are buying everyone a round. Personally, if you have the ulterior motive of trying to get with the girl, it’s not worth the investment of buying everyone a drink. BUT, if what you are trying to say is,

“You guys are cool, let me buy a round for you guys,”

and you actually mean it, then it’ll look SO much better.

Another situation of buying a girl a drink would be if you two were alone, whether isolated from friends or going over to another bar that night. Obviously, it’s been insinuated that the two of you would like to get to know each other in more of an intimate environment. If you are going to buy yourself a drink, it makes sense then to buy her one as well. It’s a good gesture and because you two have already gotten to know each other a little bit, the thought expressed above will less likely run through her head. Why? Because now you are having conversation over a drink as opposed to drinking over a conversation.


Pretty simple guys. Save your money or spend it on yourself.

*Wingman Approved/Unapproved is for entertainment purposes only. This is NOT advice and is only produced to evoke fun discussion and conversation. Misinterpretation of this as advice and using it in a social environment may result in brutal rejection, a drink thrown at you, a punch in the face and/or a huge social value drop. The Professional Wingman is not responsible for such misinterpretation.

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