Show of hands: How many of you have ever been in this position — a guy offers to buy you a drink, and, even though you’re completely uninterested in him, you still kinda want that drink?

I see.

And how many of you tend to accept the drink anyway?

It’s okay, you know. After all, you deserve a damn drink once in a while. And just because a guy wants to buy you one, doesn’t mean you owe him anything. Right?

Well. Yeah. But where is the line between just accepting a drink and committing that much maligned dating faux pas, leading a guy on?

Related: 6 Really Unnattractive Things That Women Do When They’re Drunk

Speaking as a dude, I certainly have my opinions on this, but in the interest of fairness, I figured I could use a female perspective. So, I asked rock and roll dating blogger and professional badass, Rachel Khona for her two cents. Here’s what we came up with.

When It’s Okay:

1. If the guy’s Daddy Warbucks
Hey look at this guy! Somebody had a big day at the track, huh? Look at him flashing that fat billfold around like everybody’s rich uncle. If this guy wants to buy you a drink? Take it. It probably means more to him than it does to you.

Related: Are You “That Guy?”: 15 Surefire Ways To Tell

2. If he’s buying drinks for the group
If you’re hanging out with your friends and you just happen to meet his group of friends and they just happen to offer to buy a round? You may accept. “For example,” recalls Khona, “when I went on a girls trip last year we ended up meeting a bunch of guys in Vegas. Most of the girls were already taken and many of the guys were, but they graciously offered to pay for our drinks. They didn’t expect anything from us, nor us from them. They were just being chivalrous and it was all in good fun.”

Related: What Your Drink Says About You On A Date

3. If you’re having an actual conversation
If you’re talking to a guy that you’re not particularly attracted to but you’re also not in a hurry to get away and the conversation is flowing naturally and he’s not blatantly hitting on you and he offers to buy you a drink, it’s okay to accept. Then, if you keep talking and drinking and you’re still not attracted to him, but you think you might have made a friend? You can offer to buy the next one.

Related: 20 Questions We Wish We Could Ask On A First Date (But Never Actually Would)

When It’s Not Okay:

1. If he’s obviously hitting on you
If some poor chump rolls up on you and says, “Has anyone ever told you you’ve got gorgeous hair? I’m Steve,” the drink that he offers to buy you is an invitation to his semi-furnished van, not just a friendly gesture. Though it’s tempting to just fleece this tool for all the drinks he’s worth, you probably shouldn’t. “If the dude is blatantly trying to pick you up, then NO,” cautions Khona, “Using people is not cool and it’s bad karma.”

Related: 7 Types of Guys Who Won’t Make You Happy

2. If he’s shy
If a guy is physically shaking in your presence and just barely manages to stammer “D-drink?” you should just let him down easy. Accepting the drink, then wordlessly returning to your table could put a guy like this off dating forever.

3. If he’s a creep
“If you think he’s going to roofie you, I would say definitely not,” cautions Khona, “Or if he’s just generally gross or looks like a serial killer.” In other words, keep your head on straight and it won’t end up in some guy’s freezer.

Rachel Khona lives and writes in Brooklyn, NY. Do yourself a favor and follow her on Twitter and Facebook.


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