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3 Questions To Ask A Guy On A Date (And 3 Questions To Avoid)

Our friends at Glamour very astutely pointed out recently that some of the questions the female contestants ask on The Bachelor are not particularly condusive to male conversation. ("When was the last time you cried?" was particularly hard to watch.)

Here are three of Glamour's suggestions for less awkward conversation topics, as well as three more questions we think you should avoid at all costs...

Go Ahead And Grill Them!

From Glamour:

1) "If you were to go on a game show and win a trip for two anywhere in the world, where would we be going?"
This question is great, because the answer will tell you a lot about the guy. Will he say something exotic, like Borneo? Then obviously he's adventurous, and relatively low-maintenance. Does he pick an English-speaking country? This might mean he likes to be in control, and hates being at a disadvantage when it comes to language. Does he want to go to a city? A beach? The wilderness? (Note: If he says something like an ashram or a quiet retreat, he might not be looking for a serious relationship just yet...)

2.)"If you ran into the President in the elevator what would you say to him?"
He'll either say something non-committal, try to make a joke, OR get really impassioned and political -- whichever way he responds, you'll definitely learn something about the guy's personality.

3.)"If you could have any super power—and you can’t say flying—what would it be?"
How cool is your guy? Is he "I'd be invisible" cool? Or is he "Zach Morris Time Out" cool, which is obviously way, way, cooler?

But never ever ask...

1. "So what do you look for in a girlfriend/what kind of girls do you usually date?"
No, no. Do not ask this. What if he lists qualities which you don't have? That's awkward. What if he lists qualities you DO have? That's also awkward!

2. "So are you really _____, or what?"
Basically, any adjective you can fill the blank with is bad. "Smart" after hearing he's gone to an Ivy League College. "Rich" if you hear he lives in a certain neighborhood, or likes a certain restaurant. "Jersey" if he says he grew up in Jersey. Any generalization that you can make from spending an hour with someone is usually not one the other person is interested in hearing. It's embarrassing, or offensive, and people usually won't know how to respond. Move on!

3. And on later dates, avoid fishing questions.
Guys (and girls!) are attracted to confidence, and questions that fish for compliments are usually far more transparent than the asker thinks -- anything along the lines of "What do you like about me?", "Do you think she's hot? Hotter than I am?" or "If I were in a horrible disfiguring accident, would you still date me?" Really, any "test" of a guy's devotion makes him feel annoyed and trapped. Take a deep breath. Remember he's out with you because he likes you. And relax.


More Like This:
10 Things You Should Know After A First Date
20 Questions We Wish We Could Ask On A First Date

The Date Report is the companion blog to, a dating site that makes it fun and easy to go on awesome dates. How it works: 1) Invent fun dates. 2) Ask people out. 3) Do something awesome, together. Sign up for free here. Don't forget to join us on Twitter and Facebook -- and download our brand-new app here!


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