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Breaking the ice with a guy you like can sometimes be challenging. It can also be tough to break past the typical flirty banter and really get to know each other. And talking about the same old things can get tedious. A little while back I started keeping a list of cool and interesting questions to ask a guy in an attempt to avoid awkward silences and generic conversation. And this is something important to keep in mind about conversations in general. The best approach is to go in without an image of them, and without wanting to seem a certain way in their eyes.

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When you're trying to get to know someone new, you can only text "what's up" so many times. Most people don't come right out and spill their deepest secrets. Well, that's what the 21 Questions game is for!

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These sneaky questions will help reveal the stuff you can't tell on the surface—a person's hopes, dreams, and values. And, just in case 21 questions isn't enough to get to know each other, we've included 55 so you will never run out of things to ask.

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The rules are really simple. To play, just choose questions from the list and ask your crush them one at a time.

First date

The game can be one-sided, or you can play too and the two of you can ask each other the questions back and forth. What's the most embarrassing thing you've ever done to get a crush's attention? If you go to a restaurant and have terrible service, is it ever OK not to tip?

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Would you rather leave your hometown and never be able to return again, or stay in your hometown but never be able to leave? If you could only hear one song for the rest of your life, what would it be?

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What to be mindful of when asking questions

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