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Depending on what kinds of get-togethers he likes, this question can have some wildly different answers.
Cool! guy friend wants something they are deed to get an interesting conversation started, and so some of the questions are a bit off the beaten track.
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And it can also tell you a lot about what he thinks success is.
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Weird questions to ask a guy — Yup, these questions will probably get you a strange look from the guy you are asking. Years after the movie came. What fictional character is portrayed as a hero but is actually more like a villain?
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Happy Birthday to a great guy! What are some fun euphemisms for everyday activities?
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To keep the conversation going, keep switching out the celebrity. Or perhaps a hero whose actions bring about horrible unintended consequences.
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And yes, I know that sappy stuff makes you cringe. But I think this is a more interesting way to ask the question.