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So in celebration of the familiar and unexpected about each other, this date night invites you and your sweetie to get acquainted in a fun new way – with your very own…. 32. What would be your chosen superpower? You might also like: First date questions. 33. What’s the weirdest thing you have ever done that makes you feel embarrassed to talk about? 34. Are you a hopeless romantic, or are you a tough nut to crack? 35. What’s the funniest injury you have ever been to the hospital with?These 250 interesting first date questions for guys and girls will get both people talking and laughing! First dates can get pretty exciting, especially when you feel that special spark as soon as ...Asking the right ice breaker questions for dating can help ease the awkwardness and ensure that future connections are made. In other words, we are interviewing each other while out on a date. It’s about discovering who we are, what we want, and whether we’re compatible or not. 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