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We all know how happy guys can be when they get to tell stories of their old days! These 30 fun questions to ask your boyfriend will get him thinking about a simpler time, laughing about the things he used to do, or even remembering the things that he felt the first time he laid eyes on you. The key is to keep it light and to have fun with it. Instead, you want to elicit a lighthearted, non-agenda response. What type of friendships did he have? Every superhero has their own cool thing.