ANSWERS: 8
  • Ask him who was his first best friend, and why did he like this person so much. Then see where it leads.
  • Who does he see as a role model and why?
  • My experience is that people especially guys do not like to be bombarded with questions. I would say just go out and have some fun and let the conversation proceed naturally. If a guy is having fun he will open up more. Don't ask about exes. Mood killer!
  • "So, what's the weirdest thing you did today?" If he answers something like, "I ate a tuna sandwich in bed..." you know, you're safe. If he answers, "I killed small animals just for fun..." RUN!
  • Men like to talk about their conquests (not sexually you perverts). So ask him about his job, any sports that he plays in, anything that has a defined answer that is something that he has already completed. If you ask an open ended question about the future, depending on the guy, you might get an odd answer because typically our moms ask us things like that. So if you stick to what he has already done and then use that information to ask your next questions you will be set. If he has a big answer with sports, ask him about his teammates and then what they would do for fun.
  • Ask him if he likes to have sex in public.
  • Ask him what he really dislikes. Being too specific might end up with you asking a question, that sounds odd, or lame to him, simply because he has no interest or experience with whatever you're asking about. Take me for example. I'm very athletic. I train regularly, and I'm at a high level of fitness. Football (soccer) is overwhelmingly the number one national sport in my country, and even more so in my city, but if a girl asked me about it, I'd be unimpressed, because I'm not a fan. If she asked me about my favourite book however, I'd be more impressed, but that's not what she expects. She is being too specific. Everybody dislikes something though, and mostly people like a moan now and again, and it can be funny.
  • Ask him who in his family he was closest to as a child.

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