First date with a shy guy?

i took initiative and asked him out. he said yes, hence the question...i know him well enough to say he's laid back, but I am completely clueless as to what to do. he doesn't talk much unless it's to ask me questions about myself. I don't want to talk about myself the whole night, but I don't want to make him uncomfortable by interrogating him either, so what's a fun way to hang out with enough distraction to keep us both balanced verbally, but not so distracted that we don't get to know each other... I live in the city, by the way, so there's more than just a mall and a diner lol.

any advice would be lovely :)


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Most Helpful Guy

  • Ok, I think you should not be afraid to ask him questions, because if he is at all serious about the date, he won't mind.

    Also, you asking him questions shows you're interested...a good thing!

    Just remember the first date topics to avoid...politics, religion, the size of his bank account, and former lovers. I think that's mainly it. If one of these things happens to come up, you don't have to completely avoid it, but it's best not to try to bring it up.

    A good way to ask questions is to share a little bit about yourself, and then ask for his opinion or use that to lead into a question about him. That way it's not like you're interrogating him, but you're talking about yourself and asking questions at the same time.

    Feel free to talk about whatever you see around you. Since you're in a city, there should be plenty of things to talk about. You might consider just taking a random walk with him with no predefined destination...and that way, at every intersection, there's the decision of which way to turn, which is something to balance the conversation if you two are struggling to find things to talk about.

    Also, try talking about people you know (and if there's people you both know that's even better). While I don't condone gossip, sometimes it's easier to talk about other people.

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What Guys Said 2

  • I am like this guy. And you should try to ask questions about him, it's easier if you're both asking questions. Plus it'll be easier to find something in common. As I am shy, I usually don't like having to start the conversation, but if you can start something off he'll most likely get more comfortable with you and start talking more.

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  • i don't really know why shy guyz even get on a date ,i mean they're boring and this whole relationship is gonna be boring as f***! go for any guy but the shy type , my advice to you ;)

    peace.

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What Girls Said 2

  • I've dated a shy guy before. 4 months it lasted. I hated having to initiate everything. That's why we broke up haha, but besides that...

    I think the best place to take him out would be at a restaraunt with lots of people. Then he'll be forced to speak up ha! Good luck.

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    • Ditto. Dated a shy guy for about 5 months and couldn't stand it any longer. He was a good guy, but I was exhausted. We stayed shut up in my apartment most of the time because he wouldn't speak more than a few words at social events or with my friends. When I met his parents for the first time, he said one sentence and then made me carry on by myself for the rest of the time. I'm stressed just thinking about it.

  • Ugh seems like a headache to me lol dates are hard enough without having to coax a supposed "man" out of his shell. Sorry I won't be much help.

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