How do I get a date out of a shy guy?

Work woth a a guy who is very sweet, polite, handsome, and wait for it... SHY. Whenever I talk to him he always seems to laugh and follow up with something funny. I really want to ask him out but I don't want him to be frightened to where he doesn't feel comfortable talking to me anymore. He already starts conversations with awkwardness.


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What Guys Said 2

  • Ya wrestle'm down to the ground and say "YOU! Go out with me!"

    Or whatever...

  • First off, does he give any signs of interest?

    • That's just it... idk! He always smiling when he sees me and when he starts a conversation he starts it awkwardly. I don't know if it's because he is shy and trying to be nice, or if he is just trying to to get me to talk to him. I don't even know if him smiling everytime he sees me because i always make him laugh or if it's because he likes me. I mean i smile at people too but that doesn't mean i like them. I'm so used to liking guys who are straightforward.

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