How to get to know a shy bookish person better

Anu asks: If guys are so shy that they might shiver in front of you while having an in-person conversation, and they are really bad at texting, how can a girl even try for him? The girl has already made the first move. He shows signs of liking her, but the problem is that he is a hardcore book nerd. What to do next?

Hi Anu –


I have a few pieces on my website about how to approach shy guys, but as you say, you’ve already done that.  And it’s worked.


So what next?  Well, I have a few thoughts, but I can’t guarantee any of them; they’re just ideas.


– if he’s a “hardcore book nerd,” get him talking about books.  Are you a reader too?  Maybe you could ask him about his favorite books, and read one of them.  (Or just see what he’s carrying around and try that too, though there’s then no way of knowing if he particularly likes it)


– talk to him about what YOU’RE interested in.  One thing about “book-nerds,” they spend tons of time experiencing what someone else (the author) finds interesting!  So he’s likely to be interested in what interests you – if you can sell it the right way.  For example, my human friend Handsome grew up at a school where there was lots of attention on American Football.  He didn’t like it much, and was particularly bored with the way people talked about it.  Then a few years ago, a friend told him about a TV series about high school football.  “Why would I want to watch that?!” he asked.  The person gave him very good arguments why, he watched it, loved it, and we saw every episode of the series.  (I mainly liked that the coach’s wife had my hair color!)


– help him with something he’s having trouble with at school.  If he’s so shy, maybe you can help him with something he’s too shy about.


– ask him to help you with something!  Does he know a lot about history, or science, or Harry Potter?  Figure out a reason to ask him about what he’s good at.  I’m sure he’ll love being able to help; shy guys love feeling valuable!


– and biggest of all… ASK HIM OUT!  Do you have school dances?  Ask him to one.  He’s so shy, he’ll likely really appreciate you having the courage to do that!  Or ask him to go to a school play with you – book nerds usually love plays!


The important thing here is that you know he likes you.  Maybe not liiiiiiiiiiiiiikes you just yet, but at least likes you.  That’s great!  Use that.  He will love getting pulled out of his little world by someone he likes; we all do.



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