Questions I can ask my crush? He's also shy?

So we're talking, and I can see he is trying to overcome his shyness..
Earlier he would very rarely text first (which meant we weren't talking at all) and once I texted him first it was like a switch turned in his head, lol
Now he's texting me every day :)

But there's a huge BUT...
He's still kind of hesitating to ask some things and it makes our convos hard sometimes. And when he does, it feels like Im always talking, I want to encourage him to open up more.

What can I ask him, without being too obnoxious (since I dont want to scare him away)? Could you give me some examples?
I've never dealt with a shy guy before, most guys were really assertive when talking to me.


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What Guys Said 2

  • Keep encouraging him to talk, text him first... do watever it takes... because guys like these are keepers... they will never leave u...
    Once he is comfortable enough with u... he will himself start initiating...

    • Exactly, somehow it feels like he's worth it!

    • I can give u in writing... he is a KEEPER...
      and always beware of the smooth talkers, who smoothly talk to women... they are the actual players, however a guy who is shy obviously doesn't have experience with women and he will be a one woman man... dont leave him ever...

  • You can ask him about his family, friends, school/work. Encourage him to tell you his past experiences: travelling, going to the zoo, theme parks, how was it to take driving lessons, video games that he plays, sports.
    Talk about food, talk about drinks, talk about movies, songs, tv shows.

    • talk about how you think of him during the day, and why you thought of him in that particular moment

    • Show All
    • Good, talk about vegan recipes.

    • We got that covered pretty much, haha

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