How to go about dating a guy who's very shy and unsure of himself and you're just as bad?

I'm very shy myself, but I feel awful because he seems to be struggling... big time. It's like a vicious cycle.. mean, he's so nervous and shy around me that I took it as disinterest, which made me even more anxious and shy (might have something to do with the fact that his ex chated on him). We've been dating for a little over a month now, and he surprised me last week by being extremely affectionate when on all of our other dates he has seemed almost too terrified to touch me. His burst of affection was all it took to break the ice for me, and even though I'm very reserved and cautious myself, I followed his lead and freaking went all-out with kissing and cuddling him after that, and he was even playful in a childish way. He seemed more comfortable with me after that, and invited me to to sleep over at his house in a couple weeks since he'll have the house to himself. He also always uses "we" when making plans and remembers the littlest details about me, if that means anything.

I want him to know that I like him by showing more initiative.. but I don't know what kind of dates to ask him on or how to act without overwhelming him or anything. I mean, I've asked him what he likes to do for fun, but he said he doesn't have time for fun since he's busy with his education and work and such, so he usually just spends his free time relaxing at home and watching movies or reading. It's just hard because I don't want to interrogate him but he doesn't really talk about himself much. I thought I should show I trust him by opening up to him more about myself, but I don't want to come across as self-absorbed... I don't want to make him uncomfortable by prying if he isn't ready.


Most Helpful Guy

  • first of all have u ever been in a reltionship before? i ask coz it seems he has some xperience wid relationships since u mentioned he has an X.

    anyway... if that's so he knows how he'll move and as it seems he already started openin up by being more affectionate. so sooner or later he'll start talkin about himself... but u can also say a few things about yerself as well... u won't pass as self-absorbed. after all it seems he likes u

    • I was in a 3 year relationship... but it wasn't a healthy one, so I don't have much to go from.

    • Show All
    • Thank you.. We shall see :)

    • u r welcome and thanks for MHO :)

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