Tips for dating a shy man
So let your guy know that you are here to help him overcome his shyness (if that’s something he would like). It doesn’t make your boyfriend any less cool or loving or amazing. If it’s something he wasn’t even aware of before he met you, explain it to him.
If being emotionally and mentally available for him will help him overcome chronic shyness that he’s struggled with for years, then so be it. So don’t keep gnawing at his conscience with the fact that he’s really shy. If it’s something he knows about and likes about himself – accept him!
Shy guys can be perplexing— they may not openly let you know they like you or ask you out, so you'll have to be willing to make the first move in order to date them.
Once you've broken the ice, work your magic to get closer to a shy guy.
A confident man can comfortably make eye contact with a cute stranger, offer a friendly smile, and strike up a casual conversation without seeming phony or full of himself.
If the idea of approaching a woman you don’t know feels overwhelming, take it slow.
Practice making and maintaining eye contact with a member of the opposite sex every day for a week.
If your beliefs about dating have been largely negative, it’s time to retrain your brain. Let go of any dating disappointments and other drama you’ve experienced.
Believe that future dating success IS possible for you.