If you see him from across the room, hold eye contact for a little while and smile. Doing so may give him the courage to come over.
A shy guy will be more likely to engage with you one-on-one. If your friends are around, ask them to meet you later so you can talk in private. Then walk up to your shy guy with a huge smile and say “Hi. "
For example, if you both like Stranger Things, consider binge-watching the show or going to a convention together. You’re more likely to win him over if the interest is genuinely mutual. He’ll be able to tell if you’re pretending to like something just to get close to him.
Consider going to a movie for a first date with a shy guy, because there’s no pressure to talk or make face-to-face chit-chat. If he’s not the mushy type, resist the urge to plan a romantic candlelight dinner. Instead, go for something light-hearted and casual, so you can both be yourselves.
Over time, you might find that you enjoy the shared silences between you—it can be a relief to not always have to talk! Silence is perfectly okay and natural in relationships.
He might put on some headphones when you’re together to demonstrate a need to pull away. Or, he might grow quiet and withdrawn. If this happens, you might ask, “Why don’t I go in the other room and give you some space?” or “I think I’ll go hang out with my friends for a while. Call ya later, okay?”
Remember, just because you love your friends doesn’t mean your guy will. Give him some time to warm up to them instead of assuming that he’ll like them since he likes you.
For example, never say “Aww, you’re really shy!” or “You’re blushing!” Calling attention to his shyness will make him feel self-conscious and maybe make him not want to hang out with you.
