Dating a shy boy
Waldon agrees that you should take it slow and suggests “low-key interactions such as a daytime study date or tutoring session.” It can be difficult for a shy guy to ask out a girl on an official date, so asking your shy guy to casually hang out clues him in on your interest so he can feel confident to take your interaction to the next level.
Greif says that another great way to get to know a shy guy is to participate in activities that interest you both.
How to Get His Attention Greif, Jasbina Ahluwalia, founder and CEO of successful matchmaking service Intersections Match, and psychotherapist Mary Waldon all agree that the number one tip for trying to date a shy guy is to take initiative!
Whether this means initiating eye contact, a conversation or a date, all of our experts stressed the importance of taking that first step.
Unlike more outgoing guys, shy guys might need a confidence-boosting signal from you to give him the courage to make a move.
Even if the shy guy doesn’t return your gaze, Ahluwalia says it doesn’t mean he doesn’t like you.
Once again, you help take the pressure off him because you’re the one who initiated the interaction.
This does mean they can be more difficult to ‘work out’ but it also means they are often far more worth the effort.
Breaking down the initial barriers are always the most difficult, don’t take their shyness personally or as a sign of disinterest. If you have mutual friends then take advantage of that, do some group activities where you can slowly get to know each other in a relaxed setting eg. Alternatively a great way to start a conversation is over social media, your shy man will feel less vulnerable and therefore more willing to chat.
How to Chat Him Up After you walk over and make that initial contact, Ahluwalia says that “providing a warm and inviting opening” is the best way to help a shy guy engage you in conversation.
“Don't worry if you continue to be more [talkative] than him as you develop your relationship,” she says.