You might say something like: “I read your blog post last night about history class and it was so funny and well written! I can’t wait to read your next one. ”[2] X Research source Be careful not to overdo the effusiveness, which could make you seem fake.
Not all guys know how to fix things. Make sure that he’s knowledgeable about what you’re asking of him or else your plan may backfire and he might up feeling embarrassed.
“How did you get interested in carpentry?” “What brought you to live in San Francisco?”
Make sure to show interest in him and not just his role or activities. Hobbies and interests are good, neutral places to start, but when you’re both ready, be sure to look deeper.
Ask permission first, and make sure he’s open to that sort of attention and affection. Try lightly and briefly touching the outside of his arm to communicate assurance while you’re having a conversation with him. If you aren’t interested in him romantically, be cautious with physical contact. Giving him frequent hugs, for example, may seem friendly to you but he may interpret it as a romantic gesture.
If you give him a nickname, make sure that it’s positive and that he’s comfortable with being called that name.
It is best to consider that not only is this an investment on your part, but the shy guy must also put in a fair amount of invested work on their own as well. The most you can realistically hope for is that you can slowly chip away the shell that the shy guy has encased himself in. Be understanding and practice patience and acceptance.
He may seem awkward around you at first. Be persistent and compassionate.