I like this shy guy and I'm scared he won't ask me out because he's scared or something. How could I get a guy to feel comfortable to ask?
Most Helpful Guy
I take it you're either in middle school or high school. You're also not giving us enough information about the relationships between you two. Are you guys cool with talking to each other at least? Are you guy even friends? How often do you see each other (even if it's from a distance). If you're absolutely certain he's shy or really shy, he will NOT ask you out, ever. You're the one that has to do the approach.
There are number of reasons why he's scared. the most popular one is that he's scared of getting judged by the peers if you reject him from going out and another big reason if you're still under 18 is that he's afraid that you don't even like him at all or at least in that way.
If you like this guy, you have to tell him to help you with something. Shy guys LOVE helping a girl out that he likes. I'm not kidding. They are more prone to helping you out than guys who are confident with girls. If he really likes you, he'll do anything to help you out. I don't care what it is.
Don't do something like if you are sitting next to each other and if a pen is in your reach and you ask him to get it for you. That'll just make him feel like he's your slave (but not in the really bad degree).
Another approach is for you to do is to find something he's good at or at least observe that. Then TELL (not ask) to help you with it. Whether it be school work or something else.
In the end, you have to get him to help you with something. GL with your guy.0