So this guy who sits in front of me in history thinks I'm cute (according to his best friend) but the problem is that he's really shy. Being the awkward person that I am, I have no idea how to start a conversation with him casually. Help?
Most Helpful Guy
From a shy guy,
-Try to find common ground and talk about it, and if he likes something you don't then do not look down on him for it, even if its a "deal breaker" for you. If you're open to giving it a try it might be fun for both of you and let him open up. His friend may be a wealth of information for discussion. Maybe studying or working on one of your assignments together, ask him if he can help you out. It might be easier for him to say yes to that then entering an open situation like study group or coffee. He might feel good about tutoring you as it would create a framework for the situation for you to talk to each other.
-If you know his best friend, see if he will be your wingman. See if he will double with you and your friend in doing something he(or both of you like). I opened up around people I was comfortable with in situations I was comfortable; for example, I never liked being shoulder to shoulder in a bar when first meeting someone.
-You may not end up together so if it turns out your not interested, try and go easy on him but make it clear.
-You might have to be patient, a little alcohol never hurt anyone either.