so there's this guy (named R) in a club I'm in at my college. he's a sports journalist and seems like a nice, well spoken guy, just seems to be a bit... Show More
Most Helpful Opinion
He probably feels the same way you do. The only way to deal with a shy person is to take the initiative, because the shy person won't; that's the definition of being shy.
When you've got TWO shy people, like him and you, then you have an even bigger problem, because there's no one who is naturally going to take the initiative. Very often, two shy people who like each other never get together, because neither one will make enough of a *sustained* effort to get past that initial awkward stage where neither believes that someone else actually likes them.
Your roommate was playing wingman and got the ice broken for the both of you, but you both failed to keep things rolling. If you want this to have any chance of working, YOU are going to have to start initiating, and soothing HIS fears, so that he believes that you are actually interested in him. Once he is convinced, he will probably take over from there, as he gets more comfortable with you, but you've GOT to get some momentum going, and he's clearly too shy to do that himself, even though it sounds like he wants it as much as you do.