Most Helpful Guy
Just approach him normally say hi, talk about something the two of you have in common. Its less about what you say and how comfortable you make him feel. As a shy person you know how stressful social situations can be to us (a good conversation starter), just try a little empathy, when you are talking to someone you don't like pressure being put on you to be a 4 star entertainer, and I'm sure you don't like it when people seem bored or uncomfortable if there is a long pause.
Just make him feel like you enjoy spending time with him despite the fact his social skills may not be that good, that is the most important thing!
Most Helpful Girl
I'm in the same situation and i didn't know what to do. But i was in a vulnerable situation and he started a conversation with me, complimented me, and was really sweet. So if you smile, be where he is, and don’t act tough, he’ll probably feel more comfortable and might initiate conversation.