Coming from a guy, I know it can kind of suck. When people just stop talking and you're not sure what to say...I have that problem a lot. I think finding serious common ground is the best: maybe you guys both have a strange obsession with jelly, or maybe you both watch anime every single second of your spare time. I don't know. If not, you can always try and get to know him and talk about what he likes, what is family is like. Seriously though, I probably won't be much help: I have the same issue when talking to girls.

I've never had this problem because I talk way too much! x)

My honest opinion is that if you're a little shy or not super talkative, you will have to find a person who knows how to bring out a more talkative side out of you. Eventually you'll meet the right one, but until then... if someone can't hold your interest in a conversation and do the work to bring up good subjects, they're the ones missing out on you!

Best advice in the world there from Lassen