Talk about his embarrasing moments and then it starts a long conversation and he will ask you yours it ok I have tried it.
How Can I Start A Conversation With My Boyfriend As He's Very Quiet? It's Our First Day Going Out.
Start talking about random stuff like sports, movies, or politics. Find something that he'll like. Who knows, you could probably find something you both like.
Well find a topic that he is interested also... Or ask him what sports is he into.... Maybe you have the same likes and dislikes..
Well, you would start by staying, hi/hey/hello or what ever, then go from there talk about sports foods family pets or absolutely anything, see were the conversation takes you!!
All you have to do is ask the guy a question about something related to a topic you want to talk about. Most likely he'll immediately start a long conversation with you. If he doesn't, that just means he is scared to death of saying anything wrong, I'm a guy, I know.