How his day went His past experiences (like where he lived as a kid, what he liked doing, who’s important to him in his family) His hobbies His favorite activities His favorite books, movies or music.
Play devil’s advocate. Present a counterpoint to whatever your boyfriend says, so that he’s forced to re-evaluate his choice. Make it clear that you’re just trying to make the conversation more interesting––you’re not actually trying to disagree at every turn. Some more hypothetical questions to ask: “What keeps you awake at night?” “If you could live your life to this point over again, what would you do differently?” and “What couldn’t you live without?” (or, “If you could only keep 10 things, what would they be?”.
Nostalgia is a good bet here. Ask him about his first memory, his first day at school, his first toy and his first birthday party that he can remember. It’s a great way to get to know about the things that matter to him and what he was like when he was a child.
Tell him a few jokes that are quite funny and laugh along with him (provided he has a good sense of humor).
Where you want to go to school What you want to study Where you want to live Where you want to travel Possible hobbies What job you want to have.
Chess Checkers Scrabble Speed Egyptian Rat Screw Sorry
If it’s early in your relationship and you encounter a lot of silences, try to keep conversations to no more than an hour at first. Talking too much can make even a fresh relationship seem stale and boring. Let him know you’re still there. Small talk can turn into silence very quickly.
