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Ask about topics that you know he finds interesting. People in general are most comfortable talking about themselves or their interests. Why? Because it's something they know pretty well and have mulled over. Here are some ideas for things to ask about: 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.
Talk about hypothetical situations. Would you rather be blind or deaf? Would you choose subsisting solely on spinach over listening to Christmas songs for 8 hours a day for the rest of your life? Try to come up with interesting, funny or complicated situations, and ask your boyfriend what he'd prefer. When he answers, ask him to defend his choice. 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?".
Ask him to tell you something you don't know. It can be something about himself, or a fact you don't know. Whatever it is, you're sure to learn something. If you want to be more specific, ask him to tell you something new about one of his hobbies. 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.
Ask him things that are quirky. This can lead to fun, entertaining questions when you're both already in a good mood. Questions like: "Do you still believe in Santa?", "If you had to choose between the TV and the Internet, which one would you get rid of?" and "If there were no clocks, what do you think life would be like?". Keep the conversation light and amusing, no answer is the wrong one! Tell him a few jokes that are quite funny and laugh along with him (provided he has a good sense of humor).
Be complimentary. All of us love to be complimented and recognized for our actions. Tell him how, and why, you loved a particular date. For an example you might say, "I loved when you took me out to dinner. It was such a beautiful restaurant that it made me feel extra special."
Discuss the future. Talk about the things you'd like to do someday––maybe you want to visit Crete, star in a play, write a novel, or live on a boat. Ask about what he's dreamed of doing. Here are some possible topics: 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.
Play a game. It could be a board game, online game, or video game––whatever you choose. If you're competing against each other, you can gently trash talk and rib your boyfriend. If you're playing on the same team, you can discuss strategy and gameplay. Try these classics: Chess Checkers Scrabble Speed Egyptian Rat Screw Sorry
Listen actively. The art of talking with another person includes a lot of listening that encourages the other person to talk more. Show your boyfriend that you're genuinely interested in what he has to say by acknowledging the things he says, using affirmative statements and body language as he speaks and summarizing aspects of what he tells you so that he knows you've taken it on board. 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.
Stay informed. If you can find time to watch or read the news, you'll have more topics floating around your mind. Keep up on current events, funny clips of comedy shows, or viral internet stories. When the conversation lulls, ask your boyfriend if he's heard of what you read or saw recently. If he has, you two can talk about what you think. If not, now is the perfect time to tell him all about it.
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