Questions to Ask a Guy — Free Conversation Cards Online

What's something you're good at that never comes up?

What did you want to be at eleven years old?

What's the last thing you got properly into?

Two days, nothing owed to anyone — what happens?

What's your most-worn item of clothing?

What sport or team could you talk about for an hour?

What's the best thing you've eaten this year?

What did your friends and you do for fun at seventeen?

What's a film you'd defend against anyone?

What's your worst habit that you're not planning to fix?

What's the last thing that made you laugh out loud alone?

What's the furthest you've travelled and why there?

What's your idea of a good Friday night now versus five years ago?

What are you saving up for?

What's the oddest way you've earned money?

What's something you own that you'd never replace?

What's a skill you'd learn if it took a week?

What music did you pretend not to like?

What's your go-to order anywhere?

What would you do with an extra hour every day?

What are you actually working towards?

What's something you've changed your mind about?

Who taught you the most about being a man, and what did they get wrong?

What do you do when things go badly?

What gamble of yours actually worked out?

What's the worst stretch you've come out the other side of?

What kind of friendships do you keep, and why those?

What do people get wrong about you?

Where are you when you stop performing?

What's something you're not good at that bothers you?

What did you learn from your last relationship?

What makes you relax around someone new?

Which choice sent your life down a different road?

What are you proud of that isn't obvious?

What do you do when you can't fix something?

Who do you talk to when you're struggling?

Where's your line that nobody gets to move?

What's something you've had to unlearn?

What do you want your life to look like at fifty?

What's the last thing that genuinely moved you?