What do you most like to do for fun?
We always ask people about work, but how they play is just as important to who they are.
Who is your favorite superhero (and why)?
This is a silly change up to throw in to keep the conversation lighthearted. This is a question that keeps working well even as you add more people into the conversation.
What makes you laugh?
Life just wouldn’t be the same without laughter. When you find out what makes someone laugh, you’ve taken a big step toward learning what makes their life fun.
What is the most interesting thing you learned recently?
In a way, this question is doing them a bit of a favor. By telling you about something they’ve learned, they lock in the lesson.
If you don’t mind sharing, what is your most embarrassing memory?
Another one that’s perfect for mealtimes. There’s something about sharing food that pairs well with funny stories. Hopefully their most embarrassing moment doesn’t involve bodily functions that might cause you to lose your appetite.
Do you have any secret dreams you rarely talk about but hope come true?
Everyone has a dream, but almost no one talks about it. If you want to get to know people on a deeper level, asking them about their dreams is a winning strategy.
What is your favorite dessert?
The great thing about dessert is that it makes no pretense of being concerned with your health. You eat dessert because it tastes good. Simple pleasures make for easy conversation topics.
What is the tastiest thing you know how to cook?
This can open the door to more conversation topics:
- Do you usually cook, or eat out?
- How confident are you in your cooking sills?
- Where did you learn how to cook?
If all restaurants and food chains were going out of business, and you had the chance to save five, who survives?
This is the most ridiculous question I’ve ever come up with, but it actually goes over really well. It seems like every time I ask it to one person in a group setting, someone else overhears and joins in to share their list.
Do you have something you are looking forward to?
This is great to get to know the person, but it also gives you a perfect follow-up question for the future: “How did that thing go that we talked about last time?”
What excites you right now?
To me, this is much better than “what do you do for a living?” (or for college students, “what are you studying?”). People might hate what they do for a living. What you want to know is what lights a fire in their belly. It might be work, or it might be something else.
What is a childhood memory you hope you never forget?
I went on an awesome weekend trip with some buddies. During dinner one night, I asked this question, and we all shared. It made for a memorable and fun conversation.
What is the best thing that happened to you this year?
If it’s early in the year, you might want to change the time frame to “last year” or “in the past year.” This is a great question because it gives them a chance to choose something that is important to them.
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