Issue #27: How to start a great conversation no matter whom you're with

23 questions to ask new, old, and best friends

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Oct 26, 2023

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“What expectations were your families bringing to your wedding?” I asked. I’d met the person sitting next to me on the shuttle bus about five minutes earlier. Clearly, we’d skipped the small talk.

When we got off the bus, I said something to that effect. He smiled. “I hate small talk. This was much better.”

I think most of us resent the fluffy, meaningless, let’s be honest, boring conversations we have with people we don’t know well, haven’t seen in a while, or typically don’t go deep with. But it’s so hard to escape. How do you go from “and have you always lived in Boston?” to “tell me about your hometown” or even, yes, “what’s your perspective on the ritual of marriage?”

For me, it comes down to having the right questions up my sleeve. A great question can transform a long car ride, first double date, even arranged seating at a wedding — provoking laughter, silliness, intimacy, or all of the above.

How do you go from “and have you always lived in Boston?” to “tell me about your hometown” or even, yes, “what’s your perspective on the ritual of marriage?”

Here are some of my favorites, organized by how well you know the people you’re asking. This roughly corresponds to the intimacy of the question, but feel free to mix and match.

Acquaintances:

If you had a two-way portal you could use anytime that would deliver you to any place on Earth, where would it go? (You cannot sell access to this portal but your friends and family could use it with you.)
What are your favorite and least favorite nicknames to be called?
What book/movie should people have to read/watch to graduate from high school? College?
If you could have an incredible beach, mountain, or city view, what would you choose and why?
You have 60 minutes more in your day than everyone else (even Beyonce.) How do you use it?
What’s the most impressive thing you can cook?

New friends:

What internet rabbit hole have you gone down recently?
What did your parents almost name you?
How often should a pair of jeans be washed?
Which celebrity do people most often tell you that you look like?
Is “thanks in advance” passive-aggressive?
What’s the worst karaoke song and why? Best?

Established friends:

Who on the internet do you stalk?
What’s your guilty pleasure music?
What’s something in your wardrobe you bought randomly that’s since become a keystone piece?
What’s been your favorite gift to give? Receive?
What was your childhood obsession?
Would you rather have your credit card statements or text messages made public?

Great/best friends:

If you could relive a single year in your life — experiencing it again without changing your future — which year would it be and why?
What do you think about when you’re falling asleep?
What are you the best at?
What’s the pettiest reason you’ve been turned off by someone? (Romantically or platonically.)
What was your favorite playground as a kid?

Sam and I have a routine — as many couples do — where we’ll take our question of the month on a tour. When the first silence of a conversation pools, we’ll make eye contact, then one of us will say, “So, we need your opinion on something…” or, “We’ve been asking people this question…” (This routine works just as well as a solo act.)

The more answers you collect, the more layered the conversation becomes. “Yeah, so and so said the same thing!” Or “That’s so interesting, you’re the first person to think of XYZ.” You can easily spend a happy half hour on the initial question and a few more on the detours the conversation inevitably goes down.

Tell me your reliable conversation starters in the comments.