Fifteen questions in three gears, the two rules that keep them from turning into an interview, and why she'll answer things at 70 miles an hour that she won't answer across a table.
Two hours into a four-hour drive, the podcast ends and nobody reaches for another one. Neither of you says anything for a mile or two, and that's fine. It might also be the best conversation window either of you has had in weeks, and the only thing you've got loaded is "how's work."
The car is a better room for a real question than your kitchen table is, and it isn't close.
A few things are true in a car that aren't true in any room of your house.
You're side by side, so neither of you has to hold eye contact while saying something true. Nobody can get up to start the dishwasher. The drive has a clock on it, so an answer doesn't have to turn into a whole evening, which makes a big question cheaper to start. And you both have somewhere to put your eyes that isn't the other person's face.
People leave things unsaid because saying them means watching the other person hear it.
Angela C. wrote back about the questions I send out every week:
I always check them and ask them when we are alone driving somewhere. It's something we look forward to answering.
Where you ask a question matters about as much as which question you ask. That's the same argument behind Date Nights Dancing, my program: easy swing taught at home, fifteen minutes at a time, both of you learning the same moves from the first video on, because having something to do together beats a conversation you have to start cold.
You already own the car. It just needs better material than "how's work."
The famous set of 36 questions that Professor Arthur Aron and his colleagues built to accelerate intimacy between strangers is ordered on purpose. The cheap questions come first and buy permission for the expensive ones later. (There's a whole date night built on that set if you want the long version.)
So these are in three gears, five in each one. First hour, middle of the drive, last stretch. You won't get through all fifteen, and you're not supposed to. Two good ones make a good drive.
1. "What did you love about your first car?"
You're sitting in a car, so the subject is already there. You'll get the make, the color, the thing that never worked right, and then a story about who was in the passenger seat. If she gives you three words, tell her about yours and hand it back to her.
2. "What's the best trip you took before you met me?"
Before-you-met-me is a shelf that stops getting opened once the shared history gets long enough. If the answer is just a place name, ask who she was that year.
3. "If we didn't have to be anywhere, where would you want to pull off?"
This one is about the next forty miles instead of about her childhood, and it can end with the two of you standing at some overlook you'd have driven straight past. If she says she doesn't care, name two options and let her pick.
4. "What's the most endearing thing about me?"
Yes, you're fishing. Fish. Ask it with a grin so it's clearly a joke, then say nothing, because you may not guess the answer. Give her yours after, unprompted.
5. "What have you gotten good at this year that nobody's said anything about?"
This hands her credit without making it a compliment she has to deflect. If nothing comes to mind, answer for her: name one thing you've watched her get better at, then ask again.
6. "When did you know you wanted to be with me?"
The how-we-met story gets told at dinner parties. This isn't that one. It asks for the private moment she decided, which she may never have told anybody, including you. If she reaches for the obvious milestone, ask what happened the week before it.
7. "What has being with me taught you about love?"
It's a big question that goes down easy, and it only works if you answer it too, in about the same detail you asked for. Ask it, skip your own turn, and you're running an interview.
8. "What's the one thing about us we've never figured out?"
This is the closest thing to a live wire in the whole list, so ask it only if you can hear the answer without defending yourself. If the answer turns out to be about you, the correct next sentence is "tell me more about that," and then nothing.
9. "Other than me, who had the biggest hand in you turning out the way you did?"
In Power Questions, Andrew Sobel and Jerold Panas describe "How did you get started?" as "a question even the most celebrated, powerful, or wealthy person cannot resist." Point it at the people who built her instead of at her career and you get the same effect. Follow it with "what did they do, exactly?"
10. "Can you tell when I'm faking a smile?"
This is the rare one in this gear that's about you without being about your feelings. Expect a specific example, and expect it to be right. Then tell her the one you can spot in her.
11. "What do you think I need to hear right now?"
Most questions ask her to reveal something. This one asks her to give you something, and it tells her you think she knows you well enough to answer it. Whatever comes back, don't argue with it. "Thank you" covers it.
12. "What would you go back and tell yourself at twenty?"
She's talking about a version of herself she doesn't have to defend anymore, which is what makes it safe. It gets at regret without either of you having to use the word. The follow-up worth having: "what would you have refused to believe?"
13. "What are you most excited about in our life right now?"
Gear three isn't all heavy. Ask this one before the last two so the drive doesn't end on the heaviest note available. If nothing comes, that's information, and the next question is what she'd like to be excited about by this time next year.
14. "Is there something you've wanted for a long time that you've never told me?"
In Power Questions, Sobel and Panas write, "Absorbed by the details of our day-to-day lives, we are rarely allowed to dream." A car with two hours left on it is one of the few places a long-held want gets spoken at all. This isn't one to solve. See rule 1.
15. "If nothing had to stay the same, what would you want the next five years to look like?"
The closer, because it's the only one on the list that needs both of you and produces something you can act on Monday. Ask it with real road left, then answer it yourself in the same detail.
Rule 1: Don't fix it. In I Hear You, Michael S. Sorensen names one habit as by far the most common mistake people make: giving unsolicited advice or reassurance before you've acknowledged what the other person is feeling. It reads as a verdict that the feeling itself was wrong. In a car the fix reflex is worse than usual, because you've got nothing to do with your hands and no kitchen to walk into.
Sorensen gives two openers that solve it: "How can I help?" and "I have a few thoughts on that. May I share them?" Either one, asked before the advice, changes the whole exchange.
Rule 2: Don't fill the silence. In Power Questions, Sobel and Panas give the instruction plainly: "Don't fill in the silence." Three seconds of road noise after a real question isn't a failure. She may be deciding whether to give you the short answer or the true one, and every word you say in that gap makes the short one likelier.
When the answer does come back thin, the cheapest follow-up in the same book is "Can you tell me more?" Ask it often. It works on almost everything and it costs you no preparation at all.
Both rules are about the ten seconds after a question rather than the question itself. One more belongs with them: answer the one you just asked before you reach for the next one. Fifteen questions fired back to back is a deposition, and it won't take her long to spot the list.
I'd hold these rather than burn them at dinner tonight. They're built for a long stretch of road with nowhere either of you has to be.
Screenshot this page before you leave, or take the questions I send out every week and let them stack up in your inbox until the next drive. That's what The Spark is for. Dory and Ashley C. wrote in about where they use them:
I always use the questions for discussion. They are great for car rides or sitting on the front porch.
If you want material for the other slots too, there are dinner-table versions and last-ten-minutes-before-sleep versions, and a longer list of questions to ask your wife if you'd rather pick your own. More of that kind of thing lives in the ideas hub.
You don't need all fifteen. One good one, asked at mile 180 with the sun going down and nowhere to be, can do more for the two of you than a whole evening of catching up across a table.
And if the drive goes well and you get home wanting more of that, Date Nights Dancing is the same idea standing up: easy swing in your own living room, fifteen minutes at a time, both of you learning the same moves together from the first video on.
You're already the guy who thought to bring questions on a four-hour drive instead of another podcast. That part was yours before she said a word.
The Thursday reminder over 100,000 couples love: ideas and conversation starters that deepen love, laughter, and intimacy.
