Hypothetical questions work because nobody has to defend the answer. “What would you do if…” is pretend, so you two can be silly or oddly honest without it turning into a serious talk. Ask one, answer it yourself, then follow up on whatever surprised you.

The questions below are grouped by mood, from pure fun to the ones that say something about what each of you wants. If you want the full set, the questions for couples page has more.

Every question here comes from Lolo Cards - 5,200+ conversation cards for iPhone.

Why pretend questions work

“How was your day?” gets “fine.” “If you could swap lives with anyone for a day, who would it be?” gets a name and a story. The pretend frame lowers the stakes, giving the answer room to stay silly or turn honest.

There is some research behind the idea that doing something new together helps. In a set of studies by Arthur Aron and colleagues, couples who shared more exciting activities reported higher relationship satisfaction, and in lab experiments a short novel task together gave a bigger boost than a boring one. Two caveats: the survey part can’t tell which comes first, and the lab boost was short-term. A what-if question also differs from those tasks. I’d call it a cheap way to put something new into an ordinary evening, nothing more.

A second reason to try it: people tend to expect deeper talk to be more awkward than it turns out to be. In experiments with strangers, deeper conversations felt less awkward and more connecting than participants predicted. The participants were strangers, so treat that finding as a small clue rather than evidence about couples. You two may be more curious about each other than you assume.

Warm-up what-ifs

Start with questions that only need a quick, fun answer.

Illustration: a penguin and a partner penguin on a couch with a blanket, one holding a question card and laughing, as if time has frozen around them
Pick a pretend scenario and play along

Notice what happens after the first answer. Someone says “Paris,” and the next thing you know you’re planning where to get breakfast. Let it run.

Swap-and-switch questions

These ask you to step into your partner’s shoes, which is where the laughs and small surprises come from. The answer often shows how each of you sees the other’s day.

If your partner says something like “I’d finally sleep in,” don’t defend yourself. Ask what else. You’ll learn more from the second answer than the first.

Dinner guests and time travel

These show what each of you finds interesting, and none of them has a right answer.

The follow-up matters more than the pick. “Why them?” turns a trivia answer into something you can only learn from your partner.

Illustration: two penguins at a candlelit dinner table with an empty third chair, one penguin pointing at the chair and the other thinking
Who is the empty chair for?

The ones that say what you want

These sound light, but the answers tell you what each of you means by a good life: how you rest and what you’d keep.

Take your time with these. Answer in turn, and when your partner is done, say one thing about their answer that you didn’t know.

How to keep it light

A few habits keep the evening fun:

  1. Answer your own question. It turns an interview into a conversation.
  2. Skip the “gotcha.” If an answer makes you wonder about something, ask about the answer, not about what it “means.”
  3. Stop when it stops being fun. Three or four good questions beat twenty rushed ones.
  4. Pick a few and leave the rest for the next date night. There’s a longer list in deep late night conversation topics for when the mood turns quiet.

A silly question can lead to half an hour of laughing or open something real.

Sources