First-date questions that are fun to answer

A first date is two people trying to relax while also paying very close attention. The questions that help are the ones that are easy to answer and fun to hear: no right answer, no wrong one, and a decent chance of a story.

These come from Sweet, the first of seven levels in Kindling, our card game for couples. They work just as well without the game: on a first date, a third date, or any night you’d like to laugh more than you talk. The full list is below, in the order the game deals them, from lightest to boldest.

What makes a good first-date question

The best ones have three things in common.

• They’re easy to answer in a sentence and fun to answer in a paragraph. “If the two of you were in a movie, what genre would it be?” works whether your date says “romcom” or describes the heist film they’ve been casting in their head.
• They’re about opinions and preferences, not credentials. Asking what someone does for work is fine. You’ll learn more from the completely unimportant hill they will absolutely die on.
• You’d happily answer them yourself. If a question would feel strange to answer, it’ll feel strange to be asked. A first date should feel like trading stories, not filling in a form.

When to ask them

Not all at once, and not from a list held under the table. A few moments work especially well.

• The first lull. Once you’ve ordered and the small talk has run its course, a playful question resets the mood without any fuss.
• On the move. Side-by-side conversations are easier than face-to-face ones. Silly hypotheticals suit the walk to the next place.
• As a game, out loud. If you both like games, say so: “Want to do some ridiculous questions?” Naming it takes the pressure off, because now you’re playing, not interviewing. You can also open Kindling on one phone and take turns.

One question every few minutes is plenty. Let the good ones run as long as they want to.

How to follow up

The answer is the start of the conversation, not the end of it. Three follow-ups work on almost anything:

• “Wait, tell me more about that.”
• “What’s the story there?”
• “Has it always been that way?”

Then answer the question yourself, with about the same amount of detail. Matching each other’s openness is how two strangers become slightly less strange to each other. If they gave you a one-liner, give one back. If they told you a whole saga, it’s your turn for a story.

What to leave for later

Some topics are fine on date five and heavy on date one: past relationships in any detail, money, family conflict, health, and anything that asks someone to rate their own body. If your date brings one of them up, listen. Just don’t lead with it.

Skip questions you’d only ask to test someone, too. People can tell when a question is really a checkpoint, and it changes the mood from curious to careful.

And if they’d rather not answer something, that is an answer. Smile, move on, and don’t circle back. Every Kindling card can be passed with no reason and no penalty, and it’s a good rule for dates as well.

The Sweet questions

When you’re ready for more

Sweet is about having fun together. The next level, Curious, moves from what you like to what made you you: childhood memories, values, the things you’ve changed your mind about. When you’d like to go a little deeper, try our getting-to-know-you questions.