Date Night Questions

Conversation Starters

Pick a question. See where it takes you.

A few questions to start with

A small taste of our date night questions, grouped by mood — flirty, funny, romantic, random, deep, and hypothetical.

Flirty

  • What's the first thing you actually noticed about me?
  • What's a trait you find attractive that you have absolutely no business finding attractive?

Funny

  • What's a completely normal thing that people do that irrationally annoys you?
  • What's the worst text you've ever sent to the wrong person?

Romantic

  • What's something that instantly makes a moment feel romantic to you?
  • What's a small gesture that would make you feel really loved?

Random

  • What's something you could talk about for way longer than anyone expects?
  • What's a completely random opinion you feel surprisingly strongly about?

Deep

  • What's something you've changed your mind about as you've gotten older?
  • What's something you're proud of that nobody ever asks you about?

Hypothetical

  • If we could disappear for 24 hours and go anywhere, where would we go?
  • If I gave you a plane ticket and said "pack one bag," where are we going?

How to use these date night questions

  1. Pick a mood, or keep it on All

    Choose flirty, funny, romantic, random, deep, or hypothetical, depending on the night.

  2. Take turns with Next

    Read the question out loud and both answer it. When you're ready, hit Next or Shuffle for another.

  3. Search for a topic

    Looking for something specific? Search the deck for a word like “love” or “first”.

  4. Save the good ones

    Tap the heart to keep a question for another night. Favorites stay in this browser.

The six moods

Every one of the 60 questions is tagged with at least one mood, and some with more than one. Filter by the kind of evening you're having.

  • Flirty · 11 questions

    For when you want a little spark. Good early in the evening, or early in the relationship.

  • Funny · 17 questions

    Low stakes, lots of laughing. A good way to start if you're both tired.

  • Romantic · 24 questions

    About what makes each of you feel loved, and the moments you'd like more of.

  • Random · 23 questions

    Questions you'd never think to ask. Good for breaking a routine.

  • Deep · 18 questions

    For later in the evening, when you've got time to actually talk something through.

  • Hypothetical · 21 questions

    What-ifs and would-you-rathers. Easy to answer, often surprisingly revealing.

Setting up the evening

  • Start light

    Open with something funny or random. The deeper questions land better once you're both relaxed.

  • Phones down, except for this one

    Keep one phone out for the deck and put the rest away. It's easier to listen when nothing's buzzing.

  • Follow the tangents

    If one question turns into twenty minutes of stories, that's a good night. There's no list to finish.

  • Save heavy topics for another time

    Date night is for connecting, not for sorting out disagreements. Note anything big and come back to it.

Long-distance date nights

The deck works in any browser, so you can both open this page and talk it through on a call. One of you picks the question, you both answer out loud. If you'd rather answer on your own first and compare, try the getting to know each other questions, which you each answer separately before seeing both sets of answers.

Questions people ask