What makes a good first date question
A first date is two people trying to find out whether they want a second one, while also trying not to look like that is what they are doing. The questions that help are the ones that get a story, not a fact. “Where do you work?” gets one word. “What is the best part of your week usually?” gets a person.
- Easy to answer in half a minute. Nobody should need to think hard on a first date.
- Open, not yes or no. Start with what, which or when.
- About now, not the past. Childhood and old relationships can wait.
- Easy to turn around. If they ask it back, you should want to answer.
First date questions to start with
- What is something that made you laugh this week?
- What do you do on a day when nobody needs anything from you?
- Which trip do you still talk about?
- What is a skill you would learn if you had a free month?
- What is the best thing you have eaten recently?
- What are you looking forward to right now, big or small?
- What is something you are a bit of a nerd about?
- What is a film or series you would make me watch?
- Are you a planner, or do you decide on the day?
- What is your go-to order at a café?
- What did you want to be when you were small?
- What is a place in this city you think is underrated?
- Mornings or late nights?
- What is the last thing you changed your mind about?
- What is something people are often surprised to learn about you?
Questions for the second and third date
Once you both know you like each other, the questions can go a little further. Still nothing heavy, just more of who they are.
- Who in your life do you talk to most?
- What does a good weekend look like for you?
- What is something you are working towards at the moment?
- How do you like to be cheered up?
- What is a small thing that makes you feel looked after?
- Which friend would you call first with good news?
- What is something you have taught yourself?
- What is a habit of yours you are proud of?
- What is the most spontaneous thing you have done?
- What does your family do when everyone is together?
- What would your friends say you are like when you are tired?
- What is something you want to get better at this year?
When you are ready for more, our list of deep questions to ask your partner picks up where this one leaves off.
Questions to skip on a first date
- Anything about exes. It is rarely good news for either of you this early.
- Questions about money or what they earn. It reads as a test.
- Comments or questions about their body or looks. Keep compliments to things they chose, like a jacket or a book.
- “Where do you see this going?” Give it a few dates.
- Anything that sounds like a checklist. One question at a time, with real interest in the answer.
Games for new couples
A game can do something a question cannot: give you both a reason to laugh at the same time. You do not need to play for long. Five minutes is enough to break the first-date stiffness.
Before the date
Both of you take What’s your first-date style? on your own: eight questions to find out if you are the planner, the charmer, the romantic or the funny one. Share your results in your chat. It gives you something easy to tease each other about when you meet.
On the date
If conversation stalls, a quick round of This or That on your phones takes a few minutes: quick either/or questions, and you score when your answers match. Two of a Kind is similar: four answers, one pick each, and you score when you read each other’s mind. Then put the phones away and talk about the answers.
After the date
Send a link instead of the usual “I had a good time” message. Get to Know You is questions for two people who want to skip the small talk, answered by voice, so you get to hear each other between dates. Green Flag, Red Flag shows you one dating habit at a time and asks whether it is a green flag or a red one, which is a fun way to find out what matters to each other.
- Get to Know You2–8 players · 11 minQuestions for two people who want to skip the small talk, answered by voice.
- This or That2–8 players · 6 minQuick either/or for two or more. Score when your answers match.
- Two of a Kind2–8 players · 7 minFour answers, one pick each. Score when you read each other’s mind.
- Green Flag, Red Flag2–8 players · 8 minOne dating habit at a time. Is it a green flag or a red one?
- What’s your first-date style?1–12 players · 4 minThe planner, the charmer, the slow burner, the romantic or the funny one. Eight questions on how you really date.
- Date Night Dilemmas2–8 players · 8 minWould you rather, for couples. Pick a side, then defend it.
How to suggest a game without it feeling strange
The trick is to keep it small and give an easy out. Some lines that work:
- “I found a silly either-or game. Want to see if we match?”
- “I took a quiz on what kind of dater I am. I need to know your result.”
- “I am bad at texting. Want to answer some questions by voice instead?”
If they say no, that is fine. The point is to have fun, not to get through a game.
It also helps that there is nothing to install. They tap a link, the game opens in their browser and they can play as a guest, so you are not asking them to download an app or sign up for anything on a first date. If you are sitting together, show them the QR code instead of sending a link.
Playing between dates
Early on, it can be hard to know how much to message. A Letternerd room that runs over several days takes the pressure off: a new question is waiting, you each answer when you are free, and there is always something to talk about next time. Date Night Dilemmas is would you rather for couples, and In Sync scores you only when you both pick the same thing. Both start at two players and need no account to join.
Play the games from this post
Free in your browser. Share the room code and everyone joins from their own phone, no signup.
- Get to Know You2–8 players · 11 minQuestions for two people who want to skip the small talk, answered by voice.
- This or That2–8 players · 6 minQuick either/or for two or more. Score when your answers match.
- Two of a Kind2–8 players · 7 minFour answers, one pick each. Score when you read each other’s mind.
- Green Flag, Red Flag2–8 players · 8 minOne dating habit at a time. Is it a green flag or a red one?
- Date Night Dilemmas2–8 players · 8 minWould you rather, for couples. Pick a side, then defend it.
- In Sync2–8 players · 8 minAnswer at the same time. Score only when you both pick the same thing.
- What’s your first-date style?1–12 players · 4 minThe planner, the charmer, the slow burner, the romantic or the funny one. Eight questions on how you really date.
- Dealbreakers2–8 players · 8 minCould you live with it, or is it over? Find out where your lines are.
Frequently asked questions
What are good first date questions?
Light, open ones that invite a story, like “What made you laugh this week?” or “Which trip do you still talk about?” Skip exes, money and anything that sounds like a test.
What games can new couples play online?
On Letternerd, try This or That, Two of a Kind, Get to Know You and Green Flag, Red Flag. They are free in the browser and start at two players.
Is it weird to play a game on a first date?
Not if it is short and optional. A five-minute either-or game can break the ice. Suggest it lightly, and put the phones away afterwards.
What should you not ask on a first date?
Avoid questions about exes, money, their body or where the relationship is going. Those can wait until you know each other better.
Can we play games for new couples over text?
Yes. Send a Letternerd link in your chat and start the room over several days. Each of you answers when you are free, on your own phone, with nothing to install.