Great First Date Questions (for Men)

Here are our top 15 first date questions for men to ask women.


Most couples on first dates are dead giveaways. They’re usually nicely groomed, wearing stylish clothes, and there’s a stiff formality to the way they are sitting. They scan the room, touch the table, read the menu a hundred times and only occasionally make eye contact.

This is my DiscoverHow Love Guide on first date questions for men. Some of the things in this guide can be applied by women, but if you’re looking for something more specific, check out my guide on what to talk about on a first date for women.

For many of these couples, forced small talk and embarrassing silence follow each course. They stir their dinner around their plates and their eyes wander around the room. They’re both painfully self-conscious and their conversation is probably either about the food in front of them or the weather.

Let’s face it – first dates are stomach-clenching, anxiety-filled scenarios. They can lead to awesome relationships, passionate romance or nothing at all. You’re on a date with a woman because you’re genuinely interested in getting to know her (I hope!). All you need to do is ask the right questions and she’ll not only see that you’re interested in her; she’ll also do most of the talking, allowing you to relax and be yourself.

Questions to Ask on a First Date

Here’s a list of great questions to ask on a first date:

  1. What do you hate most about the dating process?
  2. What did you want to be when you were growing up?
  3. Do you have a favourite subject at school, college or university?
  4. Do you have a nickname? What is the story behind that name?
  5. What were you like as a kid?
  6. What should I know about you?
  7. What is your biggest goal in life today?
  8. How do you enjoy spending your Saturdays?
  9. Tell me about your pet peeves.
  10. What were you like as a child?
  11. What’s your favourite movie of all time?
  12. If you could live anywhere in the world, where would it be?
  13. What makes you laugh?
  14. Who has been the biggest influence in your life?
  15. What is your favorite book?

Keep Your First Date Questions Open-Ended

Most of these questions are open ended and don’t ask for a simple yes or no answer. Make sure you follow up on her response with an answer of your own. It helps to compile a list of first date questions of your own to ask her. If you already know something about her through her friends, online dating profile, Tinder profile or otherwise, compile a list of questions that uniquely relate to her. Don’t let those awkward silences turn into date-breakers. All it takes is one good first date question to get the conversation off the ground.

Leave the Past in the Past

Don’t use the date as a time to vent about your last relationship – that is the last thing a girl needs to hear. Don’t ask her about her past relationships, and let the conversation take place as if neither one of you had dated previously. Getting to know someone is a long, slow, but very rewarding process.

Be a Good Listener

Great communication starts with being interested, questioning and paying attention to what she is saying. Let her speak and don’t be too quick to cut her off. Whatever you do, avoid being demeaning or overly questioning, and leave the controversial questions for later on. First dates are ‘getting to know you’ exercises. Ask the right questions and you might just get the chance to learn more about her on the second date.



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