First Date Questions And Conversation Starters

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dating conversations
Before discussing some good questions to ask on a first date, I wanted to offer several tips on first date conversations in general.

First, you should ask your questions with a purpose. Specifically, you should be trying to determine if this is someone you would like to continue to spend time with. Don’t just find a bunch of questions on the internet to ask just so you can “fill the silence”. While I will provide examples it’s best if you ask yourself this question: What’s important to me in a relationship? Whatever you decide is important should be the starting point for the questions you want to ask.

Second, you’re not going to want to ask questions that can simply be answered with a “yes” or a “no” if you’re concerned with keeping the conversation going. As you’ll see below, none of the questions can be answers simply. Most will require thought or at least some explanation when answered.

Finally, don’t get so obsessed with asking a list of specific questions that you end up putting you’re dating on an “interview”. Allow the conversation to have a life of its own. If it never finds a life of its own then at the very least mix things up so there are some serious questions and some light-hearted ones. Also, don’t assume you’re the only one who should ask questions…allow your date to ask questions as well!

Remember! These questions are just examples. If you are serious about finding a relationship you need to decide what’s important to you and base your questions, at least in part, on these areas.

First Date Conversation Topics: Learning About Your Date

  1. Do you believe in living happily ever after?
  2. Do you believe in love at first site?
  3. How close are you to your family?
  4. How old were when you had your first girlfriend/boyfriend?
  5. How do you feel about your job?
  6. Do you enjoy spending time alone?
  7. What accomplishment are you most proud of?
  8. If you had a big problem, who would you go to for advice?
  9. Would you consider yourself more logical or artistic?
  10. If you were given a million dollars but couldn’t spend any on yourself, how would you use it?
  11. What are some things in life that annoy you?
  12. Have you ever read a book that changed your life?
  13. Do you like children? Would you like to have them?
  14. What do you think is the biggest problem in the world today?
  15. Do you think life is more about fate or chance?
  16. What is your biggest regret from when you were growing up?
  17. What is your strongest quality that you bring to relationships?
  18. What in life makes you the angriest?
  19. If you could ask God one question, what would it be?
  20. What makes you feel the most loved?
  21. Have you ever stolen anything?
  22. Do you rely more on facts or feelings when making decisions?
  23. What goals would you like to accomplish in the next five years?
  24. Do your parents still have a strong relationship?
  25. What are you most passionate about in life?

First Date Conversation Topics: Just For Fun

  1. Have you enjoyed your online dating experiences?
  2. If you could travel anywhere on vacation where would you go?
  3. If you had a time machine but could only travel to the future or the past, which would you pick? Would you still go if you could never come back?
  4. What’s the worst date you’ve ever been on?
  5. What would you do if you won the lottery?
  6. Do you believe in aliens? Ghosts?
  7. Do you enjoy exercising?
  8. Do you think cheesy pick-up lines ever work?
  9. What was your best birthday growing up?
  10. If you could have one super power what would it be?
  11. What are you most scared of?
  12. If you could live in another country, which one would it be?
  13. Do you stay in touch with your friends from Grade School or High School?
  14. What is your earliest memory?
  15. Do you have any pets?
  16. Have you ever changed the oil in your car?
  17. Do you sing in the shower?
  18. If you were a fruit, what fruit would you be?
  19. If you had to pick a nickname for yourself, what would it be?
  20. Would you ever appear on a reality T.V. show if you were given the chance?
  21. What do you think technology will be like 5 years from now?
  22. Do you have any personal conspiracy theories?
  23. Where were you born? Where did you grow up?
  24. Did you have any hobbies growing up? Any hobbies today?
  25. Do you think it’s silly to look up questions to ask on your date on the internet?

If you are looking for more advice on first date topics aside from questions you could ask, my online dating guide has plenty more information on first date conversations.



About the Author:

Brad initially struggled with online dating but over time became quite successful using it. He met his wife using online dating and has been giving advice and helping people improve their results since 2007. He has written a Free Online Dating Guide to help others find success with online dating. You can learn more about his personal experience using online dating and running this website here.


  1. Asaf  September 29, 2012

    I totally disagree cuz when going on a date it’s not like going to an interview
    It should be random and funny then just going to a date ask questions feel bored and go home get creativ people

  2. Genny  November 6, 2012

    Asaf, I don’t think the author meant that you should go in with a clipboard and ask these questions as written. What you ask about will be different on every date, and how you get to the subject will be different too. For example, if I date a guy who obviously has a sense of humour I’d smile playfully and say “So, how’s this dating thing working out for you?” Chances are he’d be slightly funny and we’d share a laugh. Then if I want to know more it’s easy to carry on the topic. If I want to ask someone about their childhood or parents or whatever I say “So tell me about your family.” Maybe I won’t hear about their childhood home, their first pet or their parents, and that’s OK. After all, what they choose to tell you says as much about them as what they don’t. Whatever they say, it’s a way of finding out about them and still letting them be who they are. That’s respectful, and you can both feel good about it.

  3. sasha  July 23, 2013

    Some of the other articles were good. A lot of these questions are absolutely terrible. Don’t ask them about their previous dating. Don’t ask them what annoys them. That turns the convo negative. Women are very emotional. You don’t want them feeling negative or annoyed while forming their first impression about you. A lot of these questions are really, really bad.

    • Brad  July 25, 2013

      Thanks for the feedback Sasha. I found some of the questions you disliked to be some that worked best for me. Obviously not every question is great for every situation but I’m not sure that “women are emotional” is a great reason to avoid a topic, particularly if you feel it’s something she’d be interested in discussing.

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