79 Dating Game Questions to Keep Conversation Flowing

Use a tactic from the 60s TV show The Dating Game and have some questions ready to go so you can keep conversation flowing on your dates.

Updated May 2, 2024
Young man and woman looking at each other

Back in the 1960s, the TV show The Dating Game was racy stuff. Three unseen contestants competed for the heart of a bachelor or bachelorette, who asked suggestive questions that were met with equally suggestive responses. It was sort of like Hinge but for people with hippie hair and groovy duds. 

Sound like fun? If you'd like to host your own dating game (or get to know your Hinge date better), we have great dating game questions to get the ball rolling. 

Dating Game Questions That Spark Conversation

While you could turn this into a fun party game if you're hanging out with a bunch of other singles, you could also use a list of dating questions like this to get to know someone you're already interested in but don't know that well. Quiz your date when you first get together for coffee or dinner and let the conversation flow from there.

Quick Tip

If you're using these dating game questions on your first date, might we suggest that you don't rapid-fire the questions and make it feel like an interrogation? Instead, sprinkle the questions throughout (or use them during awkward moments) to inspire a delightful and insightful conversation. 

Unique First Date Questions

First date? No need to make it awkward. These are some great questions to keep the conversational ball rolling. 

  • Where are you from?
  • If you could work in any profession, what would it be?
  • If you could go anywhere in the world where would you go?
  • What are you looking for in a partner?
  • Are you a morning person or a night owl?
  • How do you have fun?
  • What is the last book you read, and did you enjoy it?
  • Did you go to college?
  • Who is your favorite person? Why?
  • What matters to you? Tell me about it.
  • What do you like to do when you get a week off?
  • If you attended college, where did you attend and what did you major in?
  • What are your best qualities?
  • What languages do you speak?

Romantic and Flirty Questions

It's okay to be a little flirty with your questions. After all, on The Dating Game, the questions were all flirty, and so were the answers.

Personal Questions: Background Information

It's always helpful to learn a little more about your date's background. We like these questions because they're not intrusive but can help you understand your date better. 

  • Do you have any children?
  • Describe a time when you took care of a loved one.
  • What have you always wanted to do but haven't yet?
  • What is your greatest achievement?
  • What is the longest relationship you have been in?
  • How did your family celebrate holidays?
  • If you could change a mistake from your past, what would it be?

Personal Questions: General Knowledge

If you want to dig a little deeper, you can ask some personal questions.

  • How do you comfort someone in a traumatic situation?
  • Do you see a glass-half-empty or half-full?
  • Do you give money to people who are unhoused?
  • You've just been told you have a few months to live. What do you do?
  • What do you value in a relationship?
  • What's your favorite possession?
  • Do you spend time on the internet? Which site is your favorite?
  • Who do you live with?
  • What makes you laugh?
  • Are you easily offended?
  • Where's your favorite place to spend time?
  • What's your favorite season? Why?

Related: Would You Rather: The Ultimate List of Questions

Silly Questions: Situational

Situational questions can give you insight into how your date responds to things that come up.

  • A kid comes up to you and kicks you in the shin, what do you do?
  • If you could be any animal, what would you be and why?
  • If you had a million dollars, what would you do with it?
  • You're stranded on an island. What three things do you wish you had?
  • If you could have three wishes, what would they be?
  • You need to cancel your weekend plans because of the rain. What do you do instead?
  • You are driving and get lost. What do you do and how do you handle it?
  • If you were to take a class, what would that class be?
  • If you could invite anyone to dinner, who would it be and what would you talk about?
  • Your work lets you out early, what do you do with this free time?
  • If you could be a circus performer which act would you be?
  • Your house is on fire. What do you grab as you run out?
Silly questions

Silly Questions: Just For Fun

Keep it light and fun with these silly questions. 

  • Dogs or cats?
  • What color best describes your personality and why?
  • What three things do you never leave the house without?
  • What's one word that describes your life?
  • What's your theme song?
  • What are some nicknames you've had?
  • What do you hate about dating?
  • What was the weirdest question a date has asked you and how did you respond?
  • Do you have a lucky number?

Character Questions

If it's going well, asking questions about their character could help you decide whether date two is on the horizon.

  • A mutual friend flirts with you; would you tell me?
  • A cashier gives you too much money back. What do you do?
  • A car is broken down on the side of the road; do you stop to help?
  • What do you wish others knew about your heart or the way you think?
  • What would you change about yourself?
  • What's your religion, and is it an important part of your life?

Questions About the Future

Some light questions about the future can be enlightening.

  • What do you see yourself doing when you retire?
  • Where do you see yourself 10 years from now?
  • Do you want children in your future?

Blind Date Questions

So you're on a blind date. Those can be a little awkward. But having some pre-loaded questions can help make it less so. 

  • Do you believe in karma?
  • Do you tend to make decisions based on logic or emotions?
  • Which people in your life do you value the most?
  • What does your perfect weekend look like?
  • If you could trade places with anyone for a day, who would it be and why?
  • How do you de-stress from a bad day?
  • What's the most amazing meal you've ever had?
  • What's the most fulfilling project you've worked on?
  • What's your favorite body of water?
  • What's your typical bedtime routine?

Creative Conversation Starters

The Dating Game can provide hours of entertainment for you and your friends, as well as provide creative new questions for you to use on dates. Keeping the conversation going can be difficult if you are shy or dating someone who's self-conscious, so pulling out a few favorites can help you get through any uncomfortable moments. 

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79 Dating Game Questions to Keep Conversation Flowing