50 Excellent Icebreaker Questions for Dating

Dating 101
16 Oct 2023
9 min read
50 of The Best Ice Breaker Questions For Dating!

It doesn’t matter if it’s your first date or fifth – awkward silences are date killers. You try bringing up the weather or local sports teams, but that rarely leads to an interesting conversation. What can you do to keep things interesting? Try one of these 50 ice breaker questions for dating to fix all those conversational problems and rock your next date!

Why Icebreaker Questions?

“My idea of good company is the company of clever, well-informed people who have a great deal of conversation; that is what I call good company.”

Jane Austen

Icebreaker questions keep the conversation flowing and let you get to know a new friend or lover faster. With these phrases, you always act right and don’t waste time trying to guess what to say next to get the desired reaction.

Would you like to leave a good first impression? Be a good conversationalist, then! Start with insightful, serious, and funny icebreaker questions. And we will be here to help you with that. With any of the icebreakers in this list, you can spark a great conversation on your next date.

24 of the Best Icebreakers

Let’s get started with the first 24 of the best conversation starters. It’s just a few questions, but the replies you’ll get with them are multiple and truly encouraging!

1. What Was Your Best First Date Ever?

This is more than just a good conversation starter. It’s a great way to get to know another person’s dating preferences. Then, you can wow them with an amazing second date.

Related reading: Out with the Cliché Second Date Ideas

2. Can You Describe Your Dream Job?

People aren’t always in the mood to discuss their jobs, but many are happy to discuss the work they would love to do. You may even get some idea of their future goals as they answer this question.

3. If You Had Your Own Talk Show – Who Would Be Your First Guest?

Would they interview a movie star or a historical figure? This is a fun inquiry but also gives you insight into their life views.

4. What Is Your Strangest Family Tradition?

Do they join their parents for an annual family dodgeball tournament? Maybe they have a wildly competitive Christmas cookie bakeoff every winter. Just be ready to share your weird and wacky traditions in your own house.

Helpful hint: Don’t underestimate the power of a simple ‘Hey, how are you?’. People use this phrase for ages to start a great conversation – and it really works for ages!

5. What’s Your Favorite Season?

Can a winter person have a long-lasting relationship with a summer lover? There’s always hope! But you’ll know for sure if only you ask and try to build something together.

6. Tell Me 3 Memorable Moments From Your Childhood

This is one of those questions that can be fun or serious. That really depends on the life they’ve led before meeting you. In any case, you will both have something to discuss.

7. Who Was Your Childhood Actor Crush?

This is a fun topic that will let you know a bit more about the person than you realize. Did they crush on the major star or the lesser-known indie movie darling? If so, this question can lead to a highly interesting conversation!

8. If Police Suddenly Broke Into Your House, What Would You Rush to Hide?

No, this isn’t intended to determine whether you are dating a prospective felon. Most folks will answer with the one thing they are secretly embarrassed to own in their home. And it is so much fun if you know how to keep the convo going!

Related reading: 42 Questions to Ask Your Boyfriend: Grow Your Relationship Gradually

9. What Was Your Peak Embarrassing Moment in High School?

Let’s be honest. All of us have at least one memorably embarrassing moment from high school. Hopefully, enough time has passed to make this a fun question. Alternatively, you may spend the rest of the night reassuring them it wasn’t so bad.

10. Have You Ever Had a Celebrity Encounter?

People love to dish about celebrities they’ve encountered. This is a great convo starter. Also, you could learn something intriguing. Maybe that allegedly clean-cut singer is really heavily tattooed!

11. What’s Your Love Language?

If you’d like to try some deep questions, one thing to discuss is love languages. These describe how somebody shows and receives love in a relationship. If your goal is finding someone for the rest of your life, it’s something worth bringing up.

Related reading: The Love Language of Gift Giving

12. What Are Your Top Three Bucket List Items?

“Many people die with their music still in them. Why is this so? Too often it is because they are always getting ready to live. Before they know it, time runs out.”

Oliver Wendell Holmes, American jurist and poet

You never know how long the rest of your life is going to be. Spend some time going over the dream vacations, achievements, and other goals both of you yearn to accomplish before you kick the bucket.

13. What’s Your Favorite Movie That Nobody Else Knows About?

There’s something special about finding a movie nobody else knows about. When that happens, people love to share. This makes this one of the best date questions for getting somebody to open up about things that excite them.

14. What 3 Things Would You Bring to a Deserted Island?

Are they a practical survivalist who would choose a life straw, matches, and a handy pocket knife? Would they choose their pet cat, books, and favorite wine? Compare and contrast your answers to see how your choices align.

Food-related questions are great conversation starters

15. What’s Your Favorite Food to Order Out? Cook at Home?

There are a few variations of this question. You could ask them what dish their friends always ask them to bring to parties. If the response is soda and napkins, you should plan to do most of the cooking in the future.

16. Name One Food You Will Never Eat Again

Most of us have at least one thing our parents served that absolutely grossed us out. Fortunately, when we become adults, we never have to touch that food again.

17. Who Sells The Best Piece of Pizza in Your City?

The subject of pizza can be contentious, but it’s the kind of debate fodder that’s more fun than serious. Just one question. Will your relationship survive the great pineapple-on-pizza argument?

18. What’s The Best Place in Your Area for a Romantic Date?

You’re ready to take your relationship to the next level. This means it’s time to pull out all the stops and really impress them! Shouldn’t you learn more about what they look for in a romantic date?

Related reading: The Great Outdoors – 27 Date Ideas in the Open Air

19. What’s The Most Spontaneous Thing You’ve Ever Done?

“Adventure is allowing the unexpected to happen to you. Exploration is experiencing what you have not experienced before. How can there be any adventure, any exploration, if you let somebody else – above all, a travel bureau – arrange everything before-hand?”

Richard Aldington, English poet

This is a great compatibility question. If their idea of spontaneous involves world travel with less than a week’s notice, and yours is buying a cheesecake, you may have some things to work out!

20. What Is the Most Important Product Invented in the Past 100 Years?

Would you like to discuss how the two of you view technology or navigate a world of quickly emerging scientific progress? If so, this is a great talking point to get that convo started.

21. Bungee Jumping or Skydiving?

Maybe the best reply is neither! It’s an enjoyable question regardless. Besides, you should want to know whether your potential mate spends their time chilling with friends or pursuing the ultimate adrenaline rush!

22. What Would You Want to Have in a Zombie Apocalypse?

Some of us would huddle away in a bunker with a supply of snacks and water. Others would form an army of friends to ensure the zombies didn’t take over. Sure, it’s a silly question, but most folks enjoy discussing these things for fun.

Related reading: 21 Questions for a New Relationship

23. You Are Home Sick as a Kid – Are You Watching Cartoons or a Game Show?

You’re too sick to go to school on Monday morning. Did you lay on the couch and binge-watch game shows or was it all-day cartoon network? Hopefully, they didn’t have ‘rents who believed that being too sick for school also meant being too sick for TV.

24. What’s Your Favorite Thing to Do on a Lazy Sunday?

They believe Sundays are for napping and drinking beer. You think it’s the best time to take care of all of those extra household chores. Can you make things work out? Let the debate begin!

A few questions more to break the ice

Ready For More? Check Out 25 – 50 Ice Breaker Questions for Dating!

Still hungry for more icebreaker questions? Here are 25 more questions for your inspiration:

  1. Do you think most people can be trusted?
  2. What’s the worst advice your parents ever gave you?
  3. Are you still friends with your group from high school?
  4. What has a potential partner done to turn you off immediately?
  5. What are the best and worst things about your current job?
  6. What’s the most fun you’ve ever had as an adult?
  7. What was the first record you ever bought or downloaded?
  8. Do you have any tattoos? Which one is your favorite?
  9. What part of your daily routine do you refuse to skip?
  10. What is your favorite smell?
  11. If you left (insert country) – where would you live?
  12. What was your favorite elementary school game?
  13. Who is your favorite cartoon character?
  14. How long have you known your best friend?
  15. Finish the sentence – I would love an unlimited supply of…
  16. What 3 things do you always grab when you grocery shop?
  17. What’s your favorite song for car trips?
  18. Who is your biggest celebrity crush? Your weirdest?
  19. What’s your comfort food?
  20. Are you a Halloween or Christmas person?
  21. What’s The Best Book You’ve Read This Year?
  22. Do you prefer city or country living?
  23. What made you choose an online dating app?
  24. What’s your favorite item in your home?
  25. Do you watch or play sports?
  26. What is your favorite board game?

What to Avoid

There are some volatile topics you should probably avoid. Most people don’t want to discuss their past romantic relationships. If you ask, it will seem more like an interrogation than an attempt to get to know them better. That’s the last thing you want.

You will also want to avoid anything you don’t want to answer yourself. If you ask a question, it’s fair game that your date asks follow-up questions.

Finally, while it’s okay to ask deep, thoughtful questions you don’t want the talk on a date to turn dark. It’s a date, not a debate or therapy session.

Ice breaker questions for dating: FAQ

Icebreaker Questions for Dating – Frequently Asked Questions

Do you have questions about icebreaker questions? Here are some frequently asked questions. You may find the answer you need here.

1. What Makes a Good Icebreaker Question?

Good icebreaker questions are conversation starters. You know you are on the right track if your date is enthusiastic about answering, and asks you their own questions.

2. Should I Ask Serious or Funny Icebreaker Questions?

That depends on the mood. Don’t ruin a light moment with a bunch of deep questions. Don’t ruin a serious moment with silly or “fluff” questions. Read the room to avoid even more awkward silence.

3. When Do I Ask an Icebreaker Question?

Ask an icebreaker when the date conversation hits a lull. You can also use these when you are messaging on dating apps and just getting to know a new person.

4. Is It Okay to Ask Deep Questions?

If you want a deep conversation, ask deep questions. There’s nothing wrong with posing deeper questions on topics that are important to you. In fact, this is a way to get those dealbreaker topics out on the table. The important thing is to respect the other person’s boundaries. They may not be willing to delve into certain topics so early in your relationship.

5. What to Do When a Question Falls Flat?

You want to ask only the best questions, but sometimes things fall flat. For example, you ask your date about their funniest talent, but they give you a blank stare. You’ve put them on the spot, and now things are awkward. What do you do?

The best strategy is to move on. You don’t need to spend several minutes apologizing or explaining. Although, you might want to take a break from questions. Instead, suggest some alternative activities to spend some time putting some distance between yourselves and that awkward moment.

Final: Advice For Asking Icebreaker Questions For Dating

Remember that the point of these questions is to keep your date interested in talking with you. Use some of the questions listed above, or spend a bit of time to think of some ideas of your own. Whether you want a serious dating relationship or just a good friend, it all starts with the ability to talk to one another.

Dating Tips Author
Shelly Standford
After a devastating relationship breakup, I threw myself into the dating scene by registering on Hily. I had over 100 dates - some absolute disasters, some pretty average, and some that were actually great. So many stories to tell and insights to share with you guys!

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