Want to try something a little different on your next date? Use a dating icebreaker to spice up your conversation and connection.
We’ve broken down the best questions for your first date, dating app conversations, and topical icebreakers to get you on the path from the first date to soulmate.
15 Best Icebreaker Questions for Your First Date
It’s natural to be a bit nervous on the first date. Having a few icebreaker questions in mind can relieve some of the jitters. Start with something light-hearted and engaging before moving on to deeper questions. Remember to ask open-ended questions to keep the conversation flowing.
A great conversation starts with a comfortable space for each person to ask and answer questions. Think of it like a ping-pong match where the ball goes back and forth, not a one-sided rapid-fire pitching machine.
Memorize a few questions below to help get you started, then ask deeper questions to follow up.
- What is the thing you were most excited about buying this year?
Besides how they spend their time, it’s interesting to hear how they spend their resources.
For example, if their answer is: “I saved up for an e-bike.” Then you can ask about what made them decide. Was it for exercise or because they’re super into sustainable living? How did they choose which one to purchase? Did they have to give up anything to save for this? Do they have any funny stories about learning to ride a bike?
- As a kid, were you a saver or a spender?
- Do you enjoy shopping and researching purchases?
- If you had to delete all but three apps, which ones would you keep?
This is a great question to learn more about what your potential match finds important or entertaining. Are TikTok, Instagram, and Spotify at the top of their list, or could they not live without their dating app, stock portfolio, and workout trackers? Their app choices will probably give you insight into where they spend their energy.
- Are you an early adopter of technology or a wait-and-see person?
- What app has made the most significant difference in your life?
- Are you tech-savvy or tech-challenges?
Believe it or not, having great conversation can be one of the best icebreakers. Knowing what to say is one element, but knowing how to continue a conversation and end it on a high note is a skill you can take with you for life. Here’s how!
Communicate With Confidence
Do you struggle with small talk? Do you often run out of things to say or feel awkward and self-conscious in social situations? Our Conversation Mastery Course teaches you the secrets of master conversationalists and gives you the skills you need to have confident, engaging, and captivating conversations with anyone, anywhere.
- What family member are you closest to?
Family dynamics affect relationships, and asking this type of question can provide insight into the person your date is and the family they grew up in. They might talk about the person who cared for them when they were sick, the grandmother who was their biggest cheerleader, or the crazy aunt who brought them zany presents from abroad.
Phrasing the question this way is also a little less intimidating than, “Tell me about your childhood.”
- Do people tell you that you look or act like a specific family member?
- Are there any family traits or habits handed down through the generations?
- Do you have any famous (or infamous) relatives?
- What would be your dream job if money didn’t matter?
You might already know about their current job, but their dream job may surprise you, giving you a perfect chance to ask for more.
- What about that job intrigues you?
- Is there a chance they’ll ever pursue it?
- If it’s something like an NFL quarterback, it gives you some breadcrumbs of other questions: Did they play football as a child? Was there an injury or experience that stopped them from continuing? Who mentored them? Were those their glory days?
- If they made a movie of your life, what genre would it be, and what kind of character would you be?
First, it tells you if they know their movies, and if your favorite weekend activity is heading to the theater, this may be really important. It also tells you about their movie preferences. Are they into rom-com or sci-fi? Which character are they in their chosen movie—the hero or the villain?
You can learn a lot about their life story with just one question. And be prepared to share which movie best reflects yours as well!
- What is your favorite movie of all time?
- What scene from a movie scared you as a child?
- What was the first movie you saw in a theater?
- Do you have a “bucket list,” and have you completed anything from it?
Many people have ideas about what they want to do or achieve in life—whether jumping out of an airplane, opening their firm, or visiting every continent. But what does your date want to do, accomplish, or see? Have they done any of it? Does their answer reveal that they’re dreamers or planners who already know the path?
- Did you actually write a bucket list?
- Is there anything that was initially on your list that you’ve changed your mind about?
- What excited you about doing that activity?
- What was the first record, tape, or CD you owned?
Asking about their musical interests is a great way to determine if you’re in tune. Having similar tastes in music can help you bond. You can discuss your favorite bands, concert venues, and most memorable concerts.
Remembering a pleasant experience and sharing that with a new friend is a great way to learn about a person and connect their experience with yours.
- Did you ever play a musical instrument or sing in a choir?
- Do you like to see the same band over and over or see a new band each time?
- What’s your craziest concert story?
- What’s one thing that never fails to make you cringe?
While you don’t want your date to turn into a venting session, if asked the right way, you can find something you have in common that could lead to future dates.
Do you share a mutual dislike for poor grammar, the Kardashians, or chronic tardiness? Or do you both hate break room coffee or texting at the dinner table?
These types of mutually cringy things tap into the Similarity Attraction Effect, which means we like people like us. And you can capitalize on this in dating. Mutual likes, or dislikes, open the door for sharing interests like bad grammar memes or discovering the most phenomenal cup of coffee.
Learning what is cringe-worthy to them (and noticing what their facial expression looks like when describing it) may give you clues about their tolerance, habits, and how they’d be as a potential partner. Don’t miss the Flirting Body Language Guide if you want to learn more about reading non-verbal cues.
- If you had an unexpected day off tomorrow, what would you do?
Everyone likes to spend their free time differently. Knowing what your date would do with an unexpected day off could tell you a lot. Do they prefer their routine, or are they spontaneous? Would they tackle a project, take an impromptu road trip, or spend the day binge-watching Netflix? Would they prefer to be with others or alone?
- If you could change your work week, how would you change it?
- Have you ever had extended time off?
- Do you prefer planning out your weekend or being spontaneous?
- If you hosted a podcast, what would it be about?
This question could elicit a wide range of answers, from something they like to talk about a lot—such as the key to the perfect butter board or their favorite sports to something they’re really well-versed in—like starting a business, writing a book, or the best place to travel on a budget.
You might also learn that they already have a podcast or have been a guest on a podcast, which allows them to share more without sounding like they are full of themselves.
- What is your favorite podcast?
- Are you comfortable speaking in public?
- When do you typically listen to podcasts?
- As a child, what did you most look forward to about growing up?
Your date may laugh and say, “Everything, and now I realize that childhood is easier than adulting!” or they may reply with something like eating pizza every night or staying out as late as they wanted. Either way, you can learn something fun.
- Who was the stricter parent (or was your mom/dad strict)?
- Were you a rule follower or a boundary pusher?
- What career did you think you’d have as an adult?
- If you could eliminate one thing from your daily routine, what would it be?
Be curious about what they would like to eliminate and why. Is it because they hate commuting because it’s time they’d prefer to be spending on something they’re passionate about? Or do they really just hate cleaning their house and feel it’s a necessary evil? By asking this question, you can start to understand what makes them tick.
- What would you do with that time if you didn’t have to do that thing?
- Do you believe in getting the worst chores done first or leaving the worst for last?
- Would you prefer to work so you can hire someone to do the things you don’t want to do or save money and do the things you don’t like, anyway?
- What is your least favorite routine chore?
- What is your favorite season of the year?
This answer to this question can go in so many directions, and you may learn something interesting about their favorite family traditions, professional influences, and hobbies.
- Do you still carry on those traditions?
- How do you celebrate the beginning of [insert season]?
- Have you ever lived in a place with distinct seasons (or without different seasons)?
- What types of vacations do you enjoy most?
Professor Richard Wiseman conducted a study and found that 18% of couples who discussed travel went on a second date, compared to only 9% of couples who talked about movies.
And instead of asking where someone has traveled recently, which can quickly lead to an awkward silence if there have been no recent trips, ask what type of vacation the person enjoys and where they dream about traveling. Travel usually brings up good feelings and can lead to great conversation and possibly second dates.
- What is your craziest travel story?
- Where is somewhere you’d like to visit in the winter?
- Have you ever been lost in a country where you didn’t speak the language?
Interested in mastering the first impression? Dig into this article with the First Impression Cue that Men and Women Find Most Attractive.
- What is something you love doing?
You may already have an idea from their dating profile or if the friend who introduced you said you share a love of musical theater, but this question allows your date to expand upon or go deeper into what you already know.
If you know very little about the person, it will tell you what their passion projects or hobbies are. Finding out what your date likes to do in their spare time or for free says a lot about their personality and character—what really matters to them. The answer will help you decide if you have similar interests.
- Have you ever thought about incorporating your passion into your profession?
- Was there someone that was instrumental in you learning that hobby?
- Do you do your hobby for fun or competition?
12 Best Dating App Icebreakers
If you’re one of the 323.9 million people who used dating apps in 2021, you’ll understand why having a good opening line to start the conversation is essential. A good icebreaker is so much more interesting than “Hey” or “How are you” Plus, it’s much more likely to elicit a response and set you apart from the other profiles.
Here are three tips to start you off on the right foot:
- Find common ground. Look for something in their profile you can comment on and relate to.
- Ask about them. People love to talk about themselves.
- Be playful. Use emojis to insert a fun personality into the message—but be careful not to go overboard.
- Where do you listen to music? I’m always up for dancing to some great tunes.
Swap dancing with cycling, climbing, wine tasting, or any other activity your potential match has mentioned they enjoy. People love others who share their passions, so asking for a recommendation is sure to elicit a response.
- I love traveling, too. When did you visit [insert country of profile photo]?
People love posting travel photos on their profiles. It offers an easy connection point for conversation.
- Your eyes make you look so kind in that second picture. Where were you when that was taken?
Everyone loves a compliment that doesn’t sound cheesy or insincere. If you’re lucky, they’ll tell you more about themselves and the occasion that prompted that picture (which hopefully wasn’t taken by their ex!)
- You’re into surfing! That’s so amazing. I love being in the water, too. If you could surf anywhere in the world, where would it be?
By mentioning something in their profile, it shows you actually took the time to read through it instead of just swiping on the bathing suit photo.
5. I’m happy you swiped right! I saw you like the Dodgers, but I’m a Giants fan. I guess that means we’re enemies, but I hope we can share our love of baseball.
Don’t be afraid to show your playful side! They’ll likely be flattered that you’re excited to talk to them. Worst case, they don’t have a sense of humor.
6. If you could describe yourself with three emojis, what would they be?
When a dating profile has little to go on, a few emojis can tell you a lot!
7. Important question: What do you think is the best way to prepare for a zombie apocalypse?
Let them see your quirky side to see if they have one, too. It shows you enjoy having fun and have a sense of humor.
8. What’s the funniest nickname someone’s ever called you?
Asking them to reveal a little of themselves is a great way to start the conversation.
9. What is your favorite sushi roll?
A question about food is always pretty harmless. Plus, you might be able to tell a lot about a person based on how they roll (pun intended).
10. What was your favorite Saturday morning cartoon growing up?
People are eager to respond to questions that make them remember a positive time, and invoking a bit of nostalgia can set the tone for more connection. Plus, you might find out you both have a love of SpongeBob.
11. Let’s play two truths and a lie. You go first!
This one is perfect for profiles that don’t give you a lot of information to play off of. You can also flip the script and start with one of your own.
For example, you could write. Let’s play two truths, and I lie. I’ll go first. I eat for a living. My parents both ran the Boston Marathon last year. I got no grades in college. What are your guesses, and share yours.
12. Ok, so I’m sure you heard this all the time, but that dog is adorable. Is it really yours, or is he just your wingman for attracting people who love dogs (insert wink emoji)?
Pet parents love talking about their animals as if they were their children, so commenting on the photo of your potential date with an animal is like complimenting their child. It’s a surefire way to get them to respond and maybe set up a puppy (and human) play date.
Looking for more inspiration to up your online dating communication? Dive into our 160 Best Tinder Conversation Starters for Instant Responses.
13 Questions About Family
Families play a significant role in an individual’s development, sense of belonging and purpose, self-esteem, and communication skills. Learning about their family dynamics and the people who raised them can give you a window into who they might be as a partner.
How were they motivated? Was their family reserved or super affectionate? Were they encouraged to explore or expected to perform? Rather than starting with these probing questions, start off slowly with one of these instead.
- Do you have siblings?
- Where are you in the birth order?
- What person in your family would you most like to travel with?
- Who is the planner in your family?
- What is your birth order?
- Who would you like to know better?
- Which television show best portrays your family situation?
- Who is most likely to appear on America’s Most Wanted?
- What’s your favorite family memory?
- Tell me about your mom.
- Is there a crazy Aunt Shirley in your clan?
- Do your parents live in the house where you grew up?
- Would you ever move back to the city where you were raised?
17 Icebreaker Questions about Food
Getting to know someone through their food preferences is generally non-threatening and a good way to connect and even set up a second meeting to bond over the best burrito. Here are a few to determine if getting takeout together is in your future:
- What was your least favorite food as a child?
- What did you eat for breakfast?
- If you had to eat one meal every day for the rest of your life, what would it be?
- What’s the weirdest food you’ve ever eaten?
- What is your favorite meal to cook?
- Sweet, salty, or sour?
- Eat out or eat in?
- If you were a vegetable, what vegetable would you be?
- Coffee or tea?
- What’s the weirdest food you have ever eaten?
- How do you like your eggs?
- Who taught you to cook?
- What’s your favorite breakfast cereal?
- What is your favorite restaurant?
- What is something you can’t cook?
- What is your favorite dessert?
- If you could eliminate one food so no one could eat it ever again, what would you destroy?
12 Icebreaker Questions for Deeper Conversation
According to psychology professor Arthur Aron, conversation helps promote connection and develop romantic love. To move toward a deeper connection, consider asking questions that uncover an additional layer.
- What’s the best piece of advice you’ve ever been given?
- When you die, what do you want to be remembered for?
- What would the title of your autobiography be?
- Who most influenced who you are today?
- What’s the most out-of-character thing you’ve ever done?
- If you could be guaranteed one thing in life (besides money), what would it be?
- What was your favorite age?
- Do you think you could live without your smartphone for 24 hours?
- What’s your love language?
- What’s one thing your parents don’t know about you?
- What would you like to do when you retire?
- What is the best perk you have ever enjoyed at a job?
12 Quirky Icebreakers
Don’t be afraid to infuse some quirkiness into your conversation. It can be a great way to discover whether your date has a sense of humor.
- What’s your grossest hidden talent?
- If you had a time machine, would you go back in time or into the future?
- You can have an unlimited supply of one thing for the rest of your life. What is it?
- What’s your best scar story?
- How long do you think you would last in the Hunger Games?
- If you could add a word to the dictionary, what would you add, and what would it mean?
- If you could add anyone to Mount Rushmore, who would it be?
- If you could rename yourself, what name would you pick?
- If you could have someone follow you around all the time, like a personal assistant, what would you have them do?
- If you could be on a reality TV show, which one would you choose and why?
- What would be the most surprising scientific discovery imaginable?
- What “old person” thing do you do?
10 Funny Icebreaker Questions
All genuine laughter feels good, and shared laughter brings people closer, strengthening relationships. So, what could be better than connecting with your date over a good chuckle?
- What is one article of clothing that someone could wear that would make you walk out on a date with them?
- What is your most used emoji?
- Have you ever been told you look like someone famous?
- What’s the most embarrassing fashion trend you used to rock?
- You have your late-night talk show. Who do you invite as your first guest?
- If you were famous, what would you be famous for?
- You have to sing karaoke. What song do you pick?
- What would you choose if you were left on a deserted island with either your worst enemy or no one? Why?
- Who is your celebrity crush?
- Were you the teacher’s pet or the troublemaker in school?
Fun and Games Icebreakers
Playing a game of 20 questions, or would you rather, is an entertaining way to learn what you have and don’t have in common with your date.
Would You Rather?
- Drink coffee or tea?
- Get up early or stay up late?
- Snack on popcorn or M&Ms?
- Travel or stay home?
- Live in the ocean or on the moon?
- Travel back in time to meet your ancestors or to the future to meet your descendants?
- Lose all of your money or all of your pictures?
- Have invisibility or flight?
- Live where it only snows or the temperature never falls below 100 degrees?
- Always be slightly late or super early?
- Be the funniest or most intelligent person in the room?
- Be an Olympic gold medalist or an astronaut?
- Eat crunchy peanut butter or smooth?
- Be rich or famous?
- Be smart or funny?
Find 246 best “Would You Rather” questions for a fun game night and adapt them to your date.
Similarly, playing Have You Ever is an engaging way to learn about some of your date’s experiences.
- Been out of the country?
- Ridden on a motorcycle?
- Lived in another state?
- Gotten a tattoo?
- Planted a garden?
- Experienced a natural disaster like a hurricane or tornado?
- Won a contest?
- Eaten a whole pizza by yourself?
- Done any extreme sports like skydiving or bungee jumping?
- Texted the wrong person something juicy?
- Slept on the job?
- Dined and ditched?
- Had a near-death experience?
- Worn your underwear two days in a row?
- Drank soda, laughed, and had it come out your nose?
- Regifted something?
- Gone tent camping?
- Built a snowman?
- Touched your tongue to a frozen lamppost?
- Had to get stitches?
- Talked your way out of a speeding ticket?
- Sung karaoke?
- Lied about your age?
- Skinny dipped?
- Played strip poker?
- Had a wardrobe malfunction?
Dating Icebreakers 101
Dating can be hard, but it doesn’t have to be. By leveling up your conversation game, you can find out if your potential connection is a home run or a dud. Remember these four things:
- Be interested. Ask questions about the person conversationally and give them time to answer. Most people are content to talk about themselves.
- Return the volley. Once you’ve asked a question and they’ve responded, hopefully, they’ll ask a question in return. Instead of saying “yes” or “no,” expand upon your answer and then toss them a question back using phrases like “Has that ever happened to you?” or “What’s your favorite [insert topic]?”
- Find common ground. Look for areas of mutual interest and capitalize on them. Most people like someone who likes the same things as they do.
- Don’t be too serious. Try to be natural with your questions so they don’t come across like an interrogation. Remember, dating should be fun! Witty banter helps you discover if their sense of humor vibes with yours.
Want some more icebreakers? Try these: 21 Best (Non-Boring!) Large Group Icebreakers For Work