We’ve all been there: You’re hanging out with someone new and attractive, but you forget what to talk about. First-date conversation starters are the secret to avoiding awkward silences and nervous laughter. 

Expressing genuine interest in your date and bringing up intriguing topics can make for an unforgettable memory (or, at the very least, a date that isn’t boring).

As you explore these questions, don’t forget to share details about your life. Research shows that self-disclosure makes you more likable and helps others feel comfortable opening up to you.

Here are the most exciting conversation starters to set yourself apart from the rest: 

Conversation Starters to Get to Know Someone

You just met someone and want to find out if there’s a spark between you. Warming up on a first date takes some time and patience. You may not want to dig into super deep or personal topics when you’re first getting to know someone. Instead, keep it lighthearted and intriguing with these unique questions:  

#1 What’s something I would never guess about you?

Most people aren’t as they appear. This question is an excellent icebreaker that helps dive through stereotypes and pre-conceptions so your date can tell you something unexpected about themselves. 

#2 If you could get on a plane right now to anywhere in the world, where would you go?

Find out if your date is spontaneous. Their dream destination might inspire some discussions about culture, food, and travel. 

#3 How do you see yourself?

Get an idea of someone’s self-perception. This twist on the classic “how do you describe yourself?” may make your date stop and think for a minute. Are they self-aware? Are they confident? How do they want the world to see them? Be prepared to answer with your viewpoint on yourself as well.    

“What we perceive about ourselves is greatly a reflection of how we end up living our lives.” -Stephen Richard 

#4 What are you passionate about?

This is vague enough to incite conversations about hobbies, creative endeavors, or philanthropic dreams. Discussions about passion can go in any direction, but they’ll always tell you more about someone’s priorities in life. Is their zest for life compatible with yours? 

#5 What is your dream job?

Instead of going the mundane route with “what do you do for a living?”, dig into your date’s ideal career. Not everyone is right where they want to be at this moment, but they may have their sights on something big and exciting. Are they motivated by potentially impacting lives, making more money, or the pure enjoyment of doing something they love? 

#6 What is your favorite ______?

Asking about someone’s favorite things is a no-brainer. Their favorite animal, favorite color, favorite book, favorite place, or favorite dessert are all simple topics to help you warm up to each other. 

#7 How do you spend your free time?

This one’s simple and easygoing. The ways someone spends their spare time reflect on their priorities and interests. You can talk about your favorite TV shows, walking trails, or leisurely activities. 

#8 If you suddenly had a billion dollars, what would you do? How would you spend your days?

Someone’s more profound mission or calling in life comes out once the day-to-day grind is off the table. Sure, most of us would opt for a month-long vacation, but then what? 

Would they start a business, a charity, or an off-grid homestead? Would they invest or donate some of the money? Would they buy a Bugatti or a designer bag? Would they finally pursue that secret dream they’ve always pushed aside because of their work priorities? Money undeniably reveals a lot about a person. 

#9 Do you have any pets?

Who doesn’t love to talk about their “fur babies”? Whether you’re a dog or cat person (or snakes or fish), dig into the topics of their pets’ name(s), breed, tricks, and personality.  

#10 When was the last time you laughed so hard that your stomach hurt?

Sociologists have found that laughter brings people together in a profound way. Discover what makes someone laugh like crazy. Maybe they’ll share a funny story with you.

#11 What’s your favorite thing about where you live?

It’s easy to get wrapped up in the drawbacks of a specific town or city: the traffic, the weather, or the high rent prices. Instead, you can learn a bit more about your date’s opinion on the positives of their current home. You may get some local tips if you’re new to the area. 

#12 When was the best year of your life so far?

This question tends to make people pause and reflect. Major professional success, positive family change, or personal growth could mark the best year of someone’s life. If your date seems interested in sharing, dig a little deeper by asking about what made that year so transformative or memorable for them. 

#13 Who do you talk to the most regularly?

The adage “you are who you hang out with” rings true for most people. Find out about your date’s closest relationships without being too nosey. 

#14 What was your favorite activity as a kid that you miss doing now?

While you may not want to dive into childhood topics immediately, this question is easygoing enough to open up a conversation about pleasant memories. After all, everyone has an inner child that used to enjoy carefree activities they may not have time for as adults. 

#15 Have you ever gone on a cross-country road trip? Would you?

The way someone travels says a lot about them. Are they into camping and road-tripping, or are they more of a flight and luxury resort-type? Ask about their favorite destinations, snacks, and playlists if they’ve gone on a road trip. If they haven’t, find out if they’ve ever considered it. If so, where would they drive?  

#16 If you just showed up in a new city, what attraction do you visit first?

These answers can go all over the place. While you might instantly hit up the best local foodie restaurant, someone else may run for the nearest historical landmark. Once again, your date’s travel preferences reveal more about their overall vibe and interests. 

#17 What is one thing you want to accomplish before you die?

OK, that’s a big one. You can open this conversation with an overview of your mission (if you have one). If your date isn’t quite sure about any lofty goals, change the topic to smaller goals for the year. 

#18 What is your favorite thing to cook?

Who doesn’t like food? Find out if your date is secretly a 5-star chef or if they prefer to go out to eat. Take a mental note of their favorite cuisine or dish.  

#19 What is your current favorite hobby or pastime? 

Adding the words “current favorite” makes this topic a little more casual. People are prone to change and may only be experimenting with a sport, craft, or social hobby

#20 If you had no obligations, what would your perfect day look like?

Find out what they prioritize and enjoy when all other obligations are (hypothetically) out of the picture.

#21 What makes you feel relaxed?

Stress is practically ubiquitous in the modern day. See how your date likes to unwind and notice if their stress level or pace of life is compatible with yours.

#22 What’s your favorite and most minor favorite thing about your job? 

Instead of focusing on only the positive or negative, get their opinion about both sides of the coin. Maybe you can laugh about a shared pet peeve. Perhaps you’ll notice some green (or red!) flags about their attitudes related to work. 

#23 When you’re having a bad day, what thought or image instantly brings a smile to your face?

Puppy kisses, soothing beach waves, or goofy memories? See what makes your date smile or laugh on difficult days. 

#24 How do you spend an average weekend? 

The key word here is “average.” While many emphasize their favorite vacations and events, this question lets you peek into your date’s weekly routines to see if they might be compatible with yours. Do they go out with friends every Friday night, or do they have a weekly Netflix tradition to unwind?

#25 If you could host a dinner party with any historical or influential person, who would it be? 

Artist, musician, actor, author, politician, revolutionary, philosopher, or comedian? Regardless of who they’d invite, there’s a story behind their choice. What questions would they ask them? What would they want to learn from them? 

#26 Have you ever thought of starting a side hustle, or are you working on one currently?

The modern economy has led many people to pursue side hustles for financial reasons or to make time for their true passion outside their careers. This question lets you gauge your date’s ambition.

#27 What musician, concert, or album has impacted your life?

Music helps people through hard times and enlivens their celebrations. Often, certain songs or bands genuinely change somebody’s life. Shared musical interests can be a great sign of compatibility. You may also discover a new artist or genre you want to listen to. 

#28 What’s your idea of a great morning?

Find out if they’re an early bird or a night owl. Maybe a coffee date is in your future. 

#29 If you could be known for one thing, what would you want to go down in history for?

The idea of legacy can be daunting. But when it’s all said and done, most people are only remembered for a handful of things. Perhaps it’s their sense of humor, creativity, deep love for their family, or generosity. Get some insights into your date’s character and ambitions. Don’t forget to share what you want to be remembered for. 

#30 If your friends or family members could describe you in one word, what would it be?

This could elicit a humorous answer or reveal something more profound. If you already asked how your date would describe themselves, it may be interesting to see how the answers line up.  

#31 Do you consider yourself an introvert or extrovert? 

Plain and simple. Most people fall somewhere in between, depending on the situation. 

#32 What is something you regularly buy that’s expensive but worth it?

How people spend their hard-earned money is a definite clue into their highest priorities. But this question adds a flair of fun because it shows if or how your date is willing to splurge for something that truly brings them joy. 

On the other hand, it could reveal hints of superficiality or frivolous fun. But don’t judge them too hard; you probably have a silly expense to share!  

#33 If you were to write a book, what would it be about? 

Surveys show that over 80% of Americans want to write a book someday. If your date falls under this category, what would they write about? Whether the genre is a juicy romance novel, a southern cookbook, or a memoir of their life, you’ll learn a bit more about your date’s imagination. 

#34 What are your quirks that most people don’t know about?  

Everybody has a little bit of weirdness in them, right? See if your date will share some of their funny or unusual habits. You never know. You may have similar eccentricities. 

Funny Conversation Starters for Dating

Humor is one of the most sought-after traits in romantic partners. If you can make someone laugh with intriguing questions or witty banter, you may have some luck for a second date. At the very least, you can show your less-serious side. 

#35 If you had a theme song for your life right now, what would it be? 

The soundtrack playing in someone’s head says much about this chapter of their life. Ideally, this opens up a lighthearted conversation about theme songs and music.  

#36 What’s the most ridiculous pick-up line you’ve ever heard?

Whether trying to talk to a girl or approach a guy, pick-up lines are notoriously absurd and silly. Thankfully, this conversation gears at making fun of those corny one-liners rather than using one. 

#37 What is an odd or random talent you have?

Some talents are hilariously useless or just outright strange. Share a laugh over your quirky talents: accent impersonations, handstand skills, or the ability to solve a Rubik’s cube in 10 seconds? Everybody has some hidden talent, right? 

#38 If you could read peoples’ minds, would you?

It’s a tricky question… there are some weird minds out there. 

#39 If you could have any superpower, what would it be? 

Speaking of superpowers, your date’s answer to this one reveals more of their personality’s playful side. Would you choose invisibility, teleportation, ultrasonic hearing, or the ability to fly? 

#40 If you could swap places with anyone for a day, who would you choose?

Would it be someone they know personally or a celebrity? Perhaps Oprah? Lebron James? Mariah Carey? Will Smith? Find out whose shoes they would want to walk in for 24 hours. 

#41 What would you do if you won the lottery?

You’d be hard-pressed to find somebody who hasn’t thought about it. This one is lighthearted but discloses some of your date’s inner desires.

#42 What’s a cheesy song that you love singing along to?

There’s no shame in singing along to the latest Justin Bieber hit or jamming to The Temptations when you’re “in your feels.” Whether it’s a throwback tune or a modern hit, everyone has a secret corny song they’d probably sing karaoke to after a few drinks. 

#43 Have you ever been given a funny nickname?

Family and friends have a knack for giving nicknames. Find out about your date’s childhood moniker or funny pet name in high school. Why were they given it? Did they hate it or find it to be hilarious?  

#44 If you were stranded on an island with only 3 things, what would you have with you?

Ah, the classic “stranded on a desert island” question. It’s timeless and, frankly, still relevant in adulthood. Does this one show where their priorities are: survival or comfort? 

#45 What’s the most spontaneous thing you’ve ever done?

Have they ever left for an impromptu road trip, impulsively booked a flight, invested in a new hobby, or decided to go sky diving? The willingness to jump up and do something wild is super exciting for the adventurous type. On the other hand, it may demonstrate their irresponsibility. Either way, you’ll find out if your date is more of a planner or a “go with the wind” person. 

Would You Rather First Date Questions

“Would You Rather” isn’t just a game for kids. It can open up realms of exciting conversations that uncover more about your date’s opinions and outlook on life. These icebreakers are less pressure than an open-ended question because they allow for playful banter about which selection is better than the other. 

#46 Would you instead find your soulmate or a suitcase with a million dollars?

This is a pretty loaded question, but it’s a two-in-one opportunity. Find out if they believe in “soulmates” and see if they approach the suitcase full of cash with a logical or a joking mindset.

#47 Would you rather be able to see 20 minutes in the future or 20 years in the future? 

There’s a big difference between the two. A “crystal ball” would undoubtedly come with some risks. If you always knew what would happen next, would life be fun? 

#48 Would you rather be super physically attractive but dumb, or very intelligent and not very attractive? 

If it seems like an easy answer, you may be surprised by their response. You can always get smarter, but can you always get more attractive? The opposite could also be true. This question can dive into deeper topics about the possibility for self-improvement, the idea of innate intelligence versus capacity to learn, and even opinions on fitness or beauty. 

#49 Would you prefer a cabin in the mountains or a beach house?

Cabin folk is an entirely different breed than beach goers. Talk about what makes one more attractive than the other. Do they like a remote location and the peacefulness of a forest or the sound of ocean waves and a beachside cocktail? 

#50 Would you instead open an online business or a storefront? 

If either of you has an entrepreneurial spirit, this topic allows you to dive into the benefits and drawbacks of each type of sales. A more extroverted person may crave the daily interactions with customers, while a nomadic spirit may love the idea of a small business they can run from anywhere. 

#51 Would you rather be able to teleport anywhere or be able to rewind time?

Both could have some significant advantages and drawbacks. If you could teleport, where would you go? What would they change in the past if they choose to rewind time? What period would they visit? 

#52 Would you rather never have to pay for food at restaurants or have unlimited first-class flights for the rest of your life? 

Free food or unlimited travel is a tough choice. Follow up with questions about your favorite restaurants or dream destinations.  

#53 Would you rather have 12 cats or 12 dogs?

“Cat people” and “dog people” are undeniably wired differently. If you had to choose a dozen of one or the other, which would it be? What breeds and why? 

#54 Would you instead drive a pickup truck or a sports car?

You may already be able to guess their answer based on their clothing and personality. After all, the care someone drives is yet another means of self-expression. Try matching each other to a specific vehicle make, model, and color for a playful twist. Are they more of a 4×4 Ford pick-up truck with a lift kit or a shiny new BMW with rhinestone license plates? 

#55 Would you instead be stuck in a heat wave or a snow storm?

You can always put on more layers, but you can’t take them off. But a heat wave near a body of water may not seem so bad. How someone reacts to hypothetical extreme weather could say something about their adaptability to less-than-ideal situations. You can also discuss the weather extremes of each person’s hometown. 

Random and Interesting First Date Conversation Topics

Spice things up with questions your date may have never been asked before. These topics combine curiosity with the element of surprise. 

#56 If you could give me a tour of your hometown, where would you take me? 

Instead of asking, “where are you from?” you can find out more about your date’s hometown with this unique figurative situation. 

#57 Who is the most bizarre person you’ve ever met?

This can bring up a hilarious story or some weird memories. Either way, you can discover what your date considers “out there.” 

#58 What’s the strangest way you’ve become friends with someone?

Friendships can take off from social media, random coffee shop meetings, or bumping into someone in a public place. 

#59 How would you survive a zombie apocalypse? 

Maybe you’ll find out your date has some secret skills you’d want on your team. 

#60 If you could remove one animal or insect from the Earth, which would it be? 

Cockroaches, mosquitoes, ticks, or snakes? Laugh over your mutual disdain for the nastiest creatures. 

#61 What drives you crazy about people regularly?

Psychologists have found surprising evidence that people build stronger connections through mutual dislikes. You can relate to some shared pet peeves without going down a negative rabbit hole. Who doesn’t despise bad drivers or people who leave a big mess behind them?

#62 What is your weirdest scar, and how did you get it?

Maybe they tried to sneak out of the house as a kid or once almost cut their finger off while chopping an onion. Learn about your date’s weird or random scar and its story.

#63 What is the dumbest thing you did as a teenager?

It’s always a good sign if someone can laugh about their shortcomings. After all, everyone makes some youthful mistakes. 

#64 What’s your favorite way to be active? 

Even if you’re into running or yoga, you may not want overtly ask if someone works out regularly. Instead, gracefully open the topic of activity with this strategic question. 

#65 What was the last event you bought a ticket for?

The concert, sports game, conference, or festival? If they’re willing to pay for a ticket, they’re probably interested in the music, sport, or topic. Their answer could be a great future date invitation idea. 

#66 If you could improve one thing about the human body, what would it be?

They’ve probably never thought about it before. Maybe you’d change the need to sleep for 8 hours a day— what a waste of time! You can dig into topics about optimizing health and wellness or the potential existence of a “fountain of youth.” 

#67 If you had a pet tiger, what would you name it?

OK, this one is totally out of the left field. But at least you’ll get some points for being imaginative. 

#68 Have you ever wanted to live van life?

The #vanlife and #tinyhome craze can bring out someone’s inner vagabond. See if your date has ever fantasized about living on the road or if they couldn’t stand being in such a small space. 

#69 What’s the most ridiculous fashion trend you have ever tried to follow?

Nineties gauchos or Y2K gel-tipped hair? What was a trend you followed that would look hilarious today? Bonus points if you have a photo. 

Deep Things to Talk About on a First Date

Once you’ve surpassed small-talk and (hopefully), found a steady connection between you and your date, consider asking some more profound questions related to their perspectives on life. These topics open up deeper conversation topics without being too invasive: 

#70 What assumptions do people often make about you that are wrong?

There is always more than meets the eye! People are typically aware of the assumptions or judgments people regularly make about them. You can laugh together about the things people tend to get wrong about you based on your appearance. 

#71 What is the most beautiful place you’ve ever visited?

Beauty is in the eye of the beholder. Whether it’s a waterfall, a mountaintop, or a coastline, you’re sure to learn something about your date’s favorite scenery. 

#72 What are you looking for in a partner?

You might as well cut to the chase at some point during a date. Casually find out more about what this person is looking for regarding a relationship. Do you fit the bill? Are your priorities aligned? 

#73 What’s on your bucket list?

Everyone has that far-out thing they want to do before they die. Talk about the top items on each of your bucket lists

#74 What takes your breath away?

 It sounds romantic and may inspire discussions about life lessons, new experiences, poetry, and art. You can also consider going the humorous route: a hard workout will knock the wind out of you.

#75 What is one of your favorite quotes about life?

An inspirational quote can hold a lot of insights into what motivates somebody. 

#76 What qualities do you look for in a best friend?

The qualities people search for in friendship say a lot about a person’s values. You can talk about your closest friends and what you like most about them.   

#77 What was the most important lesson you learned in the past year?

Your date’s answer is like a sneak peek into their mindset about growth, challenges, and change. Extracting a lesson from life’s high or low points shows maturity and self-reflection.

#78 How do you imagine your life 10 years from now?

Not everyone has a big plan for their life, but the response to this question can provide clues about your compatibility. Discuss concrete visions like long-term goals, career aspirations, health milestones, family desires, and locations to live or travel. Don’t get too ahead— it’s only the first date! 

#79 What do you want to improve about yourself? 

An eye toward self-improvement is a major “green flag” for a potential partner. It’s also an opportunity to share your specific interests in personal growth. Whether you’re working on your fitness, listening skills, or reading more books, this topic can be a great indicator of self-awareness and a growth mindset

#80 Do you enjoy your alone time? How do you spend it?

Spending time alone is linked to higher confidence, more creativity, and higher emotional intelligence. Solo hobbies make for an exciting discussion. Plus, your dates’ response could be a 

#81 How do you define success in your life? 

Success is a tricky topic that everyone looks at differently. Maybe they’ll go the financial route, or perhaps they’re more geared toward fulfillment and freedom. Talk about different philosophies on success and who you consider to be successful. 

#82 If you could impart one piece of advice to your younger self, what would it be? 

Even if you were younger, you wouldn’t have listened. Sharing a piece of advice is an excellent insight into how much someone has grown and changed over the years. 

Key Takeaways: Great First Dates are all About Interesting, Balanced Conversations 

Don’t get hung up on the details if you feel uneasy about a first date or have sat through some agonizing silences. Take a few conversation ideas and expand on them in a way that feels natural to you. Remember, the best first date conversation starters are:

  • Inquisitive: People love to talk about themselves. When in doubt, ask more questions! 
  • Attractive: Avoid the boring “how about this weather?” or “what do you do for a living?” Explore conversation starters that dig more into opinions, character traits, and interests. 
  • Balanced: A first date shouldn’t feel like an intimidating interview or a lengthy sales pitch. Find a balance between how many questions you ask and how often you respond. Aim to listen to your date around 70% of the time and talk about yourself around 30% of the time. 
  • Lighthearted: To maintain playfulness and fun, try not to dive into topics that are too invasive. Keep your conversations lighthearted and focused on the positive. 

Coming up with things to discuss on a date is not always easy. Fortunately, anyone can learn better conversation skills by utilizing psychological tricks and time-tested conversation starters.

Here are 30 Ways to Effortlessly Start a Conversation with a Guy or 25 Ways to Masterfully Make Conversations with Girls.  

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