First dates can be exciting and fun, but let’s be honest: they can also be awkward and intimidating. The goal is to click with this person and possibly meet someone special, but what if you run out of topics to discuss within the first few minutes of the date? In this article, we will go over a list of first-date conversation starters.
What if, in your efforts to keep the conversation going, it begins to feel like a job interview? There is good news! You no longer have to deal with those dreaded awkward silences or uncomfortable pauses because we’ve come up with some great first-date conversation starters. They will not only improve your first date and help you connect with each other, but they will also increase your chances of getting date number two.
First Date Conversation Starters
If there’s one thing that can ruin a first date and guarantee a woman’s first impression of you is a negative one, it’s bad conversation. You’ll need icebreakers, light-hearted questions, questions that elicit banter, laughter, and thought, as well as questions that delve a little deeper and go beyond the surface.
We’ve compiled a list of first-date conversation starters that do all of these things to save you from endless awkward silences. They’re also backed by experts who know what they’re talking about. Continue reading for first-date conversation starters to try on your next romantic evening.
1. WHERE WOULD YOU GO IF YOU COULD HOP ON A PLANE RIGHT NOW?
Who doesn’t enjoy traveling? Hermits, to be precise. If she despises planes and road trips, or if she has no desire to leave her hometown ever, this is a good indicator of her ambitions and desires (or lack thereof). Otherwise, Jones says, this question will pique her interest, and you’ll learn what she finds most appealing. It encourages a healthy back-and-forth between the two of you.
2. IS THERE ANYTHING ABOUT YOU THAT I WOULDN’T GUESS?
“Because it’s a little mischievous and flirtatious,” Jones says, “it’s a great icebreaker.” “It’s a sign that you want to know her beyond the surface level, while still allowing her the freedom to reveal; what she wants to share and what she doesn’t.”
3. WHAT ARE YOU MOST ENTHUSIASTIC ABOUT?
This question gives you an idea of what she’s passionate about and whether she’s spirited and heartfelt. It’s also a great way to see if her level of passion matches yours, according to Jones.
4. EXPLAIN YOUR DREAM JOB.
“This is an excellent question because a dream job combines meaning, passion, and lifestyle,” Jones says. Even better, her reason will be extremely telling. Is it the money, the impact, or the pleasure? Every one of these explanations reveals something about her personality.
5. WHAT THINGS MAKE YOU LAUGH OUT LOUD?
If things become awkward or serious, change the subject to something lighter. Everyone enjoys a good laugh, and talking about the things that make you both laugh—cheesy pickup lines, a favorite YouTube video—gets the conversation going… and both of you laughing. Jones believes that a lot of laughter on a first date is a good sign.
6. WHAT WOULD YOU DO ALL DAY IF WORK WAS NO LONGER AN OPTION AND YOU HAD PLENTY OF MONEY?
According to Jones, these first-date conversation starters can bring a light, playful, untethered feeling into your mix of questions. “It’s also interesting to hear anyone’s response,” she adds. If she watches every television show ever made, and you’re an active guy who can’t stand being indoors, you might not be a good match.
7. WHAT ARE YOUR FAVORITES ABOUT LIVING HERE?
This question is interesting whether you’re new to a city or have lived there for a long time. “You get to talk about local places she likes, see what you have in common, bond over people and culture, and explain why you moved to the area in the first place,” Jones says. Even better: “Many second-date ideas can come from this question.”
8. WHAT HAS BEEN THE MOST IMPORTANT OR BEST YEAR OF YOUR LIFE YET?
This is a great fallback if you want the conversation to become more reflective, thoughtful, and meaningful. “You get to hear not only about her life story but also the snippet that’s most meaningful and important to her,” Jones explains.
9. WHAT IS THE ONE THING YOU DID AS A CHILD THAT YOU MISS THE MOST NOW?
With this conversation starter, she’ll feel a little nostalgic. It’s amusing. And who knows, you might have gone to the same camp or vacation spot every summer. “It’s interesting to see what you might have shared as kids,” Jones says.
10. WITH WHOM DO YOU CONNECT THE MOST?
You’ll learn about her lifelong friends and family. Good: You can tell if she has a close relationship with her parents or siblings. Bad: You can tell if she’s still mad at an ex. “The five people we spend the most time with shape us the most; her relationship with any of her closest friends and family members tells you a lot about her,” Jones says.
11. WHAT DID YOU DO WITH YOUR DAY?
Are you waiting to be seated or for your waiter to arrive? Break the ice with a simple, direct question like this. “You get a peek into her day, her job responsibilities, how she handles stress, her energy level, tone, and how she spends her time,” Jones says. Those small details, as well as what she chooses to focus on, whether good or bad, reveal a lot about her personality.
12. WOULD YOU GO ON A CROSS-COUNTRY DRIVE?
This may appear odd and specific, but how she likes to travel can be just as telling as to where she likes to travel. Is she only staying in five-star hotels? Is she interested in environmentally friendly locations? Also, is she interested in camping and RVing? All of these options provide “insight into her lifestyle, taste, and knowledge of other cultures.” Sullivan claims.
13. WHAT IS THE FIRST ATTRACTION YOU SHOULD VISIT IN A NEW CITY?
Some people believe that you never truly know someone until you travel with them. You’re unlikely to travel on a first date, but this question (when combined with the one above) can provide a wealth of information about her personal life. “This opens the door for discussion about history, religious perspectives, art, and culture,” says Sullivan. If she’s into museums and monuments, you can deduce she’s a history buff—or, better yet, ask her if she’s a history buff. Allow one question to lead to the next.
14. WHAT ARE THE FIVE THINGS YOU WANT TO DO BEFORE YOU DIE?
You’ll gain a lot of insight into her life goals and priorities. You can tell if she’s philanthropic, an outdoor enthusiast with a killer bucket list, or anything in between.
15. WHAT IS YOUR FAVORITE COOKED DISH?
“Learn about her culinary skills, what foods she enjoys, if she enjoys healthy cooking, and if she has any favorite restaurants,” says Sullivan. Food is always a safe topic of discussion—and an endless one at that.
16. WHAT ARE YOUR PRIMARY SPORTS?
“If sports are important in your life, this will lead you to a plethora of subtopics,” Sullivan says. Inquire about her favorite sports, favorite teams, and whether or not she played sports in college. Depending on her response, you’ll be able to tell if you’re up for some healthy competition or if you’re rooting for the same teams. And if she doesn’t care, you can decide whether it’s a minor annoyance or a deal-breaker.
17. WHAT ARE SOME OF YOUR FAVORITE TELEVISION SHOWS?
What she likes to watch on a daily basis reflects her interests. Is it true that she only watches educational shows? Is she more interested in news or talk shows? Maybe she is a total reality show junkie? You’ll also learn how much time she spends sitting on the couch.
18. HOW DID YOU SPEND YOUR LAST WEEKEND?
If you want to be compatible with a woman, you should share common interests and hobbies. Inquire as to how she spends her spare time! This gives you an idea of whether she enjoys relaxing or having fun when she’s not at work.
19. WHAT TYPES OF BOOKS DO YOU ENJOY READING?
Is she pursuing self-improvement and reading solely to better herself and her career, or does she read for pleasure? Engage her in a discussion about what inspires her. “This is a good way to learn about her intellectual interests and passions,” says Sullivan.
20. WHO HAS HAD THE MOST INFLUENCE IN YOUR LIFE?
“Rather than asking her how close she is to her family, ask, ‘Who is the most influential person in your life?'” Sullivan claims. “You’ll learn more about her family dynamics and the close relationships she has with her friends as a result of this.”
21. DO YOU STILL CONNECT WITH CHILDHOOD FRIENDS?
Unless she moved around a lot as a kid (which should raise some eyebrows), asking if she still talks to childhood friends will reveal how she values relationships and loyalty.
22. WHAT THREE THINGS WOULD YOU TAKE WITH YOU IF YOU WERE STRANDED ON AN ISLAND?
Taking her by surprise is a good thing as long as your intentions are pure and playful. Despite the oddity of the question, you’ll learn what’s most important to her and the significance of those items.
23. WHICH ANIMAL IS YOUR FAVORITE?
Lighthearted questions like this one can elicit childhood memories for her. It will also tell you if she likes animals. It may appear silly, but if she despises dogs and your Husky is a member of the family. If she has two cats and you are allergic to them, things may not work out.
24. WHAT IS THE LUCKY THING YOU’VE EVER DONE?
Is she an adrenaline junkie or a free spirit? You’ll find out if she’s run with the bulls or climbed a mountain. “This is a great first date conversation for the starter to see how adaptable she is,” Sullivan says. You can also see if your personalities and interests mesh.
25. WHAT IS YOUR MOST VEXING PET PEEVE?
Inquire about the minor irritations that irritate her. “Obviously, you’ll gain an understanding of her temperament,” Sullivan says. But you’ll also be able to break any bad habits that are keeping you from getting a second date.
26. WHAT IS YOUR FAVORITE MOVIE OF ALL TIME?
“Her response will reveal whether she has a dark, goofy, nerdy, romantic, sappy, or quirky side,” says Sullivan. Plus, you won’t be caught off guard if you plan a movie date and end up watching a rom-com.
27. WHAT DO YOU LIKE TO DO IN THE MORNINGS?
Her morning routine may appear to be overly specific, but it is extremely revealing. Does she get up, get ready, and dash to work with only a few minutes to spare? Does she get up, relax, read the newspaper, and then get ready for work? Or does she meditate, go for a six-mile run, shower, and prepare a gourmet breakfast before leaving? These scenarios depict three very different people and personality types.
28. WHAT DO YOU LIKE TO DO ON NIGHTS OUT?
This question, like the previous one, reveals how she spends the majority of her time and whether you’ll enjoy the same activities. On a Saturday night, you may enjoy going out to bars and clubs for karaoke, whereas she would rather binge-watch the latest Netflix series. You’ll know whether you’ll crash early on.
29. CAN YOU TELL ME ABOUT YOUR QUIRKS?
Perhaps she sleeps with the TV on or prefers to eat ice cream with a fork. This allows you to see if she has any endearing… or repulsive… quirks.
30. WHAT IS YOUR FAVORITE SONG/ARTIST/BAND/GENRE OF ALL TIME?
“Asking about her favorite song, band, or artist as a first date conversation starter tells you a lot about her musical taste,” Sullivan says. However, you can branch out and find out what her first concert was and who she’s dying to see; and if the cards fall in your favor, these tidbits of information can turn into a fantastic future date or surprise.
31. WHAT TERRIFIES YOU THE MOST?
This question can be answered in a lighthearted or serious manner. Try them both. Check to see if she still has any childhood fears, such as spiders, darkness, or basements. And ask her what she is most afraid of in life: failing at her job, never having the opportunity to travel, or mending a particular relationship? You’ll see a vulnerable side of her without being overly confrontational.
Funny First Date Conversation Starters
So, if you’re trying to break the ice or just jump-start the conversation on a date, here are the top funny questions for first-date conversation starters that are guaranteed to make them laugh—or, at the very least, pretend to laugh and then buy you a drink for trying.
1. So, you’re married, right?
If you enjoy dry humor, asking your date something absurd will undoubtedly loosen them up and help them better understand you. “Begin with what is funny to you and see if you can connect on that rather than feeling pressured to be funny,” Hoffman advises. “It’s about finding someone who understands and appreciates your sense of humor, rather than trying to entertain them like a clown.”
2. Can you guess what my passive-aggressive coworker sent me today via email?
Having your partner guess what someone said to you allows them to do something and get some attention. It’s all about the back-and-forth.
3. Can I complain about my terrible roommate clogging the sink again if I pay for drinks?
You might not be in the mood to be a flirty rom-com girl happy funny if you’ve had a bad week. Rather than pretending to be #live #laugh #lovinglife, express that you’ve had a long week in a humorous way, such as offering to pay for drinks.
4. Who would you think you are if they only saw your Spotify or Netflix accounts?
It’s exhausting to ask someone to name their favorite bands or movies. Rather than pressuring someone to name their favorites just to pretend you’ve heard of them, ask them about their Spotify/Netflix footprint. Is it a 70-year-old man on vacation in the Florida Keys?
5. Would you rather be famous on TikTok or win a Grammy?
According to Germany, “would you rather” questions often lead to amusing first-date conversation starters. One thing leads to another, and before you know it, you’re both crying and laughing. These questions are a good way to find out what someone is interested in or other interesting facts about them that you might not have discovered otherwise.
6. What is your favorite dad joke?
“Dad jokes are awkward anyway,” Germany says, “so you can both just laugh at yourselves and have fun with it.” “Remember to practice your joke ahead of time so you don’t freeze up on the spot.”
7. What was the first R-rated film you saw? Who kidnapped you?
Inquiring about super-specific aspects of childhood is a great way to gain a broad understanding of how someone was raised and what their family is like. However, making it about something silly, such as an R-rated movie or a song with profanity, keeps it light.
8. What’s a word you’ve spelled incorrectly your entire life?
Were you under the impression that salmon had a hard “L”? Do you pronounce “Parmesan” like “par-me-san”? Hoffman observes that asking about something embarrassing but not overly emotional or traumatic keeps things light and is sure to strengthen your bond.
9. Could you please tell me about your favorite and worst school photos?
“Asking someone to share a funny or embarrassing childhood memory can also be a good one,” Germany says. “The goal isn’t to be a comedian, but to start conversations.”
10. What was your AIM handle?
This is for the millennial generation, you know, the people who didn’t grow up with Instagram. However, if you or your date prefers TikTok over Tumblr, inquire about the most embarrassing thing they’ve ever posted.
11. What was the worst middle school fashion trend you were a part of?
What are frosted tips? Chains and goth pants? Small brows? Extra points for sharing photos.
12. What do you buy in excess but never seem to have enough of?
Chapstick? Socks? White Claw with a Black Cherry? Inquire with your date about what they keep but never seem to find when they need it.
13. What is the most cheesy internet pop psychology advice that actually resonated with you?
Sometimes green juice-drinking lifestyle influencers’ Instagram musings just hit.
14. Does being an influencer sound like a dream come true or a nightmare?
Whether your date is addicted to the internet or still uses a flip phone, asking about influencers is bound to generate some laughs and potentially lead to some interesting conversations.
15. What is the best WiFi name you’ve come across?
The names of WiFi networks range from cheesy to explicit. Inquire about any amusing ones they’ve seen, and you might learn something about their previous neighbors.
16. If your life were an “expectation vs. reality” meme, what two pictures would you choose?
Do people think you’re an extrovert, but all you want to do is live in a small cabin in the woods? Inquiring about it in meme form is a much chillier way of asking “what do people falsely assume about you?”
17. What would your name be if you were an amateur wrestler/D-List superhero?
Ask them to create an entire character, including what they would wear, their motto, and who their adversary would be.
18. What is your favorite karaoke song?
This is a test because it determines whether they (1) enjoy karaoke, (2) enjoy having fun, and (3) choose something by The Chicks.
19. What is a book that you haven’t read but pretend to have read?
What is Infinite Jest? Tell me, what about the Odyssey? We’ve all got one. Inquire about their academic flexing; you might be surprised to learn about which books or classes they fell in love with during their school years.
20. What would your dream vanity license plate look like?
Vanity license plates are a cross between niche hipster cryptic internet humor and actually funny memes that your mother would find amusing. Prepare to howl if you ask them what they want on their plate.
21. Tell me how many hours a day you spend on TikTok.
The new version of astrology compatibility is comparing screen time amounts. Inquire about their favorite pages and what first drew them into the Tok.
22. What is something embarrassing that shouldn’t be?
Can you recite 100 Pi numbers? Did you spend the entire fourth grade dressed like Avril Lavigne? Do you know every word to every Imagine Dragons song? A good first date conversation starters are to ask them about something they do that they are not ashamed of.
23. What kind of grocery shopper are you?
There is a significant distinction between a list maker and an impulse buyer. Don’t even get me started on the people who don’t walk up and down every aisle.
24. What is the dumbest thing you’ve ever done to hurt yourself?
If your date is naturally clumsy, you’re bound to get some amusing stories out of him or her. Even if they’re a well-balanced babe, they might tell you a funny story about tripping in T-ball.
25. What was something you believed as a child for a very long time?
Did you think dishwashers were frightening? Wasn’t it true that OJ and orange juice were two different things? Share your own amusing memory and ask for theirs. “Self-deprecating humor frequently elicits laughter because it demonstrates self-awareness and is relatable,” Hoffman says. “We can use nostalgia as a bonding tool when we tap into a story from the past.”
26. What was the dumbest lie you ever told as a child?
Twisted kid logic will undoubtedly make you both laugh. Inquire about a time when they claimed their cat made a mess in the kitchen or that they were late for chemistry class because they got lost in the woods on their way to school.
27. What is the oddest thing about you that most people wouldn’t notice just by looking at you?
Perhaps you sleep with your socks on. Perhaps you, like Camila Cabello, eat a banana with every meal. Inquiring about their quirks “cuts through the boring date script and gets to the heart of who they are, and may make them giggle in the process,” Hoffman says.
28. How long do you put off getting up to pee when you’re watching a good TV show?
A personal but amusing question for first-date conversation starters (such as the one about pee habits) is disarming and will undoubtedly cause you both to bond. If you’re not interested in potty talk, inquire as to how long it takes them to grab the remote or go get a drink.
29. What is the most disgusting food thing you’ve ever done?
Did you eat something off the floor? Have you ever left takeout on the table overnight and then finished it in the morning? You’ll both be giggling as you spill the tea on your food history.
30. Have you ever had sexual feelings for a cartoon character?
Mulan’s guy could totally get it. Inquire about their favorite animated guilty pleasures and which cartoons they enjoy watching.
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Good First Date Conversation Starters
Do you cringe or smile when you hear the words “first date”? First dates can be awkward, nerve-wracking, exciting, disastrous, or wonderful for a variety of reasons. The first impression you each make, as well as how well you and the other person connect, play a significant role in this distinction.
Here is a list of conversation starters for first dates:
1. What distinguishes you?
It may seem obvious, but getting someone to talk about themselves is the simplest way to connect with them. Inquire about their hobbies and interests… do they enjoy sports, painting, spending time outside, reading, or dancing? Maybe you’ll find something you both enjoy doing, and if the date goes well, it could be a good idea for another date later on.
2. Can you tell me some random fun facts about yourself?
Finding out something interesting about another person that would not normally come up in casual conversation is a fun way to get to know them. You’ve just learned about their interests; now ask if they’ve ever had the opportunity to do something crazy or out of the ordinary, such as appear on television.
3. What is something you’d like to learn or something you wish you were better at?
This is a subset of the more general question, “What are your hopes and dreams?” Asking them if there is anything specific they’ve been wanting to learn or practice elevates the conversation to a new level.
4. Would You Rather…?
“Would you rather…?” questions are a good go-to, especially as conversation starters on a first date. They make excellent icebreaker questions because they can be answered by both of you and can be as superficial, deep, or silly as you want. Would you prefer… Should I go to the beach or the mountains? Do you want to spend the rest of your life drinking only coffee or soda? Get stuck on a roller coaster or become horribly disoriented in a massive theme park?
5. Do You Have Any Good Jokes?
If they can share something that made them laugh, you will quickly get a sense of their sense of humor. Furthermore, giggling together at a stupid “dad joke” is another way to break the ice and make you feel more at ease with the other person.
6. Is There Anything That Annoys You?
Everybody has a pet peeve. Discuss the things that irritate you. Inquire about your date’s problems. Are they generally relaxed and easygoing, or are they tense and easily stressed? Finding out each other’s pet peeves can help you gain a better understanding of some of the things that make people tick, and it’s a good way to start being open and honest with each other right away.
7. What is the most embarrassing thing that has happened to you that you can recall?
Check to see if they’re willing to share some of their most embarrassing moments. Talking about our awkward moments demonstrates humility, vulnerability, and a sense of humor; is it important to you that your date can occasionally laugh at themselves?
8. What is your favorite place on the planet?
Is there a favorite vacation spot for them? Is there a cool hiking trail hidden behind the river that they’re aware of? Tell me, is there a secret location where they can relax, unwind, and escape the world? These questions allow others to see into our “happy place” and see what kinds of settings make us feel most like ourselves.
9. Who are the important people in your life?
Inquire about your date’s siblings, best friends, grandparents, or even their pets. Pay attention to how someone talks about other people to get a sense of their personality. This question also reveals who has had the greatest influence on your date’s life and who has helped shape them into the person they are today.
Listening to someone describe someone they love is one of my favorite things in the world; watching that little light catch in someone’s eyes when they tell me a story about a friend or loved one is one of my favorite things in the world.
10. What is something you’re particularly proud of?
Aside from their humility, are they proud of their accomplishments? Do they call their mother as soon as they learn of a new promotion? Inquire as to which decisions they have made that they are truly pleased with. When was the last time they won an award? This will assist you in determining some of the things they truly value as well as some of the things they have worked hard for.
Best First Date Conversation Starters
Continue reading to learn about the best first-date conversation starters to try on your next romantic evening.
1. Speak about your origins.
When you and your date share your childhood experiences, it can strengthen your bond and help you learn more about each other. Whether you come from similar or dissimilar backgrounds, discussing where you’re from, your family life and details from your childhood can help reveal new insights about one another. For example, if you’re the youngest of four children and they’re only children. You continued to watch the same shows, play the same video games, and attend the same summer camps.
2. Talk about your favorite movies, television shows, and books.
There is no shortage of streaming services in today’s world, with Netflix, Hulu, Amazon Prime, and Audible. or access to movies, television shows, or literature Keeping this in mind, discussing the various TV shows you’re watching, dishing on must-see movies, and telling them about your all-time favorite books can help keep the conversation flowing while you and your date reveal more about your respective personalities.
For example, if you’re a fan of Stranger Things, can’t get enough of The Marvelous Mrs. Maisel, or have read everything by J.K. Rowling, these can be excellent starting points for first-date conversation starters. It can help you see if there are any sparks between you and your date as you discuss what’s binge-worthy and what’s hot right now.
3. Be Open About Your Hobbies
When you’re on a first date, it’s important to discuss your hobbies, passions, and what makes you who you are. If you’re a guitarist, yogi, or die-hard football fan, talking about your hobbies and interests can help you and your date connect on a deeper level.
By discussing what you enjoy doing for fun, you are teaching your date more about yourself while also opening the door for them to learn more about you. You’ll discover their preferences while also determining how much free time they have and how they spend it.
4. Hold a Travel-Related Conversation
Do you consider yourself a jet-setter, in terms of hobbies? Do you want to go to Greece someday? Have you recently returned from a trip to Hawaii? Talking about travel is one of the best first-date conversation starters because it allows you to share your travel experiences (both good and bad), open up about places you’d like to visit one day and discover any potential incompatibilities. As you open up about your ideal types of vacations and favorite travel destinations, you and your date can learn more about each other’s interests and passions.
5. Talk About Your Favorite Music
Because you can learn a lot about a person by discussing their favorite music, it’s a great conversation topic for a first date. While you and your date may discover that you and your date enjoy the same types of music and have even seen the same bands or festivals live, you can also broaden your own music repertoire as you learn about the genres and bands that your date enjoys.
A first date can be a great way to get recommendations for new bands, and talking about music and concerts can help the two of you bond. You can talk about the best (and worst) shows you’ve ever seen or the different artists you’d like to see live.
6. Talk About Your Goals
What do you want to be in five years? What about ten years? When it comes to the big questions in life, being able to open up about your goals, hopes, and desires on a first date can be a great way to get to know someone better.
Your objectives don’t have to be strictly professional; the important thing is to express what you want to achieve, whether it’s learning to play the guitar or mastering French cooking. as this can assist your date in learning more about your interests and priorities
7. Discuss Food
Because first dates aren’t always about food, talking about it can be a great way to set the tone (or set the table) for a second date. You and your date can discuss the best places in town for a bite, as well as the best meal you’ve ever had, as you open up about your favorite restaurants, cuisines, and bakeries.
Conclusion
So, whether you’re completely terrified of that first date with your crush or just need some ideas for ways to break the ice with a Tinder match you’re meeting for the first time, these first-date conversation starters should definitely help get you started. These are some positive ways to become acquainted with someone and reveal the nature of your relationship with them. You’ll never know unless you ask!
Frequently Asked Questions
What are good topics to talk about?
They’re great for after you’ve made the friendly introductory small talk and feel like you’ve connected with the person.
Time to relax. What do you like to do in your spare time? … Music. What kind of music do you like? … Movies. What kinds of movies do you like to watch? … Food…. Books…. Television…. Travel…. Hobbies.
What do you talk about on a date?
Where would you go if you could hop on a plane right now? … Where exactly is ‘home’? … What is the most delicious meal you’ve ever had? … Did you have any nicknames as a kid? …
What were you like when you were a kid? …
What is it about you that I wouldn’t guess? … What items are on your bucket list?
