Conversation Starters | Questions and Answers
Hint: Travel
If you could hop on a plane right now, where would you go?
Who doesn't love to travel? Hermits, that's who. If she hates planes, road trips, or has no desire to leave her hometown ever, that's a good indicator of her ambitions and desires (or lackthereof). Otherwise, this question will excite her and you'll learn what's most appealing to her, Jones says. It promotes a good back-and-forth between the two of you.
Hint: Guess
What's something I wouldn't guess about you?
"This is a great ice-breaker because it's a little mischievous and flirtatious," Jones says. "It's a sign you'd like to know her beyond surface level, while still giving her the freedom to reveal what she wants to share—and doesn't."
Hint: Passion
What are you most passionate about?
This question lets you get a sense of what she feels strongly about and whether she's spirited and heartfelt. It's also the perfect way to gauge whether her level of passion is compatible with yours, Jones says.
Hint: Dream job
What's your dream job?
This is a great query because a dream job merges meaning, passion, and lifestyle," Jones explains. Better yet, her reason will be incredibly telling. Is it the money, the impact, the enjoyment? Each of these explanations reveals something about her character.
Hint: Laugh
What sort of things make you laugh out loud?
If things get a bit awkward or serious, divert to a more carefree topic. Everyone loves to laugh, and talking about the things that make you both fall into a fit—cheesy pickup lines, dad jokes, a particular YouTube flick—gets the conversation flowing... and both of you laughing. Lots of laughter on a first date is a great sign, Jones says.
Hint: Lots of $$, no work
If work was no longer an option and you had plenty of money, what would you do all day?
This conversation starter can bring a light, playful, untethered feeling into your mix of questions, Jones says. "It's also fascinating to hear anyone's answer," she adds. If she'd watch every television series ever created, and you're an active guy who can't stand to be indoors, well, that shows you might not be super compatible.
Hint: Living here
What do you like most about living here?
This question rocks whether you're new to a city or you've lived there for years. "You get to talk about local places she likes, see what you have in common, bond over the people, culture, and why you moved to the area in the first place," Jones says. Better yet: "Many second date ideas can be born from this question."
Hint: best year
What's been the most significant or best year of your life so far?
If you want the conversation to become a bit reflective, thoughtful, and meaningful, this is a great fall-back. "Not only do you get to hear about her life story, but the snippet that's most meaningful and important to her," Jones explains.
Hint: childhood activity
What's one thing you did as a kid that you miss most today?
She'll get a little reminiscent with this conversation starter. It's playful. And who knows, maybe you went to the same camp or vacation spot each summer. "It's fun to see what you might have had in common as kids," Jones says.
Hint: Talk
Who do you talk to the most?
You'll learn about the people closest to her in life. Good: You can see if she has a tight bond with her parents or siblings. Bad: You can see if she's still hung up on an ex. "The five people we're around the most, shape us the most; her relationship to any one of her closest friends and family members tell you a lot about her," Jones says.
Hint: day
How did you spend your day?
Waiting to be seated at your table or for your waiter to arrive? Break the ice with a simple, straight-forward question like this. "You get a glimpse into her day, her job responsibilities, how she deals with stress, her energy level, tone, and how she spends her time," Jones says. Those small details and what she chooses to focus on—whether good or bad—clue you in on her personality big time.
Hint: 5 things
What are 5 things you want to accomplish before you kick the bucket?
You'll get major insight on her goals and priorities in life. You can gauge whether she's philanthropic, an outdoor buff with a killer bucket list, and everything in between.
Hint: Cook
What is your favorite dish to cook?
"Learn about her culinary skills, what food she likes, if she's into healthy cooking, and has any favorite restaurants, Sullivan says. Food is always a safe topic of conversation—and an endless one, too.
Hint: TV
What are some of your favorite TV shows?
Her interests are reflected in what she likes to watch on a daily basis. Does she only watch educational shows? Is she all about news or talk shows? Is she an absolute reality show junkie? You'll also find out how much time she spends on the couch.
Hint: Last weekend
What did you do last weekend?
If you're going to be compatible with a woman, you need to have common habits and hobbies. Ask her how she spends her free time! From this, you get a sense of whether she enjoys relaxing or letting loose when she's away from work.
Hint: Type of books
What kind of books do you like to read?
Is she on the road to self-improvement and solely reads to better herself and her career, or does she read for pleasure? Get into a conversation about what inspires her. "This is a good way to know what her intellectual interests and passions are," Sullivan says.
Hint: childhood friends
Do you still keep in touch with childhood friends?
Unless she moved around a lot as a kid (this should spark questions, too), asking whether she still talks to friends from childhood will reveal how she values relationships and loyalty.
Hint: island
If you were stranded on an island and could take three things with you, what would they be?
Catching her off guard is a good thing so long as your intentions are innocent and playful. Despite the quirkiness of this question, you'll find out what's most valuable to her and the significance of those items.
Hint: Spontaneous
What's the most spontaneous thing you've ever done?
Is she a thrill-seeker or a free spirit? You'll find out if she's been running with bulls or scaled a mountain. "This is a great question to see how flexible she is," Sullivan explains. You can see if your personalities and interests jive, too.
Hint: pet peeve
What is your biggest pet peeve?
Ask about the little things that drive her nuts. "Obviously you'll get an insight on her temperament," Sullivan says. But you'll also be able to reign in any bad habits that might prevent you from nabbing a second date.
Hint: all-time movie
What's your all-time favorite movie?
"Her answer will reveal whether she has a dark, goofy, nerdy, romantic, sappy, or quirky side," Sullivan says. Plus, you won't be blind-sided if you make a movie date and you're stuck sitting through a rom-com.
Hint: mornings
How do you like to spend your mornings?
It might seem super particular, but her morning routine is hugely revealing. Does she wake up, get ready, and rush to work with minutes to spare? Does she wake up, lounge around, read a newspaper, then get ready for work? Or does she meditate, go for a six-mile run, shower, and make a gourmet breakfast before heading out the door? These scenarios are snapshots of three incredibly different people and personality types.
Hint: nights
How do you like to spend your evenings?
Like the previous question, this one clues you in on how she spends most of her time and whether you'll enjoy the same activities. You may love going out to bars and clubs for karaoke on a Saturday night while she'd rather binge-watch the latest Netflix series. You'll see early on whether you'll clash.
Hint: quirks
What are your quirks?
Maybe she leaves the TV on when she sleeps or likes to eat ice cream with a fork. This gives you a chance to see if she has any quirks that are endearing... or a turn off.
Hint: afraid
What are you most afraid of?
Childhood fear vs. Afraid in life
This question can go the trivial or serious route. Try both. See what childhood fear she still has: Maybe she's terrified of spiders, darkness, and basements. And ask what she's most afraid of in life: Is she afraid of failing in her job, never getting the opportunity to travel, mending a particular relationship? You'll see a vulnerable side of her without being too forward.
Hint: family
Tell me about your family.
Yes, this is a popular first-date question, but for good reason. Go ahead and ask the basic questions about how many siblings she has and how big her extended family is and let the answers lead to deeper, more meaningful ones. It shows you care and are invested in learning who she is from her roots and where she came from.
Hint: better at
What do you wish you were better at?
Ask her what skills she wants to acquire or hone in her career and life in general. If she's ambitious, that can be a major turn on. It'll also show you she's humble and doesn't hold herself too high if she points out some areas she wants to improve.
Hint: worst pickup line
What's the worst pickup line you've ever heard/dished out?
The experts agree: There's nothing wrong with getting a little flirtacious on a first date. Ask her for some of the worst pickup lines she's heard. You'll get some laughs and can try some cheesy ones out on one another. A little banter is a good sign that your humor is in sync.
Hint: nicknames
Did you have any nicknames growing up? Now?
You'll get her laughing with this one. Sure, it might be a little embarrassing, but the stories behind the nickname will make for perfect, light-hearted conversation.
Hint: embarrassing
What's the most embarrassing thing that's ever happened to you?
Share a funny story at your own expense first. It'll show her you have a sense of humor and can laugh at yourself. Then, she'll be more inclined to do the same.
Hint: hidden talents
Do you have any hidden talents?
Maybe she's a classically trained pianist or was a champion cup stacker in her youth. When you ask the right questions—even ones as simple as this—it can unveil a goldmine of information.
Hint: talent wish had
What talent do you wish you had?
See what talents she admires. If she's always yearning to learn something new, it shows she's inquisitive. It can also open the idea of trying something new together—like cooking—on a second date.
If you could hop on a plane right now, where would you go?
Who doesn't love to travel? Hermits, that's who. If she hates planes, road trips, or has no desire to leave her hometown ever, that's a good indicator of her ambitions and desires (or lackthereof). Otherwise, this question will excite her and you'll learn what's most appealing to her, Jones says. It promotes a good back-and-forth between the two of you.
Hint: Guess
What's something I wouldn't guess about you?
"This is a great ice-breaker because it's a little mischievous and flirtatious," Jones says. "It's a sign you'd like to know her beyond surface level, while still giving her the freedom to reveal what she wants to share—and doesn't."
Hint: Passion
What are you most passionate about?
This question lets you get a sense of what she feels strongly about and whether she's spirited and heartfelt. It's also the perfect way to gauge whether her level of passion is compatible with yours, Jones says.
Hint: Dream job
What's your dream job?
This is a great query because a dream job merges meaning, passion, and lifestyle," Jones explains. Better yet, her reason will be incredibly telling. Is it the money, the impact, the enjoyment? Each of these explanations reveals something about her character.
Hint: Laugh
What sort of things make you laugh out loud?
If things get a bit awkward or serious, divert to a more carefree topic. Everyone loves to laugh, and talking about the things that make you both fall into a fit—cheesy pickup lines, dad jokes, a particular YouTube flick—gets the conversation flowing... and both of you laughing. Lots of laughter on a first date is a great sign, Jones says.
Hint: Lots of $$, no work
If work was no longer an option and you had plenty of money, what would you do all day?
This conversation starter can bring a light, playful, untethered feeling into your mix of questions, Jones says. "It's also fascinating to hear anyone's answer," she adds. If she'd watch every television series ever created, and you're an active guy who can't stand to be indoors, well, that shows you might not be super compatible.
Hint: Living here
What do you like most about living here?
This question rocks whether you're new to a city or you've lived there for years. "You get to talk about local places she likes, see what you have in common, bond over the people, culture, and why you moved to the area in the first place," Jones says. Better yet: "Many second date ideas can be born from this question."
Hint: best year
What's been the most significant or best year of your life so far?
If you want the conversation to become a bit reflective, thoughtful, and meaningful, this is a great fall-back. "Not only do you get to hear about her life story, but the snippet that's most meaningful and important to her," Jones explains.
Hint: childhood activity
What's one thing you did as a kid that you miss most today?
She'll get a little reminiscent with this conversation starter. It's playful. And who knows, maybe you went to the same camp or vacation spot each summer. "It's fun to see what you might have had in common as kids," Jones says.
Hint: Talk
Who do you talk to the most?
You'll learn about the people closest to her in life. Good: You can see if she has a tight bond with her parents or siblings. Bad: You can see if she's still hung up on an ex. "The five people we're around the most, shape us the most; her relationship to any one of her closest friends and family members tell you a lot about her," Jones says.
Hint: day
How did you spend your day?
Waiting to be seated at your table or for your waiter to arrive? Break the ice with a simple, straight-forward question like this. "You get a glimpse into her day, her job responsibilities, how she deals with stress, her energy level, tone, and how she spends her time," Jones says. Those small details and what she chooses to focus on—whether good or bad—clue you in on her personality big time.
Hint: 5 things
What are 5 things you want to accomplish before you kick the bucket?
You'll get major insight on her goals and priorities in life. You can gauge whether she's philanthropic, an outdoor buff with a killer bucket list, and everything in between.
Hint: Cook
What is your favorite dish to cook?
"Learn about her culinary skills, what food she likes, if she's into healthy cooking, and has any favorite restaurants, Sullivan says. Food is always a safe topic of conversation—and an endless one, too.
Hint: TV
What are some of your favorite TV shows?
Her interests are reflected in what she likes to watch on a daily basis. Does she only watch educational shows? Is she all about news or talk shows? Is she an absolute reality show junkie? You'll also find out how much time she spends on the couch.
Hint: Last weekend
What did you do last weekend?
If you're going to be compatible with a woman, you need to have common habits and hobbies. Ask her how she spends her free time! From this, you get a sense of whether she enjoys relaxing or letting loose when she's away from work.
Hint: Type of books
What kind of books do you like to read?
Is she on the road to self-improvement and solely reads to better herself and her career, or does she read for pleasure? Get into a conversation about what inspires her. "This is a good way to know what her intellectual interests and passions are," Sullivan says.
Hint: childhood friends
Do you still keep in touch with childhood friends?
Unless she moved around a lot as a kid (this should spark questions, too), asking whether she still talks to friends from childhood will reveal how she values relationships and loyalty.
Hint: island
If you were stranded on an island and could take three things with you, what would they be?
Catching her off guard is a good thing so long as your intentions are innocent and playful. Despite the quirkiness of this question, you'll find out what's most valuable to her and the significance of those items.
Hint: Spontaneous
What's the most spontaneous thing you've ever done?
Is she a thrill-seeker or a free spirit? You'll find out if she's been running with bulls or scaled a mountain. "This is a great question to see how flexible she is," Sullivan explains. You can see if your personalities and interests jive, too.
Hint: pet peeve
What is your biggest pet peeve?
Ask about the little things that drive her nuts. "Obviously you'll get an insight on her temperament," Sullivan says. But you'll also be able to reign in any bad habits that might prevent you from nabbing a second date.
Hint: all-time movie
What's your all-time favorite movie?
"Her answer will reveal whether she has a dark, goofy, nerdy, romantic, sappy, or quirky side," Sullivan says. Plus, you won't be blind-sided if you make a movie date and you're stuck sitting through a rom-com.
Hint: mornings
How do you like to spend your mornings?
It might seem super particular, but her morning routine is hugely revealing. Does she wake up, get ready, and rush to work with minutes to spare? Does she wake up, lounge around, read a newspaper, then get ready for work? Or does she meditate, go for a six-mile run, shower, and make a gourmet breakfast before heading out the door? These scenarios are snapshots of three incredibly different people and personality types.
Hint: nights
How do you like to spend your evenings?
Like the previous question, this one clues you in on how she spends most of her time and whether you'll enjoy the same activities. You may love going out to bars and clubs for karaoke on a Saturday night while she'd rather binge-watch the latest Netflix series. You'll see early on whether you'll clash.
Hint: quirks
What are your quirks?
Maybe she leaves the TV on when she sleeps or likes to eat ice cream with a fork. This gives you a chance to see if she has any quirks that are endearing... or a turn off.
Hint: afraid
What are you most afraid of?
Childhood fear vs. Afraid in life
This question can go the trivial or serious route. Try both. See what childhood fear she still has: Maybe she's terrified of spiders, darkness, and basements. And ask what she's most afraid of in life: Is she afraid of failing in her job, never getting the opportunity to travel, mending a particular relationship? You'll see a vulnerable side of her without being too forward.
Hint: family
Tell me about your family.
Yes, this is a popular first-date question, but for good reason. Go ahead and ask the basic questions about how many siblings she has and how big her extended family is and let the answers lead to deeper, more meaningful ones. It shows you care and are invested in learning who she is from her roots and where she came from.
Hint: better at
What do you wish you were better at?
Ask her what skills she wants to acquire or hone in her career and life in general. If she's ambitious, that can be a major turn on. It'll also show you she's humble and doesn't hold herself too high if she points out some areas she wants to improve.
Hint: worst pickup line
What's the worst pickup line you've ever heard/dished out?
The experts agree: There's nothing wrong with getting a little flirtacious on a first date. Ask her for some of the worst pickup lines she's heard. You'll get some laughs and can try some cheesy ones out on one another. A little banter is a good sign that your humor is in sync.
Hint: nicknames
Did you have any nicknames growing up? Now?
You'll get her laughing with this one. Sure, it might be a little embarrassing, but the stories behind the nickname will make for perfect, light-hearted conversation.
Hint: embarrassing
What's the most embarrassing thing that's ever happened to you?
Share a funny story at your own expense first. It'll show her you have a sense of humor and can laugh at yourself. Then, she'll be more inclined to do the same.
Hint: hidden talents
Do you have any hidden talents?
Maybe she's a classically trained pianist or was a champion cup stacker in her youth. When you ask the right questions—even ones as simple as this—it can unveil a goldmine of information.
Hint: talent wish had
What talent do you wish you had?
See what talents she admires. If she's always yearning to learn something new, it shows she's inquisitive. It can also open the idea of trying something new together—like cooking—on a second date.