50 FIRST DATE

CONVERSATION
STARTERS
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If there’s one thing that can ruin a first date and ensure a woman’s first
impression of you is a bad one, it’s crappy conversation. You need ice breakers,
light-hearted queries, questions that provoke banter, laughter, and thought, as
well as questions that dig a bit deeper and go beyond the superficial. To save
you from endless awkward silences, we’ve compiled 50 first date conversation
starters that do all of these things. Plus, they’re backed by professionals who
know what they’re talking about.

Meet the experts: Sarah Jones is a relationship expert, and founder and CEO of
coaching website Introverted Alpha, and Sameera Sullivan is the CEO of Lasting
Connections, an elite matchmaking service. Read on. Your future dates depend
on it.

1. 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.

2. 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.”

3. 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.

4. 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.

5. 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.
6. 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.

7. 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.”
8. 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.

9. 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.

10. 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

11. 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.

12. WOULD YOU GO ON

A CROSS-COUNTRY
ROAD TRIP?
This may seem a bit odd and specific, but how she likes to travel is sometimes
even more telling than where she likes to travel. Does she only stay in five-star
resorts? Is she into sustainable locales? Is she a bargain traveler? Is she up for
camping and RVing? All these alternatives offer “insight into her lifestyle, taste,
and knowledge about other cultures.” Sullivan says.

13. IN A NEW CITY,

WHAT ATTRACTION DO
YOU HAVE TO VISIT
FIRST?
Some say you never truly know someone until you travel with them. Odds are
you won’t be traveling on a first date, but this question (paired with the above)
can offer a ton of clues about her persona. “This opens the door for conversation
relating to history, religious perspectives, art, and culture,” Sullivan says. If she’s
crazy about museums and monuments, you can infer she’s a history buff—or
better yet, ask her if she’s a history buff. Let one question lead to another.

14. WHAT ARE 5 THINGS

YOU WANT TO
ACCOMPLISH BEFORE
YOU DIE?
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.

15. 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.
16. WHAT ARE YOUR
FAVORITE SPORTS?
“If sports are big in your life, this will take you into a ton of subtopics,” Sullivan
says. Ask what sports she’s interested in, what teams she roots for, and if she
played sports in college. Depending on her answer, you can see whether you’re
up for some healthy competition or standing behind the same teams. And if she
doesn’t care, then you can decide whether it’s a slight turn off or a deal breaker.

17. 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.

18. 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.
19. 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.

20. WHO HAS BEEN THE

MOST INFLUENTIAL
PERSON IN YOUR LIFE?
“Instead of asking how close she is with her family, ask: ‘Who’s the most
influential person in your life?'” Sullivan says. “This will tell you more about her
family dynamics and close relationships she has with friends.”

21. 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.
22. 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.

23. WHAT’S YOUR

FAVORITE ANIMAL?
Light-hearted questions like this one can stir up memories from her childhood. It’ll
also let you know if she’s a pet lover. It may seem silly, but if she hates dogs and
your Husky is part of the family, or she’s got two cats and you’re allergic, things
might not work out.

24. 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.

25. 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.

26. 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.

27. 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.
28. HOW DO YOU LIKE
TO SPEND YOUR
NIGHTS?
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.

29. 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.

30. WHAT’S YOU ALL-

TIME FAVORITE
SONG/ARTIST/BAND/GE
NRE?
“Asking about her favorite song, band, or artist of course tells you about her taste
in music,” Sullivan says. But you can branch off and find out what her first
concert was, who she’s dying to go see, and if the cards work in your favor,
these bits of information can turn into a phenomenal future date or surprise.
31. WHAT ARE YOU
MOST AFRAID OF?
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.

32. 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.

33. WHO’S YOUR BEST

FRIEND?
This may or may not be the same person she spends the most time with, but
both people are obviously key to who she is. If her best friend is someone she
grew up with or someone she’s close with because of a particular incidence
(good or bad), ask her about it. This is someone she cherishes in life, so it’s a
sweet gesture to show a genuine interest in that person, too.
34. ARE THERE
MISCONCEPTIONS
ABOUT YOURSELF YOU
WISH PEOPLE
WOULDN’T MAKE?
This is a ballsy question, so use your discretion. In the right context, though, it
can let her clear the air or dispel any frustrating assumptions people make about
her. Let her take this question where she wants, and don’t be too pushy.

35. IF YOU WERE TO

PATENT AN IDEA OR
THING, WHAT WOULD IT
BE?
This question gives you major brownie points for being clever. You can see how
her brain works and how clever she is, too!

36. 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.

37. WHAT’S BEEN YOUR

BIGGEST REGRET IN
LIFE?
Like some of the other questions on this list, feel out the conversation and only
ask this one if the moment feels right as it could make her feel uncomfortable.
Try to slip it in to conversation if she mentions a career path she could have
gone down or a trip of a lifetime she never took. Just tread lightly.

38. WHAT WOULD YOU

BE DOING IF YOU
WEREN’T IN YOUR
CURRENT JOB?
This is a twist on the “dream career” question, but will result in an answer like
“lawyer” rather than “movie star.” What she went to school for may not be the
field she’s in now. Likewise, what she studied in school may not be her dream
career anymore. This is a fun way to pick her brain and get her talking about
what her interests and passions are.
39. WHAT DID YOU
WANT TO BE GROWING
UP?
You can use this question as a preface or follow up to No. 38. Both of you get
the floor to speak about your childhood. You’ll have endless stories… chock-full
of embarrassing confessions and lofty dreams.

40. WHAT WAS YOUR

YEARBOOK QUOTE?
High school is a time of awkward stages and thinking you’re funny when you’re
really not. Ask her what her yearbook quote was. If she didn’t have one, ask
what it would have been, or what she would make it now?

41. 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.
42. WHAT’S THE LAST
EVENT YOU BOUGHT A
TICKET FOR?
If she’s going to dish out $100+ on tickets for a Broadway show, sporting event,
or concert, it shows it’s important to her and something she thoroughly enjoys
doing. It’s a roundabout way of seeing what her interests are in detail without
straight out asking.

43. WHAT’S YOUR

FAVORITE CHILDHOOD
MEMORY?
You want positive vibes only on a date. By posing this question, you get her
thinking about some of the best times in her life. You’ll also get a peek into family
traditions and dynamics.

44. ARE YOU CLOSER

TO ONE OF YOUR
SIBLINGS?*
You’ll find out how close or far in age she is with her siblings, how many brothers
and sisters she has, and how they interact with one another. If you’re big on
family, this question is a must.
*Of course, this only applies if you’ve already asked about her family and she
does, in fact, have more than one sibling!

45. 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.

46. WHAT’S THE MOST

EMBARRASSING THING
THAT’S EVER
HAPPENED T
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.

47. 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.
48. 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.

49. WHERE CAN YOU

SEE YOURSELF LIVING?
This question is more revealing than you’d think. If she has plans to move to
Toronto next year, she might not be in a place in her life where a long-term
relationship is feasible. Likewise, if you’re deadset on living in a city, whereas
she’s dying to live on a farm, there are going to be conflicting desires that can
spell disaster for a relationship.

50. WHAT’S YOUR

FAVORITE WAY TO GET
ACTIVE?
If you’re on this website, fitness and health are obviosuly important to you.
Instead of asking her if she works out, see what her favorite physical activities
are instead.

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