There’s nothing quite as exciting as dating someone new. From the thrilling firsts—like romantic trips away and using cute nicknames—to the everyday moments like cuddling on the couch and goodnight texts, the feel-good vibes are typically out in full force during the initial stages of any situationship. But if you ever plan to get past the honeymoon stage, you need to take some time to get to know each other on a deeper, more intimate level. While sure, exploring each other sexually is great, exploring each other emotionally is equally important. And asking questions to get to know someone is a great way to build that bond and create what could become a lasting connection.

The key here is to ask questions that reveal the tiny little things that make your partner them. You don’t need to have another convo about the forecast or whatever you watched on TV last night. Instead, hit on topics that dig a lil deeper, promote stimulating discussions, and help you understand each other a bit better.

Quick disclaimer: You do have to enter into serious, personal territory to really connect, but not all the questions have to unpack past trauma and lead to tears. They should, however, all be engaging and require more than a “yes” or “no” response. The goal is simple: Get them talking.

If you’re feeling stumped, we’ve consulted with dating and relationship experts on the best questions to ask when you really want to get to know someone. Not only do these work for romantic relationships, but they’re great to talk about with your friends, parents, strangers on a plane—you name it! Whatever the situation, here are the top 100 Qs to ask so you’ll never have to talk about the weather again!

1. What’s one question you wish more people asked you?

This simple Q tells you what they enjoy talking about, what may be their passion, and as a bonus, “this gives the individual a very open-ended approach to share things that may be hard to prompt,” says licensed psychologist Carly Claney, PhD.

2. What makes you feel accomplished?

We all measure accomplishments differently, and you typically value the things that make you feel accomplished. So whether it’s receiving praise at work, protesting for a good cause, or reaching a fitness milestone, this is a good indication of what makes them feel fulfilled and successful.

3. Did you have a childhood best friend growing up?

Asking about someone’s early years can feel like a lot, so instead, ask about a (likely) positive source of comfort from their younger days. Childhood BFFs can majorly shape us as people, so this might cue you into why they went into their specific line of work or why they love watching movies on Saturday mornings. Besides, it’s always sweet to see someone get that far-off, nostalgic look in their eyes when talking about a friend.

4. What’s your strangest talent?

It’s usually easier (not to mention more fun) for people to talk about their talents when it’s a little less, “I’m really good at public speaking,” and a little more, “I can balance stuff on my head.” Not only will you likely get a show (I mean come on—you’re a good balancer? Show me now!), but throwing this Q into the mix after a few heavier questions will keep things balanced.

5. Do you have any spiritual beliefs?

Some people might connect over religion right off the bat, but others might have spiritual beliefs that aren’t as out in the open. Sure, this can give you insight into whether you’ll be expected at midnight mass should you end up together, but it can also shine some light onto the guiding force behind many of their actions and morals.

6. Do you believe in life after death?

This might be an obvious answer based on the above question’s answer, but plenty of people have beliefs outside of religion. This can be extremely insightful and personal, so make sure to actively listen to their answer and don’t try to talk them out of their beliefs. If you want a fun follow-up, ask them what their version of heaven would look like. It’s puppies, loved ones, and lots of pizza rolls behind those pearly gates for me!

7. What’s your go-to karaoke song?

Some people love public singing and others would rather sit on the sidelines, so sure, you’ll get that answer v quickly. But either way, try to phrase this as a “you haaaaaave to sing” kind of thing. What song do they know every word to, and why is that song such a big deal to them? If things are going well, you can absolutely request a performance then and there for a playful vibe change. Just be ready to mic up as well for a spontaneous rendition of “Toxic.”

8. What’s the last dream you remember?

…Or what’s the last dream they remember that they’re comfortable sharing? Dreams can get weird, y’all, but oftentimes they cue you into what your subconscious is trying to work through. Make a non-judgment rule so you can discuss your dreams freely without fighting over the fact that one of you had a sex dream about Jim Carrey’s Ace Ventura.

9. What’s the *best* dream you remember?

The definition of a “good dream” really varies depending on the person, their mood, and their values, so while this question seems a little silly, it’s actually pretty deep. Whether their favorite dream was when they got to spend time with their grandmother who had passed away years before or got to live in a house made of cheese, you’ll get some good intel.

10. Do you have a life motto?

If someone has a mantra, that’s one of the greatest indicators of how they *want* to live their life, so pay attention to what they say and see how it aligns with your own goals. Are they a “live fast, die young” or a “slow and steady wins the race” type? There’s a biiiiig difference in how those two people will likely want to spend their future.

11. What’s your favorite snack food?

This is one of the questions that separate the health nuts from the junk queens. Clashing over diet and food preferences can make picking a place to eat or stocking the fridge a major headache down the line (but don’t worry—it’s not a make-or-break. Relationships are all about compromise after all). On the flip side, however, you may learn about a yummy new treat or discover you both have a weakness for Cool Ranch Doritos.

12. Cats or dogs?

Cat and dog people can coexist, but for many of us, a future without a furry friend isn’t a future at all. That’s why learning where your S.O. stands on the matter is pretty major. P.S. This question can likely lead to stories of past pets, so get the tissues out and be prepared to feel your heart melt.

13. Did you have pets growing up?

If you didn’t get the details about their history with pets in the above question, ask away! Sure, you’ll get more insight about their stance on wet noses and litter boxes, but more importantly, asking someone about pets growing up is an easy way to segue into chatting about their childhood.

14. Are you an introvert or an extrovert?

Learning whether your partner feels energized around people or when solo chilling is major since neither of you wants to be depleted when making plans. Also! It’s important to remember being extroverted isn’t the same thing as being outgoing, so your partner might be chatty, but they might still think of themselves as introverted because they need plenty of alone time to recharge.

15. What’s the next big purchase you want to make?

Finances are one of the biggest things couples fight about, so having a similar viewpoint surrounding how to spend (and save) money is vital to most relationships. If your partner has been saving up for a new laptop to replace their 7-year-old model: Great! If they want to buy a new gadget because they’re already bored of the one they got a few weeks ago? Not necessarily as great.

16. What’s the best dish you can cook?

This is more telling than asking someone if they *can*, and it’ll give you insight as to how good of a chef they really are. Let’s face it: Mastering cereal is different from mastering Julia Child’s boeuf bourguignon. Regardless of their culinary prowess, cooking is an act of passion and a way to express love for many people, so if they ever offer to whip something up for you, there’s likely more meaning to the meal than just sustenance.

17. What’s your dream car?

First, this will let you know whether or not you’re dealing with someone who loves the Fast and Furious franchise *shudders*. But even more importantly, it shows you how they place value on themselves and the world around them. Do they want a flashy sports car for confidence? Are they aching to go electric for the environment? Or do they just want something that’ll get them from point A to point B?

18. Do you want to stay in your current work role for a while?

Asking someone about their work is sticky because hi, it’s work. So instead of something abstract like if they like their job, asking if they plan to stay in their role for a while is easier to answer. Plus, if you’re looking for a partner who’s at a consistent place in their life, this will give you insight as to whether a major life change is on the horizon, career-wise.

19. What’s your favorite conspiracy theory?

From the happenings at Area 51 to the moon landing, everyone’s got a conspiracy they can’t wait to talk about. Sure, this might give you an idea about whether or not you’ll be watching unexplained mystery documentaries for the rest of your life, but more importantly, it’s a purely fun question that keeps things from feeling too interview-y.

20. Describe yourself in three words.

The ~tell me about yourself~ question is basically a conversation ender, but by limiting your personal descriptions to just three words, you don’t have to feel like you’re giving an elevator pitch. And if they’re really struggling to come up with something, ask them to describe their “today self” in three words instead.

21. What’s the best way to wake up in the morning?

Whether they’re a 5 a.m.-er who runs or a 9 a.m.-er who snoozes 10 times, morning routines are sacred for many. Now’s the time to figure out if your ideal mornings align or clash. And if they don’t have a special way to start the day, maybe you can help them come up with one? *wiggles eyebrows suggestively*

22. Oh, no! There’s a spider in the house. What’s the move?

There’s a lot to be said about how someone interacts with small challenges and fears. Does the hero cape come on or does the fear take over? Also, if you find yourself in the company of someone who saves the spider and releases it outside (aww!), hang onto them tight since they clearly aren’t afraid of doing the right thing, even if it’s a tad uncomfy.

23. How do you feel about reality TV?

Reality TV can be kinda polarizing, and while some people love it (hi, it’s me), others aren’t as about it, so find out if your viewing preferences align. Also: This question can result in either a lively discussion about the merits of the genre or hours spent comparing your favorite Bachelor contestants, either of which is bound to be a fascinating convo.

24. What was the best trip you’ve ever been on?

There are a whole lotta ways you can vacation, so see if their idea of a chill break is the same as yours. Ideally, you’ll both find similar types of trips alluring, but even if not, pay attention to what it is they really liked about their best vacay ever. Was it the destination? The company? The food? This will reveal what they value in their time off.

25. Do you play board games?

Nope, not a super deep question, but definitely a favorite to ask. Board games are an epic—and screen-free!—way to connect, so finding someone who shares your affinity for ~Free Parking~ is pretty special. If they’re not a board gamer, maybe you can teach them a thing or two, and if they are into games, you can discuss the unlikely merits of having a sheep port in Settlers of Catan.

26. Where are you most likely to be at a party?

There’s nothing worst than going to a party and turning to find the person you arrived with is MIA. You don’t have to have the same social setting mentality, but knowing how each other functions and flourishes at parties is supes helpful. You’ll learn how they feel about social situations and for future reference, you’ll know that if you can’t find them, they’re likely playing flip cup or petting the host’s dog in the off-the-limits bedroom.

27. What’s your biggest pet peeve?

Pet peeves can honestly wear down even the most level-headed person, so you might as well learn about each other’s simple frustrations as early as possible. From the toilet paper hanging wrong to hearing someone bite the fork when they chew, discovering those peeves—and then trying to avoid them for each other—is a simple way to show you care.

28. If you could have dinner with one person (living or dead) who would it be?

This is such a fun question because it almost always leads to insightful conversations. Some people choose to dine with a deceased relative or historical figure, while others pick inspirational creators or famous celebrities. Be sure to ask them *why* they selected their chosen dinner guest to better understand what they admire in others.

29. What was the worst phase in your life?

Maybe it was the time they got bangs, or perhaps it was the three years when they moved five different times. We all have ups and downs, but learning about your partner’s (or potential partner’s) “worst phase” can help you prepare for future obstacles and understand how different situations might trigger or affect them.

30. What would you do if you won the lottery?

From paying off student loans to setting their parents up with a house or simply blowing it all on trips and (v expensive) treats, there’s a whole lot you could do with a giant sum of money. While you shouldn’t take their answer *too* seriously (this is hypothetical, after all), this will likely shine a lil light on their values and nature of giving.

31. If you were an animal, what animal would you be?

This is a fun one because the person might base their animal on aesthetics, size, personality—anything here goes. Yes, it’s a silly Q, but it actually shows what the person sees as their defining features, whether inwardly or outwardly.

32. What animal would you *want* to be?

You know what animal they would be, but now find out what they’d like to be. Dreaming of being super strong or fast like a cheetah might indicate they want to propel themselves to greatness, while choosing an animal that’s more mild-mannered like a bird might indicate they just want to coast and enjoy the view.

33. Would you prefer to go camping or chill at a resort?

There are two types of people: those who love to camp and those who don’t. While everyone should probably sleep in a tent at least once for like, life experience, beyond that it’s a total preference thing. And being with someone who wants to sleep outside every weekend when you’d prefer to be posted up at a bougie hotel pool is good to know so you can plan your future vacation days accordingly.

34. Did you have a favorite toy growing up?

Even the toughest of folks likely had a cuddly lil bear growing up, and exchanging stories of your favorite toy is a sweet way to relax the vibe. If they’re struggling to pick a favorite stuffed animal or doll, ask instead about the best gift they ever received as a kid.

35. What do most people overestimate or underestimate about you?

You know what they say about assumptions, right? This question shows how your (potential) partner would like to be perceived and how they feel the world’s view of themselves aligns with their own.

36. Have you ever lost someone close to you?

It’s a hard conversation to have, but losing a friend or loved one can really shape someone as a person. Practice active listening and be mindful if they’re not ready to go into detail. When they do open up about their loss, make an effort to remember the details and be cognizant of dates/reminders that could spur on memories or feelings of loss.

37. What’s a moment you’d love to be a fly on the wall for?

Here’s how to figure out what types of moments totally wow your date. Some people might lean toward historically significant events, whereas others might like to see something from their family’s lineage, or watch an especially important moment in their life back. Be sure to ask follow-up questions to really understand what draws them to that scene.

38. How did your family connect growing up?

Since childhood traditions can easily blend into adulthood, how their family bonded growing up could be a major way they like to form bonds now. For some people, that might mean playing Monopoly. For others, maybe it’s eating dinner together every night, or watching TV together in the evenings. If that connection style still feels good, you now have a secret weapon for creating close feelings with ’em.

39. What scrambles your brain every time you think about it?

If it’s anything other than black holes, they’re probably lying (I mean—come on! What is happening there?!). No, tbh, chatting about those things that just turn your mind into scrambled eggs is actually a lot of fun. You get to learn a little more about what things they ponder over and how their brain works, and you get to take turns attempting to unravel each other’s greatest mysteries.

40. Are you a better talker or listener?

Sure, the question itself is interesting, but it’s how they answer it that really shows the answer. Do they launch into an eloquent and thought-provoking response or do they turn it back on you and listen closely? It’s like an inception question.

41. What’s your “and then it got worse” story?

Whether it was a travel trip from hell or a group project that cost them a passing grade, everyone’s got a story where things just keep going wrong. As they share, pay attention to their body language—are they tense? Laughing? This could indicate how they’d handle future situations where things go awry.

42. What are you most determined to accomplish?

This question is like a double question, because sure, you’ll learn about their largest and most current goal, but you’ll also get an idea of where their priorities lie. If they’re striving for that big promotion, work is major right now, but if they want to run a marathon or buy a house, health and stability might be what they’re working toward.

43. What’s your favorite season and why?

Are you going to be hosting BBQs in the summer or Halloween parties in the fall? No, it’s not super deep, but this is a date, not a therapy session. Throw some fun ones in the mix to keep things balanced.

44. What do you hoard?

Maybe it’s memories, maybe it’s cat mugs. Their answer to this q can tell you what holds true value to them. Also! If they’re a legit hoarder, it’s probably a good idea to know that sooner rather than later so you can address it. Just saying.

45. What year was your favorite birthday?

Was it the year their friends threw them a huge surprise party, or the year they spent alone, drinking beer and reading a book? Sure, this can help you come up with ideas down the line, but more importantly, it gives you an idea of what makes them feel special.

46. What’s your favorite way to spend a day off?

If you’re the kind of person who wants to spend your weekends relaxing with some wine instead of waking up early to go hiking, it’s a good idea to see if your future partner’s on the same page.

47. What’s your favorite part of the workday?

Granted, plenty of people aren’t the biggest fans of clocking into their jobs, but are you with an optimist or a pessimist? Regardless of how much your job sucks, there’s probably something good about it—even if it’s just the iced coffee that makes you 15 minutes late every morning or the check that pays for your shoe obsession. This can clue you in to whether you not you’d be listening to work complaints every day for the rest of your life if you end up together.

48. Have you ever been to a family reunion?

Not only will this give you deets about their extended family (and if you’ll be expected to go to their grandma’s house every 4th of July), but it can also be how you learn if they have a secret castle in England or is the heir to the Toaster Strudel fortune.

49. Where would you be happiest to live?

First of all, it sucks to start getting serious about someone only for them to move across the country because they always wanted to live in Colorado. Potential LDRs aside, someone’s dream location will probably give you a good idea of what sort of environment makes them happiest.

50. Have you ever read a book that changed your life?

Especially if you’re a reader, this is a super powerful question. Books tend to be extremely personal, and knowing what genres they like and what stories moved them can give you a deep insight into who they are. Plus, you might just get some awesome book recs that you two can chat about on your next date.

51. What age do you feel like?

As someone who feels like a perpetual 12-year-old, this is always an interesting one to ask. Are they an old soul, or young at heart? This can also give you an idea of where they are in their life because if they feel older or younger than their age, it might give you an idea of what they’re looking for in a relationship.

52. When was the last time you felt excited? And what was it for or because of?

Licensed marriage and family therapist Billie Tyler suggests following up with questions like “What do you think excites you about that?” and “How do you know you are truly enjoying something?” to dive even deeper.

53. What’s the funniest thing your inner child wants?

Maybe it’s to eat dessert before dinner or twirl around outside while singing at the top of their lungs. Whatever it is, it’s the perfect excuse to do something unique on your date and learn a little more about their playful side.

54. If you ended up in jail, what would your friends and family think you did?

This answer could go one of two ways: It could be funny—like, I’d personally be arrested for robbing a CVS of all of their Reese’s peanut butter cups. But it could also be more serious and bring up events that may have happened in the past.

Just remember: “You want to get into the person’s values, personality, beliefs, and pivotal moments that made them who they are today,” says relationship expert Sophie Mona Pagès, founder of LVRSNFRNDS.

55. What’s your go-to French fry dip?

No, it’s not going to solely determine whether you have a future together, but a shared love of ranch could be the start of a beautiful relationship. Also, whether they’re a health nut or feel impassioned about waffle fries over curly fries, this is your chance to learn more about their food habits and drunchie preferences.

56. Have you ever become intensely invested in the fate of a TV show character?

This is more fun to ask than “what’s your favorite show” because it’s a little more nuanced and gives insight into the types of characters that capture your date’s attention. Follow up with questions about why they were interested in the character and how they felt about where their story went (if you’re cool with spoilers, that is).

57. If your life were a movie, what scene would you watch over and over again?

One time a date hit me with this question, and I’ve loved it ever since. It may take the person some time to come up with an answer on the spot, but it’s worth the wait.

58. Thoughts on scary movies?

Apparently, if both of you are into scary movies, this is highly compatible, says marriage and family therapist Kati Marquez Meyers. Oh, and “people who enjoy scary movies tend to enjoy other adrenaline-inducing activities and also tend to identify themselves as risk-takers.”

59. What movie always makes you sad? What movie makes you happy?

Are they a Titanic type of person or a Lincoln type? Might as well know now if you’re going to be faced with a lifetime of falling asleep in theaters or arguing over who gets the remote.

60. What embarrassing moment has stuck with you over the years?

We all have moments that make us want to crawl in a hole and die, but being with someone who can laugh at past missteps is an extremely attractive quality, and shows they might be good at letting things go. Just be prepared to dish your embarrassing moments if you bring this up in convo!

61. On a scale of 1-10, how well do you seize the day?

Adding a scale makes answering more abstract questions a little easier since chances are their response changes depending on the day, situation, and mood. Listen to their response and the “why” after it as well. Are they working hard to build a foundation for the future, or do they care more about experiencing the now and aren’t as focused on what’s down the line? This can cue you into their goals and how they might align with yours.

62. What would be your last meal?

This is more fun to ask than “what’s your favorite food,” and you’ll probably get a better idea of the specific dishes they like. Plus, if this is a love connection, you now have the perfect menu for their birthday or special occasion.

63. What do you like about yourself today?

Some days we feel more confident than others, but it’s always important to take time to remember why you’re awesome. This will also give you some idea of what they value in others, whether it’s that their hair looks good or they spent all morning meal prepping for the week.

64. What is an area of your life where you feel like something is missing?

Meyers adds: “This question inspires self-reflection and invites discussion into your partner’s deeper innate wants, desires, and areas where they might be feeling inadequate.”

65. Does social media make you feel better or worse about yourself?

Are you looking for a partner who will share their life with your followers or someone who’s a little more private? How do you feel about being with someone who spends a lot of time scrolling? Chatting about your opinions and expectations surrounding social media can help determine whether you’ll be compatible down the line. If one of you is always taking selfies and the other doesn’t know how to hashtag, you might find yourselves butting heads.

66. What’s the best decision you’ve made in your life?

We all have a story to tell, and this question specifically gives a glimpse of a person’s past and how they tackle challenges in their life.

67. What’s the best decision you’ve made today?

Do they love that they took a walk? Wore the green shirt? Ordered the pasta instead of a salad? This will give you a glimpse at what they value in the everyday. Pro tip: You might want to follow up that this isn’t a trick question so they don’t think they have to answer going on the date with you.

68. Would you consider yourself healed from the past?

This includes whether they’re healed from their past breakup, childhood trauma, a recent conflict at work, etc. “You don’t want to enter a relationship with someone who will project issues of the past onto you that are unrelated to you,” says counselor Sarah E. Williams. “Asking this question can help you determine if they are whole and fully ready to love.”

69. Which traits of your parents do you hope to never gain?

This will give you some insight into their relationship with their family, and it’s a more subtle way of asking about what they value as well. Do they hope to be more present? Better at providing? Do they think their parents are perfect (which could also cause problems down the line)? Pay close attention not only to what they say but how they say it.

70. Which traits of your parents do you hope to adopt?

On the flip side, you want to know whether or not they see the good in people, and what sort of traits they value in others. Do they idolize their parents’ cooking skills? Ability to fix anything? Work ethic? No matter what their relationship is like, there’s a good chance there’s something they admire about their folks.

71. What are your long-term goals?

This is the super subtle (but actually genius!) way of asking someone what type of relationship they’re looking for. Like, hi, are they envisioning a life full of kids and family vacays, or do they talk of traveling solo with no mention of a long-term romantic partner? While they don’t need to be like, “I WANT TO GET MARRIED NOW,” at least a general future plan that could involve an SO is nice to know before you get in too deep.

72. What are some of your biggest fears?

This can be as simple as spiders and snakes, or as deep as commitment, loneliness, and/or abandonment. “This question allows individuals to understand their partner’s vulnerabilities and sharing fears will strengthen the foundation of the relationship,” says psychiatrist Leela R. Magavi, MD. “It will also help gain insight into someone’s past and what helped to shape them.”

73. What are some of your biggest irrational fears?

Now that you got heavy, let’s get a little light. Irrational fears can actually be very telling about past experiences, or you just might have a chuckle over the fact that you’re both deathly afraid of peeing with the shower curtain closed.

74. What music really affects your mood?

Maybe they get amped up with show tunes or can’t stand classical music. While a shared taste of music isn’t exactly a deal-breaker or sealer, it will not only give an idea of their likes and dislikes, but it can shine a light on how different stimuli affect their moods.

75. Who do you look up to the most?

In whatever way you want to interpret it, there’s a big difference between looking up to your grandpa versus someone like LeBron James. Whoever they look up to, this question will help “conceptualize the partner’s core values and personality type,” says Dr. Magavi.

76. What’s your love language?

Truly, the MVP of all questions. “This helps individuals identify their partner’s mode of giving and receiving love, which may improve communication and strengthen the relationship,” says Dr. Magavi. So take the quiz yourself to find out which of the five love languages is your strongest: words of affirmation, physical touch, quality time, giving and receiving gifts, or acts of service.

77. Where do you see yourself in five years?

“This question is great because it gives you an idea of that person’s goals and life vision. You can determine if they’re compatible with yours,” says Jonathan Bennett, a relationship expert.

78. What do you love most in your life right now?

This question unpacks not only what the other person values, but also lets you glance into your potential compatibility, says Veronica Grant, a love and life coach. There’s no right or wrong answer, but depending on your personality (like you’re a go-getter and they’re happy just coasting through life), this question will take you straight to any potential personality clashes. You can either weed them out, or start a fun convo about what the two of your visions together would look like, says Grant.

79. Which TV or movie character do you identify with and why?

“I love this question because it breaks the ice and helps paint a picture without anyone getting caught up in their own ego. We are taught to identify ourselves by our jobs, hobbies, and our education (boring!), and this question totally lightens things up a lot,” explains Nancy Ruth Deen, a relationship coach.

80. What was your last wish, like on your birthday or the last time you threw a coin into a fountain?

Their answer will let you know what they think is unfulfilled in their life and what they hope for, says Diane Strachowski, PhD, a licensed psychologist and expert on attachment theory. Did they wish for love? Money? A promotion?

81. What happened in your last relationship that led you two to break up?

“If they blame the other person and don’t take responsibility for their own part of it, watch out,” warns Margaret Paul, a relationship expert. Nothing says red flag like someone with nothing but “crazy” exes. Smh.

82. What is your relationship like with your family?

Not everyone is super close with their family, but depending on how they view their relationship with them, this can tell you a lot. “Sometimes, what’s going on in the family can have a big effect on the relationship,” says Paul.

83. Who did you turn to as a child when you were scared, lonely, or hurt?

If they say “no one” and dealt with stressful situations alone, this is a good indicator that this is how they’ll handle current and future stressors now. On the other hand, if they went to their parents all the time for everything, they might need a lot of validation from a partner, explains Strachowski.

84. What are you most proud of and why?

This question lets you see what they value and how they spend their free time, explains Strachowski. Are they most proud of how their city soccer team went 10-0 last year, or do their eyes light up when they talk about the coffee table they built for their apartment?

85. How do you deal with finances? Do you spend too much or too little?

Sure, combining finances is a step for WAY down the line, but still, it’s worth asking as finances can be a huge issue in relationships, according to Paul. It can also be a good indicator of how they deal with life, in general. Are spontaneous weekend trips to Paris going to be a thing? Or are you guys gonna cook dinner at home more often than not?

86. What do you need during periods of stress? Do you call someone to vent? Do you spend time alone to think it through?

How they answer will let you know what they expect from close ones during rough times, whether it be closeness and a shoulder to cry on, or space, explains Strachowski. If you wind up dating and you find that they withdraw from you when they’re lonely, remind yourself of this so you don’t take it personally.

87. Who is your biggest influence and why?

This question can give you insight into a person’s core values, according to Bennett. If they name their single mother for raising them, they value responsibility and family. If they rattle off someone like Woody Allen, you can run.

88. What are your favorite addictions?

By addictions, we mean anything from chocolate, to working out, to Netflix. “Everyone has some addictions,” says Paul. The question is, are they going to be honest?

89. Are you a neat person or a messy person? Are you an on-time person or a late person?

Someone’s baseline definition of “messy” can be super insightful. Are they gonna be pissed if you spread all your makeup out on the counter for a night out, or will you be annoyed if the laundry piles up on a chair for a week? “It’s much easier if you are both neat or both messy, or both on time or late,” Paul adds.

90. Use five words to describe your mother/father, giving examples to support each.

Depending on how they answer, you can gain a lot of info on what they did or didn’t get from their parents and what they admire or look for in a person of the opposite or same sex, says Strachowski.

91. Do you believe in karma?

“This is a good question to get to know someone because it shows whether they believe there are consequences to their actions,” says Laurie Berzack, MSW, a relationship expert and dating coach. If a coworker screws them over at work, are they going to stay up for days stewing about how to get revenge, or are they more the type to forgive and forget?

92. What was the scariest moment of your life, and how did you handle it?


This one is interesting because it can open the door to either emotional history or just life stories in general. Was it when they got laid off from their dream job or was it when they got lost while hiking with friends? How they answer reveals their ability to overcome conflict and challenges, says Berzack.

93. Where is your happy place?

Another open-ended cutie that can segue into good follow-up questions, depending on how they answer. If it’s a physical place like the gym, or that one great hiking spot on their favorite trail, you can talk about those interests. If it’s a more abstract answer like “any time I finish a book that’s so good I immediately flip to the first page and start again,” that’s a good convo starter, too. “This question allows you to learn what the other person truly enjoys in life,” says Bennett. You can also use it to plan for future dates, gift ideas, etc.

94. What makes you cry and why?


“Knowing someone’s soft side is important to know what triggers them. If they don’t cry, they may not be sensitive,” says Strachowski. Again, if you’re sobbing on a movie date in the future and look over to see nothin’ but stoicism on their face, they’re not a heartless robot—they just have a higher cry threshold than you.

95. When was the last time you got really angry, and why?

This can be an unobtrusive way to find out the extent to which your date is trying to control the world around him or her, says Berzack. Plus, it opens the door for some lighthearted hate-bonding, whether it be over little or big things. Was the last time they got fired up because someone cut them off in traffic? Or, when they saw a bunch of people during rush hour refuse to give up their seat to an elderly person?

96. What is your best quality?

“It’s always interesting to see what a person thinks is their best quality. By asking this question, you get insight into how the person views themselves and what they think is an important aspect of who they are,” explains sex therapist Christopher Ryan Jones.

97. Which song or artist are you too embarrassed to say you absolutely love right now?

Not only does this give you a chance to potentially geek out over which Taylor Swift album is best (the only correct answer is “Folklore,” obviously), but it also shows playfulness and vulnerability, especially if you’ve just met, says Deen.

98. Are you friends with any of your exes?

This question lets you know two important things in one, explains Jones. It gives you insight into their past relationships and how they ended (does everything seem to go up in a huge wreck or do things end amicably?), and if they are friends, you’ll know now and won’t be surprised if/when they get a text from an ex they’re still close with.

99. Ask them to complete this sentence: “I most enjoy having someone to do ______ with.”


Sometimes, a person’s intentions can be clearly discussed by simply asking them. Strachowski recommends listening closely to see if what they’re seeking aligns with what you can give someone right now. Are they looking for a romantic partner, a best friend, or just a casual movie buddy?

100. If money wasn’t a factor, what would you be doing with your life right now?

This is a fun one that can tell you a lot about a person and their passions without them feeling too self-conscious about it, explains Deen. Do they want to be directing movies? Working with animals? Traveling the world? Depending on their answer, you’ve also got great banter to go off of afterward.

Carina Hsieh
Sex & Relationships Editor
Carina Hsieh lives in NYC with her French Bulldog Bao Bao — follow her on Instagram and Twitter • Candace Bushnell once called her the Samantha Jones of Tinder • She enjoys hanging out in the candle aisle of TJ Maxx and getting lost in Amazon spirals. 

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