questions to ask a girlHere’s something we can both agree on:

Women tend to confuse men. Right?

It seems like they’re wired differently, and there’s an impossible gap between what she thinks, and what you think.

…And if that sounds familiar (and you don’t understand your confusing girlfriend/wife), you’re not alone. A lot of guys want to understand their girl even a little better, for two reasons:

  1. To know what makes her upset… and what he can do to make her happy (and pro tip… what makes her happy is to feel valued, respected and loved… but we’ll get more into that later).
  2. To know if there’s a real compatibility between them (because sometimes the confusion around her makes him think they’re not right for each other).

So… yes, you want to understand your girl better…but how? If we’re wired so differently, how can you hope to know what’s really in her head?

Simple: flat-out ask the right questions. Ones that fulfill #1, and answer #2.

…And to help you with that, I put together a list of 101 powerful, insightful, deep and generally good questions to ask a girl or girlfriend.

Each of these questions is designed to help you make her happy, fulfill her needs, and help you determine your compatibility.

10 Best Questions To Ask A Girl You Like – Powerful Conversation Starters to Get Her to Open Up

Watch this video on YouTube.

101 Good Questions to Ask a Girl or Your Girlfriend

Not all questions are created with the same goal in mind… so, I broke the questions down into four broad sections:

Now… remember:

The goal of each of these questions is to start a conversation. This isn’t “20 questions to ask a girl”… so on’t just ask a question, and immediately fire off a new question when she answers… ask a question, wait for her to respond, and then ask follow up questions that start a conversation. Make sense?

Questions to Ask to a Girl to Get to Know Her

The Goal: These get to know you questions help you to understand her history and traits, so you’ll know if you have long-term compatibility. If so, you’ll know her honest feelings and can value her even more.

Bonus Goal: To get girl-approved date ideas.

101. If you had a one-way time-travel ticket, when would you go to?

So… she has a ticket to go back in time, and she’s never coming back to the present. Which year would she go to?

Ask follow-up questions, like who she would want to see, would she get a job, would she try to change history, etc. Use this fun, lighthearted question to ask a girl to start an interesting conversation.

100. What was your dream job growing up?

Did she pretend to be a ballerina, a vet, a dolphin trainer, or a fashion designer when she was little?

…And no matter what she says, you’ll almost always get a fun and interesting answer… and by asking why, you’ll usually get to know a little insight into her childhood self.

PS: Don’t forget to tell her all about your dreams to be a fireman, a dinosaur wrangler, or an astronaut.

99. Would you rather live in the city or the woods? Why?

This was a question we featured in our post, 75 Good Questions to Ask to Get to Know Someone. It’s a good question to ask a girl to get to know her because it forces her to choose between two polar opposites:

Would she rather live in the crowded, constant action of the city? Or the calm, peaceful tranquility of the woods?

98. What’s your favorite holiday?

Does she love to dress up for Halloween? Does she want to snuggle up with you at Christmas? Or does she want nothing more than flowers and chocolate for Valentine’s Day?

…And guys, not only does this start a fun conversation, but it reminds you to do something special for her during that holiday!

97. How would you describe your personal style?

Girls often spend a lot of time and money on their signature look, and asking this gives her a chance to talk about it.

Now… I get it:

This is not the most fun conversation for guys. But it’s one that women love, plus it gives you some powerful information (think about it: if you know what she likes best about her look, and compliment that specifically, it will be hugely more impactful compliment.)

96. Where’s your favorite restaurant/dessert spot?

This is a good question to ask a girl because it broadly tells you what type of dates she likes:

Is her favorite place high-end and classy? She probably prefers upscale, expensive dates. Is it vegan or all-organic? She likes to know what goes into her food. Is it a pizza joint/beer garden? She’s low-key and easy to please. Maybe the place she names just has special memories to her.

PS: After you’ve found out her favorite spot, wait a few days, then take her there or somewhere similar for a great date night!

95. What activity/hobby makes you the happiest?

Does she love horseback riding? Dancing? Spending time with friends? Binge watching TV?

NO matter what it is, this question shows what she does in her free time and will subtly give you another perfect girl-approved date idea!

94. What’s the best gift you’ve ever received?

Give her a minute to think about this one… she’ll probably have to dig into her memories to come up with the answer.

But after she does, the best part of this question is she’ll usually explain why it was great without you having to ask. Now… when she’s explaining the why, pay attention. This will give you invaluable insight into what she values most in gifts (and will make her birthday and Christmas easy).

PS: If there’s a holiday coming up, and you still need gift ideas, check out the Mantelligence selection of thoughtful gifts here.

93. Did you have a pet(s) growing up?

This is a good question to ask a girl, but, really, is a good question to ask anyone.

Why? People love their pets and love to talk about them. Ask her pet’s name, what breed it was, and how old she was when she had him/her. Plus, this usually even leads to some fun childhood stories.

…And if she didn’t have pets, ask her why not. Does she want a pet now? This helps answer an important compatibility question if you were to live together: is she a cat person, a dog person, or neither?

92. So… how many pairs of shoes do you have?

This question is guaranteed to make her laugh… regardless of whether she owns one pair of Toms or 30 pairs of high heels.

After she answers, chances are she’ll explain why (usually in an attempt to rationalize the number). This almost always turns into a surprisingly funny and unexpectedly insightful conversation (because through her answer and explanation, you can usually get an idea of how high maintenance she is).

91. What’s your favorite comedy movie?

It seems like nothing more than a casual question, or a conversation starter… but her answer is actually really important. Here’s why:

Laughing together is a huge way couples connect, and you should be able to laugh at the same, or similar, things. Think about it: constantly telling jokes that she doesn’t think are funny, will get old quickly.

90. If you could take a two-week vacation… anywhere in the world, where would it be?

While it’s fun to daydream about vacations, this is one of the best questions to ask a girl because it gives you insight into how she views her lifestyle.

A vacation is an escape from the everyday. Is her ‘escape’ just rest and sleep on a beach? She feels overworked. Is her ‘escape’ drinking and partying in Vegas? She feels bored. Is it going on a family camping trip in the mountains? She feels lonely, and wants to connect with people she loves.

If you can understand what she wants to escape from, you know what pressures her… and get a good clue about how to delight her!

questions to ask a girl - vacation

89. What are your three biggest pet peeves?

This is a subtly good question to ask a girl because you basically just asked her “How can I not annoy you?”, so take advantage of this opportunity and listen.

…And make sure you tell your biggest pet peeves too… you want to stay together, so give her the chance to not annoy you, too!

88. Do you have a junk drawer? What would I find in it?

This is another question guaranteed to make her laugh, because it’s likely that she has no idea what’s in there. So have her guess a few items that are lurking in her junk drawer.

Bonus: you guess a few items that are in there (the crazier the better… her laughter is your goal!), then open up the drawer and see how right you were.

87. What’s the craziest, most spontaneous thing you’ve ever done?

This is a good question to ask a girl because it shows you her fun side! Have her describe her spontaneous moment, then ask her what made her do it, and if she would do it again.

Know what kind of adventures she’s open to, and if you both enjoy the same type of adventures.

86. Do you have any allergies?

This importance of this question should be obvious… you should know if you should not make her a shellfish dinner, or not bring her to your house if you have a cat.

…But the best part is that asking directly lets her know you care about her needs, which makes her feel special and valued.

85. What’s your night/morning routine?

Ok, this one’s a little sneaky… secretly, you’re asking how high maintenance are you? It’s good to know how much time she takes to get ready, and what time she expects your evenings together to wrap up.

Basically, you can be prepared to stick to her schedule if you ask her flat-out what her routines are.

84. Would you get a new tattoo? Of what? Where?

What’s important enough to her to mark on her body forever? Maybe she just values beautiful artwork and wants to turn her body into a work of art. Whatever her reasons are, listen to what’s important to her. Are the same things important to you (are they compatible with your views)?

If she already has tattoos, let her tell you all about them, and don’t forget to compliment each one.

83. Do you think of yourself as an extrovert or an introvert?

Extroverts and introverts can get along just fine, so don’t worry if you’re opposites.

Focus instead on her impression of herself… if you can understand how she views herself, you’ll understand her confidences and insecurities, and be able to support her through both.

82. When was the first time you broke the law?

This one will make you both laugh. Find out all about her rebellious (or not so rebellious) youth.

Make sure you trade stories!

81. When was the last time you broke the law?

Was it speeding on the highway? Buying alcohol for minors? Hopefully it wasn’t anything too troublesome!

Now… after you trade stories, ask what she would never, ever do. Again, it’s good to know her limits (especially when it comes to breaking any laws), so after you learn them, don’t push her.

80. Would you skydive? Bungee jump? Or do a similarly crazy thing?

This is an interesting question to ask a girl because her response is more important than it seems… because you have to know her limits, and what she’s comfortable with. If she’s not adventurous in the same ways you are, you might have to be ok with one of you having adventures without the other.

So learn her limits, then respect them. Don’t push her to do anything she doesn’t want to.

questions to ask a girl - extreme

79. Do you have any scars?

Women love to talk about youth and mishaps, because it shows her you really care about her history. Ask her all about the incident… how old was she, did she get to ride in an ambulance, did she get lots of gifts (or scolding) from her family, etc.

But be aware… a physical scar might be an insecurity for her. If she seems shy to talk about her scars or show them to you, don’t pressure her, but reassure her that she’s gorgeous no matter what.

…And if she has no scars, tell her how impressed you are!

78. How would you spend a billion dollars?

She’d never need to work again with a billion dollars… so what would she do? Travel? Buy a mansion and settle down? Start a charity organization?

Of course… it’s very unlikely that she’ll inherit or win that much money, but you get insight into what she wants to spend money on. Is it the same things you would spend money on… and more importantly, do you value the same things?

77. What was the most money you’ve ever spent on something fun?

It’s likely that blowing that money was a memorable, exciting experience for her, so listen to her share it.

Also, think about what you would spend your ‘fun’ money on. Would you two disagree about how to spend extra cash in the future?

76. Who is your best friend?

This is one of the more subtly deep questions to ask a girl because it hints at your long-term compatibility. Do you know her best friend yet? Do you like them? Is it a guy, and are you ok with that? You and her friend are both important to her, and you’ll probably have to hang out with her best friend at times… are you going to be ok with that?


Also remember that she listens to her friend. Be aware if her friend pressures her to get married quickly, or pressures her to be single, or tells her that you aren’t the right guy. If you and her best friend disagree a lot, there may be trouble in your relationship down the road.

75. Who did you vote for in the last election?

This conversation will let you know two things:

  1. Does she care about politics like you do?
  2. And are your political views compatible?

Now, discussions about politics can get heated, so don’t ask this on a first date (or maybe not even on the first five dates). But no matter what she says, listen carefully and be respectful of her opinions (even if you disagree). Couples can make relationships work if they have different political views, as long as they maintain respect for each other.

74. How many hours a week do you work?

This is surprisingly one of the best questions to ask a girl because it’s a huge compatibility indicator.

Is your workaholism going to bother her, or is she going to get mad that you’re ‘lazy’?

Look… differing expectations about work schedules and work ethics almost always cause fights. So make sure you each understand the value you place on your jobs vs. your free time, so you know what to expect from your partner.

73. Are you close with your parents/siblings?

Her family might be your in-laws, so their opinions matter.

Find out how much she values family connections… because it indicates how much she’ll value your family (and want you to spend time with them).

…And if you know the expectations of how much time is going to be ‘family time’, you can avoid confusion and conflict.

72. What does your perfect day look like?

Here’s an easy way to know what’s important to her… and get some hints about how you can really make her day.

Let her describe it in detail (bonus points if her perfect day includes you!), and remember the highlights. Then surprise her with those things/activities later.

71. Are you religious?

Guys: this is not a first date question! Religious differences can be a big deal to couples, so it’s important to understand not just what her religion is, but also how strongly she cares about it.

If she’s very religious, she’ll likely expect you to care about religion as much as she does.

70. How does your family celebrate holidays?

This seems like a lighthearted question to ask girls (and it will be fun for her to tell you about her traditions)but there’s a deeper question here:

Will you be able to honor both your family’s traditions? How to spend the holidays can be a huge issue for couples who haven’t discussed their expectations. You both should listen to each other’s values and compromise, ideally before the holidays come around and it turns into a fight.

questions to ask a girl - holidays

69. What’s your greatest fear?

There are two types of fears:

  1. External fears are physical, like spiders, big dogs, or ghosts
  2. Internal fears are emotional, like rejection, verbal abuse, or abandonment

Now, when she shares these fears, she’s deeply trusting you to not abuse this information. Don’t use her external fears to scare her (it won’t be funny to her), and don’t forget about her internal fears (watch yourself around them, and don’t hurt her in the ways she describes).

She’ll trust you even more deeply if you respect her fears, and protect her from them.

68. If you could go back in your past and change one circumstance/decision, what would it be?

This is one of the more interesting questions to ask a girl because it’s a gentler way to ask “What’s your biggest regret?”

And guys, listen and sympathize about her regrets… they can be hard to talk about. Reassure her not to be insecure about her mistakes, because she’s a stronger, better person for coming through them… and earn yourself huge bonus points by being supportive!

67. If you could have one superpower, what would it be and how would you use it?

Another question from our post 75 Good Questions to Ask to Get to Know Someone.

Does she want to fly? To be able to teleport? To be able to shoot lasers from her eyes? This is one of the most fun questions to ask a girl to get to know her. The answer is almost always interesting and always sparks a fun conversation.

66. What’s the biggest lie you’ve ever told?

This one can be hard to answer, so be patient and let her really consider it.

And here’s a pro tip:

Make sure you know who she lied to… if it was a boyfriend, put up a red flag in your head. Lying to an ex-boyfriend could mean that she’s willing to lie to you too, especially if she never came clean to her ex.

Interesting and Generally Good Questions to Ask a Girl

The Goal: Understand who a girl is on her own… what her strengths and passions are, and make her feel respected for them. Make sure you’re both on the same page with where your ambitions lie.

65. What skill do you have that you’re most proud of?

All women want to know that you value their successes. She’s worked really hard on being the awesome person she is, and it lifts her up when you listen to her success stories.

Now that you know what she’s proud of, encourage her to spend time doing it. And make her happy by letting her know that you’re proud of her, too!

64. If you had time and money to pursue a new skill, what would it be?

What is she dying to know how to do? Play the piano? Learn computer programming? Cook like a master chef? Whatever it is, listen to her description.

Plus, now you know to encourage her if she gets the opportunity to pursue that skill.

63. How do you define success?

If you understand what her long-term goals are, you’ll know what actions she values today.

…Like if she wants to start a new business venture, she’ll value saving money. If she wants to be a mom soon, she’ll value putting effort into her relationship and moving it along. If she wants to see new places, she’ll value taking a job that allows her to travel.

But whatever her idea of success is, you should be able to support her in it, and encourage her to do things today that get her closer to her goal.

62. How do you answer the ‘biggest strengths/weaknesses’ question in interviews?

Find out how she answers the age-old interview question. What does she think are her good traits and her not-so-good ones? And remember, you’ll have different views on her strengths and weaknesses… and that’s great!

That way, you can tell her a strength you admire that she didn’t name. Let her know you acknowledge when she’s great at something, and she’ll feel supported.

61. What causes do you support?

Know the charity she has a soft spot for… because she’ll want to spend time and money supporting it. Can you understand her connection to it, and value it as well?

If she doesn’t support any causes yet, find something to support together! Volunteering has a positive impact on individuals’ happiness, so share it.

60. What gets you out of bed in the morning?

What are her passions? Let her share every detail, and ask a lot of follow-up questions about her dreams.

You should get excited as she gets worked up about her passions… you’re there to encourage and support each other, after all. Share your passions too, and know how to help each other achieve a lot.

questions to ask a girl - out of bed

59. How different is 5-years-ago you?

While this is an intimidating to ask, it’s one of the best questions to ask a girl.

We both know that the older people get, the more they change. Outside circumstances evolve them into new people with different desires and ambitions.

So ask her how she’s evolved. She may be proud of the ways she’s changed, and she may be regretful, and both of those are good for you know… so you know how to encourage her to be her best! She needs a supportive teammate who wants the best for her… be that man.

58. What’s the first thing you do after you’ve accomplished something big?

Everyone has a way to reward themselves for achieving a goal. Some girls take a hot bath, some girls enjoy time at the gym, and some girls indulge in a bottle of wine.

Know what she does for just herself, and you can surprise her with it some time.

57. Have you ever owned a house?

Houses are a huge responsibility. If she’s been a homeowner, it shows that she’s mature and capable… and that signals a good relationship ahead for you.

If she hasn’t (or doesn’t currently) own a home, talk about the house you’d both like to have… because sharing ideas about your future will give you a powerful goal to work towards together.

56. Where do you see yourself in 5 years?

Where she sees herself should line up with where you see yourself if this is going to work long-term. Right?

So after you’ve listened to her goals, make sure your visions of the future are on the same path!

55. What do you do for you?

If you like this girl, you want her to be around for a while… and that’s what makes this one of the more interesting questions to ask a girl. It indirectly asks her, “What do you do to take care of yourself?”

The conversation is usually all over the place (she’ll talk about her hobbies, what she does to unwind, what she does to take care of herself, etc.)but the common theme is what she does to stay happy and healthy.

54. How do you think you react to failures?

Her answer will tell you two things:

  1. What she views as her failures
  2. How often she views herself as a failure

Both of these are big indicators of insecurities you’ll have to look out for, and be sensitive to. Reassure her that everyone fails from time to time, but she’s still great!

53. Who’s your role model?

It might not seem like it, but this is a compatibility question.

Do you respect her role model? Why or why not? She wants to take after this person… if she succeeds and becomes like her role model, it should be someone you admire as well.

52. What’s your favorite thing to blow money on?

This is one of the most fun questions to ask a girl… when she has extra, unexpected cash, what’s her dream splurge item? Maybe she wants a mini-vacation, or a shopping spree, or to put a down payment on a new car.

…So ask her this, and you’ll get a good idea of how to help her celebrate her future successes.

51. How much do you value your education?

Know the level of education she’s achieved, and be aware that she’s proud of that achievement.

Now… if you’re seriously dating, discuss what kind of education you want for your family. Will you encourage your kids to go to college? Will you only enroll them in private school? Is homeschooling an option? It may be the distant future, but knowing that you and her are on the same page will make you feel even more ready to tackle the future together.

50. If I gave you $1000 right now, what would you do with it?

This is different than the above question: if you gave her unexpected money, would she decide to blow it on something fun, or use it for something responsible (paying off debt, or starting a savings account)?

It really doesn’t matter what the answer is… the real questions is that if your incomes were shared, would you agree with her choice? Remember that your ideas about money have to be some what compatible if you want to stay together.

questions to ask a girl - $1000

49. What are you saving money for?

This is one of the more subtly powerful questions to ask a girl.

If she’s not saving, ask her why she’s not. Can she not afford it? If that’s the case, you’ll need to adjust expectations of the lifestyle you’ll have with her. Does she just not want to save? That likely won’t change on its own, so be concerned that saving money isn’t important to her.

If she is saving, knowing what for will help you understand what’s important to her, and if the same things are important to you.

Questions to Ask to Your Girlfriend

The Goal: These questions to ask your girlfriend are designed make her feel loved and to spark meaningful conversations.

But note that some are reserved for more serious couples.

48. Do you ever see yourself taking time off (for kids, for travel, for soul-searching)?

Couples should view their future together the same way. Both your views could change, of course…

…but if you’re thinking you’ll both work until you retire, and she’s thinking she’ll take time off at some point, you should talk about it now, so you know how to best support each other’s goals.

47. Which TV show should we binge watch together?

What’s that TV show she’s been dying to binge watch… Breaking Bad? The Walking Dead? The Wire?

It’s a really good question to ask your girlfriend because it gives you a great date activity that costs nothing, and (once you get caught up in the series) creates a fun, weekly event to look forward to.

46. What can I do to help you (with work, with your goals, in general)?

Guys, this might just be the biggest turn-on ever for women.

Ask her what she needs (help with a work project, the dishes to be washed, a few things picked up from the drug store)… and then do it for her. Sometimes your girlfriend is overwhelmed and frustrated, but doesn’t know how to express it… and if you show her that you’re the capable man who can help her handle her to-do list, she will reward you with equal love and respect.

…And make a habit of helping her, and you’ll be rewarded in the same way for life.

45. Do you think I should be a [insert your job title]? If not, what job do you think I should be doing?

Find out her general impression of you and your strengths.

Plus… she’ll love the opportunity to brag on you a little bit. Listing your strengths out loud will make her value you even more!

44. How do you feel about PDA? Do you think we ever do it too much?

Couples see PDA differently, and it’s good to know in advance how you both feel about it, so nobody feels brushed aside in public.

Make sure you ask this at a good time (for example, don’t ask while she’s already hugging you in a group of people)… otherwise she’ll think you’re rejecting her attention and feel hurt.

43. Which of my friends is your favorite?

Find out why she likes that personand you’ll know what traits she values in friends in general.

Now… if she says ‘none’, you should probably run. Your friends are your friends for a reason (even if she doesn’t understand why), and she should be respectful of your connection with them.

42. Do you see yourself ‘settling down’ some place? Where?

See if your future plans are on the same track. If you’re getting serious, you should know your partner’s long-term plans… and even be able to see yourself there with them.

So see if she has any ideas about where (or if) to settle that excite you. Talk about the future with confidence, and she’ll definitely know you love her, and want to stay with her in the long run.

41. Have you ever done a long-distance relationship?

A time may come when you have to do long-distance… so express now how you both feel about it. Do you both think a long-distance relationship can work long-term?

Be aware of her opinions, and have ideas about how you’d handle it. Again, planning for the future lets your girlfriend know you love her enough to work through potential problems with her.

40. What’s your ideal date?

This is a good question to ask your girlfriend because it’s hints at how she defines romance.

…And it doesn’t matter if it’s TV shows on the couch, a sunset drive, or a fancy dinner, as long as it’s with you! Understand her definition of romance, and you’ll have a better idea of how to make her feel loved.

questions to ask a girl - ideal date

39. Who was your first crush?

This is an infrequently asked, but really good question to ask your girlfriend.

Look… we’re all a product of our pasts, right? This question opens the door to talk about the pasts relationship(s) that made you who you are today.

38. Is anything a relationship ‘deal-breaker’ for you?

If she names a deal-breaker that you have, it’s best to know now, so you understand if you’re compatible long-term (for example, if smoking is her deal breaker and you smoke).

…But this question has another purpose: it also demonstrates that her opinions matter to you, which shows her she’s loved.

37. What fun thing do you want to do together that we haven’t done yet?

Doing new things together gives you both a rush of endorphins, and gives you a great memory to share…

…and doing something she wants to do makes her feel appreciated and loved, and you’ll hugely benefit from a happy girlfriend.

36. Where do you want to go tonight?

It’s a big turn-on for a lot of girls to be asked out directly. Just tell her “I’m taking you out, wherever you want to go,” and then don’t reject her suggestion (even if it’s not exactly what you want to do).

She knows you have to compromise on dates most of the time, but being treated like a queen every once in a while will make her feel amazing… and want to treat you the same way.

35. How are you feeling?

Ask her this when she’s obviously not feeling great, and show her you want to help.

Now… try not to ask “are you ok”… because she could easily answer a simple yes or no to that, instead of having a conversation about it.

Sit down, look in her eyes, and ask how she’s feeling. She’ll be incredibly grateful that you acknowledge her feelings… even if it’s something small that’s bothering her.

34. What’s your favorite thing we do together?

If you ask this, you’ll have a good idea of how to make her really happy.

Take her to do her favorite thing when she’s lonely, sad, or for no reason at all, and she’ll feel treasured and special.

33. What’s your favorite candy, alcohol, store, etc.?

You can always surprise her with her favorite candy when she’s sick, her favorite alcohol when she’s celebrating, and items from her favorite store for her birthday.

If you ask directly what she likes to be bought, you show her you want to make her as happy as you can… and she’ll love having a man that cares that much.

32. Is there anything you want to ask me?

I get it… this won’t always lead to the most fun conversation, but this is actually one of the most powerful questions to ask your girlfriend. Why?

Let’s say something’s bothering her that she hasn’t yet brought up… this question gives her the opportunity to talk about it. Again, while it’s not the most fun conversation, it allows you to quickly work through things, so they don’t build up (and eventually explode… which I know you don’t want).

31. When you’re excited/proud of yourself, how can I help you celebrate?

This one is pretty obvious… you want to help your girlfriend celebrate her accomplishments!

So find out directly from her how she likes to celebrate, and then take part in the celebration with her.

30. When you’re stressed, what do you do to relax?

Everyone has different routines and activities that help them unwind.

Know her routine, and if there’s anything you can help with. She’ll feel loved and cared for when you acknowledge her stress and try to fix it.

questions to ask a girl - relax

29. What’s the biggest turn-off for you (physical or otherwise)?

After you’ve found out what turns your girlfriend off, make a special effort to avoid those things…

…because listening to her desires lets her know you’ll always care about what she needs, and you’re the best man to take care of her.

Serious and Deep Questions to Ask to Your Girlfriend

The Goal: Find out how she likes to be taken care of, and let her know (through asking these questions, and then showing her you listened) that she is safe with you. If she feels safe, she’ll trust you and we all know: trust makes for a solid long-term relationship. But be aware: these are serious questions to ask a girlfriend.

28. Why did you and your last boyfriend break up?

Only serious couples should ask this… because in new relationships, asking this question can seem like you don’t trust your girlfriend.


She and her ex broke up for a reason, and it can be helpful to know why her last relationship failed, so you can avoid the same problems and stay happy together.

27. Do you think exes can be friends? Are you friends with yours?

Some people maintain friendly relationships with their former partners, and some people still shudder when they think about their ex. Is she friends with any of her exes… and are you ok with that?

Now tell her if you’re friends with any ex-girlfriends. It can hurt to find out that a good friend of your partner used to be a lover, so bring it up now before there are any hurt feelings.

26. What do you like most about me?

Your girlfriend chose to be with you for a lot of reasons, and she loves to brag on you. Give her the opportunity, and ask what she likes best.

Don’t forget to say what you like most about her!

25. If I was offered a job in another country/far away state, would you move with me?

These random opportunities come up sometimes, and it’s good to know how strongly you both feel about staying physically close together.

So would she move? Does she think a long-distance relationship could work? For how long?

24. Do you want kids?

Know how much and how soon she wants a family. A person who loves kids, connects with them easily, or talks about them often might be ready to start a family soon.

Now… is her view of children compatible with yours, and are your timelines similar? You don’t have to come to an exact agreement about a family, but be aware of what she wants, and know if it’s going to make you happy in the long run.

23. Do you believe in soul mates?

Girls can have very different opinions here. Some girls believe in ‘the one’, a pre-determined match, and some girls believe that no one is ‘perfect’ for their partner, but that people just make relationships work.

Now, you can be compatible if you believe differently about soul mates, but asking her opinion will let her know her thoughts are valued. And be prepared to answer the question back… she’ll definitely ask.

22. When do you know you’re really in love?

This is a really good question to ask your girlfriend because it’s an invitation to describe feelings of love (which will definitely make your girlfriend happy).

Tell her what, truly, feels like love to you, and listen to her describe the feeling. If you listen, she’ll give you hints about when she expects “The L Word” to be said, too!

21. What roles do you think are important for men/women to play?

Look… big arguments can come up when couples have different expectations of who does what at home (and warning: you both likely get your opinions from your parents).

If you’re thinking about living together, discuss now who will take care of what in the house… including taking care of any kids down the road.

20. What’s your parent’s relationship like?

This is one of the more powerful and insightful questions to ask your girlfriend because it will tell you a lot about her.

Some girls want marriages just like their parents’, and some girls want the exact opposite of their parents’ relationship. But if you know what type of relationship she grew up with, you’ll understand what she expects in her own marriage.

PS: There are a lot of follow-up questions you should ask when talking about parents:

Are they still married? How do they relate to each other? Does she admire their relationship? Why? Tell her about your parents’ relationship as well.

questions to ask a girl - parent's

19. What would you do if your best friend disapproved of me?

Sometimes, even though you treat your girlfriend like a queen, her best friend doesn’t see it. She may even whisper in your girlfriend’s ear that you aren’t right for her.

…And it’s important to know, especially when your relationship is serious, what will shake it (like her friend’s opinion). So talk honestly about why your friends’ opinions matter to you. Get an understanding about how sure you are about each other, and if anyone’s opinion could change your mind about your partner.

18. Is marriage important to you?

This is definitely reserved for more serious couples.

Find out if marriage is on her radar, and how soon she wants to get married.

Be aware: her clock might tick faster than yours, so if she’s more eager to get married then you are, try to listen and understand why. Openly talking about marriage will let her know you love her and respect her viewpoints.

17. What’s the sexiest thing I do?

She loves to know that her opinion matters to you.

…So even if she names something small, do more of it, and show her that you’ve listened and you care!

16. What would you do if one of our jobs started impacting our relationship?

Now, she probably won’t have an answer for this question ready the moment you ask (so give her a minute), but it’s good to talk about.

What would you do if your job or hers pulled you apart more often? How would you both expect to handle the separation? If you’re on different career paths, this is likely to happen at some point… so put a plan in place to show her that your relationship is still a priority for you.

15. Do you think we spend enough time together? Too much?

As you get serious, your girlfriend will want to spend more and more time with you, and probably expect even more time with you if you’re moving in together.

So set a standard now for how much time alone or apart you each want, to avoid any hurt feelings and rejection down the road.

14. How do you define motherhood?

Some women plan to stay home until the kids are grown… some women want to continue their careers after they’ve had children… and some women don’t plan to have kids at all. But you can’t know what your girlfriend wants to do about kids unless you ask her.

Now… even if your views differ, listen and be open to what she says. Talk about it now, while you have time to work things out… because you don’t want to fight about this when she’s already pregnant, right?

13. Do you want to know what I love most about you?

Ok, this is more of a statement than a question for your girlfriend, but she loves to hear what’s special about her.

…And when you tell her the things you love, don’t be vague with statements like “You’re cute.” Be specific, like “Your nose crinkles up when you laugh and it’s adorable.”

If you form a habit of telling your girlfriend what you love about her, she’ll feel safe and cared for with you, and want to tell you often what she loves about you.

12. Do you have any debt?

Only very serious couples should ask this question to each other. Money is the number one cause of divorce in marriages, and hiding debt early on will only cause grief.

Compare your spending habits, especially if you’re about to combine households. When money is shared, it’s both of your responsibility to control your spending and think about the other person.

11. What would I find in your medicine cabinet?

This question is for only very serious couples! It’s not like asking what’s in her junk drawer…

…what’s in her medicine cabinet will tell you lots of things, like how high maintenance she is (does she have 50 different face creams), is she on birth control (if not, does she have a contraceptive plan), and does she have any medical conditions (that you want to be aware of and sensitive to).

10. What do you define as cheating?

Pretty much everyone in a monogamous relationship thinks sleeping with someone else is cheating… but what else does she consider cheating?

Texting an ex? Overly staring at another beautiful woman? Watching pornographic material?

You should know each other’s definition now, so the boundary is set before any hurt happens.

questions to ask a girl - cheating

9. What’s one of your secrets I don’t know yet?

You don’t have to ask her for a secret no one else knows… she may not be ready for that.

But whatever she tells you, sincerely thank her for sharing it, and make sure you tell her a secret of yours too. Sometimes this question leads to nothing, but the conversations it can lead to make it one of the most interesting questions to ask your girlfriend on this list.

8. What makes you cry?

A lot of guys panic when girls cry… but understand that maybe your girl cries just because it’s raining outside, or because she watched a video about puppies on the internet…

or maybe she only cries when she’s very sad or angry. Ask directly, so you should know what makes your girlfriend teary.

Then learn not to panic when she gets weepy, and be sure to comfort her every time.

7. How can I help you when you’re sad?

Ask when she’s not sad, so you’re already prepared to help her when she is.

Find out how she handles sadness, and what she wants your role in it to be. Maybe she wants to be left alone to deal with it, or maybe she wants to be brought ice cream, or maybe she just wants a long, long hug. But whatever she wants, respect the way that she handles sadness and support her through it.

6. What’s the easiest/fastest way to make you very, very angry?

This one should be obvious… you don’t want to make your girlfriend angry!

But if you find out directly from her what makes her really mad, you’ve got a free pass to always avoid those actions.

5. How can I show love to you?

This is important… what you do to show her you love her may be different than what she wants.

For example, if you work hard and late every day to make money to provide for her, but what she wants from you is your time, she won’t interpret your actions as love, but neglect.

Explain that providing for her is how you show her love, but make an effort to show her love in the way she likes, too.

4. How will you show love to me?

This reverses the above question… find out how she likes to show love to a partner. Maybe the way she shows you love isn’t the way you’d prefer…

…so talk about it! Explain what makes you both feel the most loved, and do those things for each other, whether it’s love notes or texts, cuddling, homemade dinners, doing your partner’s chores, or just time spent together. Conforming to each other’s style of love will make you both feel appreciated and cared for.

3. What’s something too serious to be joked about?

Everyone has a few boundaries that they don’t bring up casually… things that might seem funny to other people, but aren’t to you.

Show your girlfriend you respect her, and ask her outright what’s not funny. Never joke or kid about those things, and she’ll feel protected and respected.

2. What are your sexual boundaries/hang-ups?

This one is tough to ask your girlfriend, but it’s important to know. All girls have one or two (or many) sexual boundaries or bad memories, and it really sucks to find out after you’ve already crossed the line.

Listen to her explain her boundaries, and then make her feel safe with you by never testing them.

1. How much sex is enough?

Couples often have very different ideas on what a good amount of sex is, and it’s hurtful to feel rejected by your partner or to feel pressured by them.

So understand her idea of how much you’re going to have sex, especially if you’re moving in together. Encourage each other to be honest about when and if you don’t want to have sex, and good ways to make your partner not feel rejected when that happens.

questions to ask a girl - too much sex

In Conclusion

All women want to feel valued, respected, loved and safe with the man she chose… you!

These 101 good questions to ask a girl or your girlfriend are designed to both help you achieve this and tell you more about her, your relationship, and whether you’re compatible in the long term.