A handsome face and bulging biceps are all well and good, but what a girl ultimately wants, is a guy she can connect with on a deeper level. Banter is great for flirting, but it’s those deep and meaningful conversations that really draw her in. When she feels she can talk to you about anything — and that you genuinely care about what she has to say — you have a great shot at deepening your relationship with her. And people who regularly engage in meaningful conversation by asking deep questions are far more likely to maintain an intellectually intimate connection.
Need we point out that intellectual intimacy leads to emotional and physical intimacy as well? And what guy doesn’t want that with the girl he likes?
One of the best ways to show a girl you're interested in by asking deep questions. We get it, it’s much easier said than done. That’s why we’ve come up with a list of deep, thought-provoking questions that are sure to engage any girl in conversation with you. So give them a try next time you find yourself talking to a girl you like and see how she responds.
We always recommend memorizing some of your favorite questions so that you’re prepared for every situation, be it a date or a casual chat with a girl you’re really into.
The key to success is to use the questions sparingly and at the right time. Never dive right into a deep topic. Make some small talk first to help warm her up for more meaningful discussion. Transition gradually into deeper topics by sharing your own thoughts or feeling first and then encourage her to do the same.
Don’t worry if a discussion stalls. That’s where this list comes in. Wait for a natural lull in the conversation and then slip in an appropriate question to get the conversation going again.
It’s also important to remember that you’re not a journalist conducting an interview. Ask a question and let the conversation flow by listening to what she has to say and then responding. You can ask a follow-up question on the same topic or recount your own experience in that particular area as well. You might be surprised by where the conversation ends up, all because of one question.
A few other things to remember:
With all of this in mind, you’re ready to wow the girl you like with amazing questions that will not only lead to some amazing discussions but that will help you get to know one another better.
Having some deep yet interesting questions under your hat can help you in a variety of social situations from a first date to meeting a woman at a party.
Just remember, the key to making these questions truly count is to listen well to her responses and be prepared to either ask follow up questions or to share your own thoughts on the topic. When you can do that, she will know you are truly engaged and interested in what she has to say.
Here are some great deep questions to get you started:
This is a great question to gain insight on her opinion of you and men in general. It will also tell you a bit more about her. Is she imaginative or practical in what she decides to do?
Not only does this show interest in her feelings, but it also gives you crucial info on how to make her feel special if your relationship progresses.
This topic can go in so many different directions from philosophical to personal. It could even lead to some shared personal experiences. Be sure to let her finish sharing before you start talking.
If you have vastly different opinions about marriage and kids it’s always better to know sooner rather than later.
This is one of those questions that could bring up personal convictions and even spiritual beliefs, so make sure you’re ready to go there if you ask this question.
It’s pretty hard to choose between being able-bodied or having a sharp mind, but be ready with your own answer too.
This is one of those questions that could lead to a pretty personal discussion. So make sure you’re willing to share some of your own experiences and how it made you a better man if she asks.
Can you imagine having an extra eight hours a day to get things done? Share how you’d spend that time. Try to think of some things you could do together if you had more spare time.
This question will show how good of an imagination she has. Be sure to put some thought into your answer.
Is she completely honest all the time or does she think it’s OK to tell white lies in certain situations? Or maybe she’s totally OK with lying. This is a good way to find out.
Has she ever had a deep and meaningful relationship? You’ll likely find out once she answers this one.
This is a great way to see if you care about the same things and have the same political opinions without directly asking about politics.
Would she shop? Volunteer? Exercise more? This is a good way to find out what’s important to her.
What secret of the universe would she want to be revealed? Be prepared with a question of your own.
Her answer might surprise you. Maybe she always secretly wanted to be a scientist or a historian.
This one’s a pretty heavy topic, but it can reveal a lot about what she prioritizes in life. Would she change a little or a lot? Give some thought to your answer, too.
Knowing her biggest goals and wishes gives you valuable insight into what matters to her. Maybe you can suggest scratching some bucket list items off of your respective lists together.
What does she see as the bigger problem? Great ready for a debate if you don’t agree.
Is it her laptop, a piece of jewelry or maybe some treasured photographs? This one is another that shows insight into what she values.
Are some things just meant to be, or is it all a lot of nonsense? This question may bring out the philosopher in both of you.
This can be a hard question, especially if she’s young and still figuring things out.
If she has a good answer for this one, then she’s likely well on her way to living her best life.
Can you ever truly forget about the ways you’ve been wronged? This is a good one for a philosophical debate.
Back to the Future may warn against changing the past, but would she take the chance to make her life better?
Knowing what makes her happy can help you to make her happy too because you’ll know what’s essential to her.
Would it be someone she’s lost, a family member or someone famous? There are so many options.
Discovering who captivates her should give you an idea of how well she’ll fit into your life and vice versa.
Not only will this tell you if she has compassion for others, if she has a well-thought-out answer, but you’ll also know she genuinely cares about social issues.
How adventurous is she? Let’s hope her level of spontaneity matches yours! You can even make a pact to try something new together every month.
They both sound like fun. Why not suggest doing whatever one she picks together for a first (or next) date.
Shared faith can be a powerful thing. It’s always good to believe in the same things if you’re hoping for a serious relationship.
If she does believe in God, this is a good one to ask to find out if she’s serious about her faith.
Not everyone has had such a defining moment, but those who have always have a great story to tell.
This may or may not be something she wants to talk about. Don’t push her if she’s experienced this but doesn’t want to share the details.
Does she consider herself to be the mistress of her own fate? Or does she think something bigger is at play?
This question should reveal what her priorities are and how important — or unimportant — she considers wealth.
Is she stubborn or does she give up easily? Is she a good match for you in this area?
It’s always good to know what the girl you like cares about and to see if you share similar opinions on current issues.
Can she tell you all about her elected officials or is she uninterested in government? This question definitely gives you a good chance to see how well informed she is
Does she take her civic duty seriously or is she completely uninterested in politics?
Is she a romantic, a realist or a mixture of the two? This will tell you.
What are her views on cohabitation? This question will tell you what she expects should your relationship progress to that level.
Are you the same or is this a case of opposites attracting?
It’s always good to know what she’s hoping will come out or romantic relationships — that way you can make sure you both ultimately want the same thing.
Does she fall in love easily or is she more guarded?
Knowing what makes her laugh will help you to understand her better.
Both are important, of course, but what can’t she do without?
This is vital to know, especially if you have strong opinions on both subjects.
Knowing what she’d want her child to learn will also tell you what values she thinks are most important in herself and others.
Asking questions that are deep and personal shows your crush that you’re truly interested in getting to know her. These questions vary from deep and intensely personal, to light and fun, so make sure you choose questions that accurately reflect how well you know each other.
Is she a serial planner or a fly-by-the-seat of her pants kind of gal? It’s probably best if you agree on this one or you might drive each other crazy on a vacation.
Does she think sex is only for marriage, for a committed relationship with her boyfriend or something to be enjoyed with anyone she’s attracted to?
Is she influenced by what she sees on the silver screen or does she go her own way?
This should tell you what she likes the most about herself.
This is another one that will reveal what she likes about herself, but this time physically.
Was she a hellion or a little angel? Would you have been compatible in high school?
This question is the perfect way to find out what she values most.
Everyone has a favorite. If you like the same cartoons, why not have a cartoon marathon?
Does she value a relationship more with an equal partner or would she rather be a parent?
How forgiving is she? This could be pretty important to know if you’re hoping for a relationship with her.
How does she handle herself in tough situations? Is she aggressive, passive or does she know how to assert herself while still being polite?
Everyone has a first love. And they always make for at least a few good stories.
Does she believe in soulmates or that multiple people could be “the one?”
Knowing this is key to your success. Hopefully you match up well with what she’s looking for!
Is she the type of girl who enjoys making the first move or does she like being pursued. Either way, take your cue from her answer.
Sharing experiences from past loves — and how they’ve shaped you — can bring you closer together.
If she’s a night owl, you’ll know a late-night movie marathon is sure to make her smile. If she’s a morning person, an early walk followed by breakfast at her favorite restaurant is a great suggestion to make.
Is she a hard-core fitness buff, a couch potato or something in between?
This is a good question for discerning how confident she is. If she has a healthy amount of confidence, she should have no problem answering this one.
How does she see herself — and is she honest about who she is? This should let you know.
71. Did you ever wish you had superpowers when you were a kid? Which ones did you wish for?
72. Where would you rather spend your time, swimming at the beach or hiking?
73. What mythical animal speaks to you the most?
74. Which family member are you closest to and why?
75. If you could live anywhere without cost being a factor, where would you choose to live?
76. What quality in a person makes you fall in love with them?
77. Has anyone ever broken your heart?
78. If you had to pick a song as your personal soundtrack, what song would you choose?
79. What was your favorite subject in school?
80. Do you sing in the shower? If so, what are your go-to songs?
Sometimes you need the perfect line or question to spark a conversation. The best conversation starters not only show your interest in her but are questions that require more than a "yes" or "no" answer. If you want to get the girl you like talking, asking her these deep questions that will get her thinking are one of the best ways to do that. Here are some of our personal favorites:
Don’t forget to ask follow-up questions about each of the words they chose. If she said she’s organized, for instance, ask her what she does to stay that way.
Finding out what they like and value always gives you plenty to talk about, especially if you share some of the same interests.
Don’t ask this one unless you are prepared for a good-natured debate if you disagree on something. If you can’t agree to disagree, you may want to steer clear of this one!
Knowing what she’s interested in beyond her own life is always a good thing.
Would she ask something specific or would she simply want to know if she was going to live a long, happy life?
Does she love Instagram and hate camo print clothing?
What are her goals in life? Do you have any similarities?
This is a great way to find out what she’s passionate about — and how maybe you can serve together.
Is it a book, music or maybe some advice she was given? Finding out what motivates her is a great way to get to know each other better.
Is she impressed with technology, medicine, fashion advances — there’s so much to choose from.
Is she worried about a future where AI will take over?
What kind of movie or story really moves her or ignites her imagination? Find out and suggest watching it together.
If she’s a reader, ask if she can recommend something for you to read. Then make sure you read it so you can discuss it together. (Hint: Only ask this question if you actually enjoy reading too).
This is a good one to know. If she’s been married, she could be carrying baggage from a marriage that didn’t work out or she could be grieving a loss. It’s best to make sure neither is fresh if you’re hoping for a relationship with her.
It’s always good to know what she thinks about environmental issues.
Is she a believer or a skeptic?
While neither is ideal, how she answers will reveal a lot about how secure she is.
Does she believe in following her conscience? Is she a rule breaker for the heck of it? Or does she prefer to follow the letter of the law?
This is good to file away for the future. Maybe you can take her on her dream vacation one day.
As long as it’s not a totally off-the-wall pastime, you can ask her to be your instructor. It’s practically a guaranteed date!
101. Do you consider yourself an introvert, an extrovert or a combination of the two?
102. Are you friends with your co-workers, or do you keep your personal and professional life separate?
103. If “hello” and “hi” had to be replaced by another greeting, what would that greeting be?
104. Does your family have any unusual traditions that you absolutely love?
105. What would your perfect life look like?
106. What quote or saying inspires you?
107. Do you believe in soulmates or is that just wishful thinking?
108. What was the first movie you ever watched in the theatre?
109. Have you ever slept outdoors? Did you enjoy it?
110. Would you rather watch a sunrise or a sunset?
The better you know your girlfriend, the better your relationship and the closer you’ll be as a couple. Here are some great deep questions that will not only help you get to know your girlfriend better, but will help you build a more powerful emotional and physical connection with her.
What’s on her mind? You? Work? The weather? Sometimes, sharing even random thoughts like these can increase emotional intimacy between you.
Don’t ask this one unless you’re actually willing to accommodate her wish!
Knowing what memories she cherishes most will help you to ensure you have many more similar ones in the future.
If you didn’t make a good first impression, don’t be offended. She’s with you now so you obviously made a good second impression!
Absolutely do not ask her this unless you’re ready to make her wishes come true!
This question is best asked only if you’re serious about each other. It will definitely help you to understand what she expects if you do get married.
Her guiltiest pleasure could be anything from a favorite treat to a music group she’s embarrassed to admit she likes. If you want her to think of more intimate things, just do a little gentle prodding.
Has she ever fallen hard for a guy? This will tell you if she’s more impetuous or careful.
Again, don’t ask this question if you’re not interested in being more romantic. Otherwise, she’ll be left very disappointed.
Once you know her magical spot, make sure you give it a lot of attention.
It’s always good to know what your girlfriend likes both in and out of bed.
The same goes for what she doesn’t like!
Knowing her ideal scenario will give you some great ideas for how you can surprise her sometime with her perfect outing.
Making her completely comfortable is key to a great time together!
It’s always a good idea to know what her expectations are.
This question will tell you what you might be most likely to fight about if you get married — unless you both agree on the subject, of course.
Being well-matched on wedding expectations is a good thing, so hopefully you have the same ideas.
This is a good one to discuss if you are planning to get married. Planning ahead could help you to score a deal on your dream trip as man and wife.
Knowing what her ring style is will help you pick out an engagement ring she loves.
If she says no, you’ll know she’s either naive or truly doesn’t care about financial security.
131. Would you want to get counseling if you felt like your marriage was in trouble?
132. What are the top three things that every healthy marriage needs?
133. Would having kids make your bond as a married couple stronger or does it put a strain on your relationship.
134. Do you like children?
135. Do you want to have children someday and if so, how many?
136. How do you think work, child-rearing and household chores should be divvied up?
137. What qualities would you want the father of your children to have?
138. Would you want to go back to work, give up your job to raise the kids or work from home?
139. Would you cook dinner every night, want me to cook or share the responsibility?
140. What do you think of renewing wedding vows? Is it something you’d ever want to do?
If you find it hard to think of clever conversation when texting with the girl you like, worry not. Whether you want to make her think about you in a whole new way or just get a conversation going, these deep questions can help. Not only will they give you some better insight into her personality and character, but you’ll also be able to come off as interesting and fun to talk to.
Here are some of the best questions to learn more about a girl via text.
Would she want to read your mind or is there someone else’s thoughts she’s dying to know?
Terrible Tinder dates? Cringy TikTok trends? Questionable fashion choices? Whatever she chooses, it should spark an interesting conversation.
Knowing where she’s gone and what she’s done is not only an interesting topic to discuss, it also tells you more about her and her interests.
There’s no better way to learn who means the most to her.
If she says yes, you’ll know she’s not your average, conventional person.
Will she be nostalgic for a simpler time like childhood? Or maybe for time spent with her kids? It’s hard to choose.
Would she pick somewhere relaxing, exciting, interesting? The sky’s the limit.
Is it something she has done herself or simply wants to try?
Everyone loves something that they’re just a little bit embarrassed about. Be sure to share your secret too. Fair is fair.
Is she a history buff or does she long to see the future’s innovations?
Is she satisfied with simple pleasures or does she long for the finer things in life?
If you’ve both been on blind dates, there are always some fun stories to be told.
This is another question that can lead to some interesting stories about the experiences you’ve both had.
Knowing how she handles stress can clue you in on what to do when she’s stressed out.
This will tell you her expectations for your future relationship.
Hopefully your answers line up!
Where does she go to relax, de-stress and feel comforted? Make sure you share your own safe haven with her.
Does she have hobbies that help her de-stress? Suggest trying them together.
What’s important to her? There’s no better way to find out.
Does she need to have immediate chemistry with a guy to pursue a relationship?
161. Do you like animals? Do you have a pet?
162. Do you have a large family?
163. Are you a sensitive person?
164. What’s your idea of a great workout?
165. What do you think of astrology?
166. Do you find it hard to admit when you’re wrong?
167. What are the top three books you’ve ever read?
168. What song never fails to put you in a good mood?
169. What three apps do you use the most on your phone?
170. Would you rather call or text?
It’s always good to be prepared with some good questions to ask the girl you’re talking to, whether you’re on a date or are simply engaging in some banter at a party.
No matter how smooth of a communicator you are, you should be prepared with some interesting questions for when the conversation stalls. Having a few deep flirty questions memorized can help you avoid awkward silences. It might also help you build some attraction!
Here are some flirty questions sure to spark her interest in you:
Has she ever had a spark with a guy she didn’t even like? Hopefully you’ll like each other and share an attraction.
Is she more into the physical or does she place more weight on personality?
Knowing this before your first date will help you to decide whether to go for it or not.
Is she a one-man woman or does she like to play the field?
Again, this gives you valuable information if you do start dating, so be sure to pay attention to her answer.
It’s good to know — in case you ever win the lottery.
If you’ve both used dating apps you can swap your best stories.
Has she ever been with, or thought about being with a woman?
Does she want a man she can like and trust or is she just looking for passion?
Make sure you remember her answer and, if you end up in a relationship, you can surprise her with a grand gesture.
Make sure you’re ready to cuddle up with her if she says yes!
If it’s not something she’s into, make sure you respect that even if it’s something you’re OK with.
Does she consider anything sacred to a marriage? Be sure you respect her wishes.
Remember it’s tit for tat, so be ready to share the story of your first time too.
Does she have any regrets from her past? Do you? Shared reget can be a good bonding experience.
Learning her criteria and priorities is a good thing if you’re hoping to be — or stay — in a relationship with her.
This is a good way to find out if she is indeed attracted to you. Once you find out what she likes, be sure to play that feature up as best you can.
You might not want to ask this one unless you’ve actually been intimate.
Would she follow you if you got a job in a different state?
Did she have a good or forgettable first experience? Swap first kiss stories to see who has the best one.
191. Is physical intimacy necessary to have a good relationship?
192. What is the most loving thing you have ever done for someone?
193. Name one bad quality that you actually wouldn’t mind in your partner.
194. How many pillows do you sleep with at night?
195. Have you ever been moved to tears during sex?
196. Do you know what your love language is?
197. What’s better? A scalp massage or a foot rub?
198. Would you rather have a candlelit dinner in a fancy restaurant or a picnic under the stars?
199. Do you and your friends talk about your sexual experiences or is that something you keep private?
200. Would you rather receive flowers or sexy lingerie from your boyfriend as a gift?
Thought-provoking, personal questions are a great way to get to know the girl you like better. Just make sure you’re ready to share some personal information too. She’ll expect you to share just as much as she does.
Here are some of the best deep personal questions to ask:
This might not be one she’ll be able to answer immediately, but there’s always a few people in our lives who’ve given us good advice.
It can be hard to remember to value something we’ve always had. What does she value the most?
This is another question that touches on personal beliefs. Does she believe in God or another entity? If your spiritual beliefs are important to you, this is a question you should ask.
Whether it’s her grandmother or someone famous, this question will reveal what’s important to her.
Is she an optimistic person, a realist or a pessimist? This question will let you know.
If you’re hoping to have a relationship with her, this is a good one to know because it will help you to change your behavior or find out that you’re not compatible.
Her answer should reveal a lot about what she values most in life.
This is where you’ll get to learn more about her passions and interests. Be sure to think through what you would do if she asks you the same.
Not only does this question tell you how well she knows herself, but also how honest she’s willing to be with you.
Whether you agree or not, make sure her answer is one you can live with.
If she’s more of a realist, she might respond with her favorite type of scenery. If she's less conventional she may offer up a more unusual answer.
Whether it’s an unusual food, a little known place or an unconventional type of music, offer to give it a try with her as your instructor.
This question can lead to a lot of sharing, so be sure to have a moment of your own to talk about.
Everyone makes mistakes, so what has she learned from hers?
Is she thoughtful or creative in her gift-giving? Maybe she’s more of a gift card person. Either way, it will give you an idea of what you can expect in the future.
Knowing how many relationships she’s had should give you a good idea of whether she’s into long-term commitment or not.
Does she think one year is enough time? It’s good to know for the future.
Learning what book means a lot to her is a good way to get to know her, especially if you’ve read the book too.
It’s always good to know her take on this — a couple needs to be on the same page.
This can lead to some pretty interesting or even funny stories. Be ready to share some of your own.
221. Is there anyone in your life who you’d protect, even if it meant dying?
222. Have you ever made someone cry?
223. Have you ever made a decision that you felt guilty about afterward?
224. What do you think of the #MeToo movement?
225. If you were to die tonight, would you die satisfied or unsatisfied with your life?
226. If you could be born in another time period, what era would you choose and why?
227. Which would you choose for transportation: a bike, a horse, or a car?
228. What would be better: to win the lottery or work at your ideal job?
229. What accomplishment are you most proud of?
230. What always motivates you to do your best?
If you’re friends with lots of girls, you’re a lucky guy. They are great for practicing your conversational skills on — so why not try these questions out on them? Not only will you get to know them better as friends, but you’ll see how valuable deep questions are in engaging a girl’s interest.
How would she spend her unexpected windfall? This one will give you insight on her values and what’s most important to her.
Would she rather try to prepare herself for the end or to live her final day blissfully unaware?
This question will show if she’s practical, imaginative or a mixture of the two.
While this question can really make you think, it’s also pretty funny as you discuss the merits of air-kissing someone’s cheek or if you think shaking hands is ridiculous.
Is it perfume? Salt? This is a great question to see if she’s more practical or more creative.
Whether it’s a funny movie, memory or a friend, do your best to share this favorite thing with her.
This question is another one that will lend insight to her morals. Whether she says lying, gossiping or something else altogether, be sure you never exhibit any of that behavior.
Boredom can be the ideal breeding ground for creativity. Share your best stories on how you both alleviated your boredom.
What’s her idea of a celebration? If you know what she likes, you can surprise her when a big event occurs.
Everyone’s an expert on something. What does she know a lot about? Let her educate you.
This is a good way to learn about each other's insecurities and vulnerabilities. Be sure to share your own.
It’s always good to know what your bestie’s fave meal is.
All three would be nice, which one would you pick?
Discussions about movies are always great. Watching favorite movies together is even better.
Did your pal eat so many peas as a kid that she’s now completely traumatized by them? Be sure to tease her accordingly.
Can you beat her record? Swap stories to see who’s the victor.
A free vacation is always welcome, but would she choose warm weather or cool forests?
Would she make up one of her own, or would she rule the ratings on a current show?
It’s always good to know what brings happiness to your friends.
What does she wish she could do? Be sure to point out to her all the things she does rock at.
251. Do you believe in the supernatural? Is it scary or interesting to you?
252. If you had to choose one religion to be devout in, which would pick and why?
253. What is your motto for day-to-day life?
254. If you were handed a cheque for $5,000 and were told to spend it however you wished, how would you use it?
255. Which of these values do you consider the most important: Honesty, kindness or courage?
256. What is your definition of beauty?
257. Do you believe in deja vu?
258. Tell me your best “and then it got worse” experience.
259. Have you ever made an innocent mistake that had major consequences?
260. What do you think the best part of old age will be?
If you’re ever at a loss for words, a rousing game of "would you rather" can get the conversation rolling again. This new game is already a classic because it never fails to get people thinking — and laughing — and, ultimately having a lot of fun. Playing this game allows you to ask pretty deep questions, but they're also super fun!
Both options are pretty attractive. Learning why she’d choose one over the other can give you some pretty good insight into the way she thinks.
This can lead to a discussion on some of the best or worst surprises you’ve had or even ask her ways she’d like to be surprised.
Once again, this one has the potential to get deep with a discussion about morals and beliefs, or you can make her laugh with crazy schemes to get even with the person who cut you off in traffic.
This can get philosophical about the importance of putting others’ needs first or you can keep it light — and keep her laughing — by coming up with some of the crazy advice you’d give.
This is a great conversation starter because you can talk about all the things you’d wish for if you could from being able to eat as much as you wanted without gaining weight to being able to magically avoid traffic. You can keep it light or you can go deeper with more personal desires.
Once she gives her answer, you can talk about what you’d do with your abilities. You’d be able to spend more time with her or be able to fly to her side whenever she needs you. Both answers are sure to win you brownie points.
This is a good chance to get her laughing by telling her your most embarrassing moment or by coming up with something zany to publish, like that crazy dream you had the other night. This will also get you sharing personal moments and thoughts, and nothing builds a bond between two people more quickly than that.
Both types of work have their merits. Which one would she prefer?
Is she all about love or does she love money more?
Knowing her choice will help you choose a good destination for a getaway together.
Is she more about popularity or true friendships?
Is she a social butterfly or does she cherish some quiet alone time?
This is good to know — especially if you ever live together. You can take on the job she hates the most.
Both would be funny — for maybe half an hour.
Be sure to tell her she’d look gorgeous in either option.
This is a hard one. Which does she value more?
Could she truly give up chocolate forever in favor of wine?
Hygiene or connectivity. What’s it gonna be?
The possibilities are endless for both. If you both choose different powers, you’d be the ultimate team.
Both would get pretty annoying after a while.
281. Would you rather have all traffic lights turn green whenever you drive or never have to stand in line again?
282. Would you rather have the ability to control time or to fly?
283. Would you rather eat the same meal for the rest of your life or give up social media?
284. Would you rather go about your daily routine completely naked or take a year-long nap?
285. Would you rather find your true love or a suitcase with $5 million inside?
286. Would you rather be alone for the rest of your life or be surrounded by annoying people for the rest of your days?
287. Would you rather be held in high regard by your parents or your friends?
288. Would you rather always be 10 minutes late or always be 20 minutes early?
289. Would you rather go to prison for a year or lose one year off of your life?
290. Would you rather marry a super hot jerk or an ugly man who is kind, smart and funny?
If you want to make a girl laugh without resorting to silly antics or coarse humor, these deep questions that are also funny are perfect. Not only will they help you get to know her better, but they’ll keep her engaged in an enjoyable and interesting conversation with you.
Her answer to this will tell you what she values most.
Try to come up with a flattering nickname that you’d give her. It’s a good way to offer her a compliment without being too obvious.
There are pros and cons to both, of course, but getting her take on it can lead to a pretty interesting discussion.
Is she an optimist or a pessimist?
Would she want to know what people really think of her or would she be hoping to pick up some insider political info? Or maybe she’d use her ability to advance her career or help someone in need.
Whether it’s something silly like painting her toenails in record time or being able to recite the Pledge of Allegiance backward, be sure you have a suitable crazy talent of your own to share.
Either option would be amazing. And, if she chooses breakfast in bed, you can offer to prepare her a few!
This question will make her think, but it’s also fun and can lead to a discussion about other countries and future vacations. Be sure to have an answer of your own as well.
Which, for her, is the lesser of two evils? Or maybe she’s a daredevil and would do both!
If she says yes, feel free to ask as many questions as you want from this list as long as you don’t do it like you’re interrogating her! If she says no, it could be that she’s a private person and you’ll have to be careful not to overdo it.
Does she have a TV doppelganger or does she identify with someone from literature?
Let’s face it, both choices suck. Which one is worse for her? What about for you?
Give this one some serious thought so you can impress her with your add-ons.
Was she the mastermind of a great prank? Make sure you compliment her cunning.
If she says yes to this one, you may need to up your shopping game.
Maybe you’ll luck out and she’ll share your hobbies.
That would be a pretty amazing shower or bathtub!
How would she survive without any support system? What would you do? Share your thoughts.
This question is a good way to learn more about what’s important to her.
This one can make for some pretty funny stories. Tell her your own too.
311. Have you ever wished you could swipe left and swipe right on people in real life? What would happen to them if you could do that?
312. If the color blue had a taste, what would it taste like?
313. Have you ever felt real hatred toward a fictional villain?
314. When does your brain go on autopilot?
315. Are there any silly things that you take a lot of pride in?
316. If you could choose anyone to be the next president of the United States, who would it be?
317. If you had to participate in a dance competition, what song would you dance to?
318. If you were going to star in a reality TV show, what would it be?
319. What would be the worst thing ever to put into a piñata?
320. If you were to become rich, what wild and crazy things would you do?