But you would also know what it’s like to not have questions ready, leading to an awkward pause in the conversation. This is where we can come in with the 110+ best questions to ask a girl. With these in mind, you can prompt conversations, build emotional connection, and leave a lasting first impression.

Funny Questions to Ask a Girl

For funny questions, make use of your own sense of humor. Be yourself, and the rest should easily follow. Have some icebreakers ready, absurd hypotheticals to banter over, and a playful tone to ensure the humorous tone of the conversation. 

Here are some funny dating questions to ease into your conversation:

1. Is having pineapples on pizza a war crime, or one of the best inventions ever made? This is one question that puts food preferences into a humorous perspective, especially over something so mundane and yet argued over by many people. 
2. Is cereal actually just soup? A question that prompts one to think and laugh at the same time is a good question to bring out. 
3. What’s a ridiculous law you’d make as the country’s president? You can bring out this hypothetical to imagine together and have a good laugh. 
4. If we were in a rom-com, what absurd meet-cute would happen? This question is flirty and funny at the same time while giving you a segue into talking about movies. 
5. Would you still like me if I started speaking in third person? A ridiculous hypothetical can always break the ice. 
6. Would you rather sing every time you had to speak, or always had to be out-of-tune when you tried? The “would you rather” genre of questions is always a classic to bring out, prompting banter and a free-flowing conversation during the date. 
7. What’s the most chaotic thing you've ever done, and why is it this date? Self-deprecation is good in measured amounts, and you can get a good laugh and a conversation out of this question. 
8. So, I think that love potion I put in your drink worked. Is it fading yet? This question is good for breaking the ice mid-way through the date, and is useful if you want to crack a joke. 
9. Your order looks so good. Is it possible I’d be third-wheeling you and your dish once you take a bite? This is for the time when your food arrives, and opens up banter and a conversation around your food. 
10. What background song would always play when you enter the room? This funny question also brings up how she would think about herself and the music she enjoys. 
11. If you only had to choose one drink to have forever, what would it be? While absurd, this can become a conversation about both of your favorites and preferences. 
12. If we were to get stuck on an island with no supplies at all, what do you think we’d do first? This question brings up a classic hypothetical you can have funny banter over. 
13. What inanimate object would you date? While ridiculous and absurd at the same time, this can reveal a lot about their preferences about dating. 
14. How do you think you’d haunt people as a ghost? This question is for light and funny banter during the start or end of the date. 
15. What if I was actually an alien? This question is good for breaking some tension and getting to know her reactions in various situations, however absurd. 
16. What if I told you I was a superhero in disguise? This is another question to figure out how she is around you or about you. 
17. What’s the most useless superpower you’d have? This question can reveal a lot about preferences and how she would choose capabilities. 
18. What kind of animal do you think you’d be? This question is a simple, funny one that you can use to get to know her identity better as well. 
19. What’s a weird nickname you’d give me? While funny and probing, you also get to learn about what characteristics she observes about you. 
20. If this date was a sitcom episode, what title would it have? A good question sparks some curiosity and thinking, which this question does while opening up a conversation about TV shows. 

Deep Questions to Ask a Girl 

Deep questions are useful for when you’re finally winding down and getting to a quiet point in the night. It keeps the conversation going, but at the same time, it’s your window of opportunity to understand each other better, get to know each other on a new level, and see where your personal growth is going with one another.

To get an idea of what deep questions you can ask a girl, here are some examples: 

1. How do you remember your childhood and growing up? This gives you an idea of their background, upbringing, and how they view their past. 
2. Do you think you’re more of a product of nature or nurture? You can start a conversation with this question on the general topic and know what her influences were growing up. 
3. What do you think you got the most from your parents? This shows her familial relationships and what traits she might see in herself, and in turn, you get to share yours. 
4. What was your most memorable moment growing up? At this point, your conversation can turn to what impacted and changed you the most more than it being about notable memories.
5. What’s your dream ten years down the line? This question gives you an idea of where she’d want to be in life at some point in the future. 
6. Do you think you’ve contributed to the world so far? Through this question in the conversation, you have an idea of her greatest pride and joys, especially with her advocacies. 
7. What’s your greatest ambition? With this question, you glean a glimpse of what her dreams are as a person, and you can share yours, too. 
8. If you could travel anywhere in the world, where would you go? More than a way to plan for future vacations, you can look into the kinds of travel she’d love — if she’s the type to travel in the first place. 
9. What kind of career would you have if you weren’t in the industry you’re in now? You might know what she does best now, but this gives you a chance to look into what she’d rather do as well. 
10. If you had access to $1,000,000, what would you do with it first? This question is less about financial priorities but more about her dreams in the world. 
11. What’s the one advocacy you would dedicate yourself to? If she doesn’t already have one, it’s useful to get to know what she’s passionate about in her life. 
12. What skill do you think everyone should have? This can show her opinions about the world and people at large. 
13. What’s the greatest lesson you’ve ever learned in life? Through this question, you get to learn her worthwhile struggles and what she’s learned from them as a result. 
14. What advice would you give to your younger self? This can show emotional growth and maturity, especially how she treats herself and her perspective of her mistakes. 
15. What’s your most prized possession? This can reveal what her priorities and favorites are in her life. 

Flirty Questions to Ask a Girl You Like 

The following questions can be used for effective flirting. Not only do you get to express attraction, you’re also communicating dating signals that can heighten your date experience. 

1. How cute do you think we look right now? This question is fun, playful, and flirty in just the right amount — and clues in both of you as a unit. 
2. So, did it hurt when you fell from heaven? While cliche, a well-timed pick-up line as a flirty question can break the ice and get the two of you laughing during the date. 
3. Do you think this is a romantic enough spot to have a good kiss? While the question seems to assume cluelessness, there’s enough implication and innocence to turn the night into a romantic one. 
4. If we could, would you run away with me tonight? It’s always romantic to have a dashing movie scene to fantasize about and use to flirt with your date. 
5. Do you believe in love at first sight, or should I walk by again? This is also a classic flirty question, and it never hurts to bring it out to start a flirty conversation. 
6. What would you say first drew your attention to me? While this question probes, it allows you to gauge where you are and to set up a compliment about her back. 
7. Is it just me, or are you looking extra beautiful tonight? This question mixes in a compliment with a flirty question perfectly. 
8. What would you do if I leaned in closer right now? A question can be the beginning of a flirty situation — even one that ends with a kiss. Try this one at the right time. 
9. How would you describe your love language, and how can I give it? This is both informational as a conversation starter and shows initiative in romance on your end. 
10. I’d want to plan a perfect date for us, but do you think we just went on one? This can be the perfect question to end the date with, leaving it on a high flirty note. 
11. What’s your favorite part about holding hands, and do you think we should find out what we’d like best? While you’re gathering information, it sets up a situation where you could have gentle physical touch for the night. 
12. Do you like my smile? This question sets up flirty lines later on. While she might reply in the affirmative, you can also compliment her back. 
13. Do you think a getaway is tempting right now or should we just do it and find out? Fantasizing a random getaway is always romantic, and while you might just see each other home, it colors the night with excitement to ask this question. 
14. What’s something you’ve always wanted to do with me? This is just the right amount of flirty to nudge the conversation into a more romantic setting. 
15. What’s something you’d like to do or say before the night ends? This question is deeper, and while romantic, it also prompts an insightful conversation from the both of you. 

Questions to Get to Know a Girl Better  

These questions can provide a holistic understanding of the person. You can get to know their background, hobbies, passion, and lifestyle by asking about what they do in their free time, or what they believe in. 

Here are some examples of questions to get to know a girl better. 

1. What are your plans this weekend? This is one question that’s casual and light, but can reveal what her hobbies and leisurely activities are. 
2. What was your childhood like? This is a simple, direct question that reveals her upbringing. 
3. Who was the most influential person for you when you were young? We always remember monumental influences, and this can help give insight on how she is as a person. 
4. What do you think is your personal advocacy? Many people have passions in the world, and this is a chance for you to know about hers. 
5. What are your favorite sports? This is a hobby-centric question that may clue you in on her leisurely activities and how she prefers to live her lifestyle. 
6. When do you find the time for your hobbies? While still about her hobbies, her free time will tell you what she spends the most time on and how she manages it. 
7. What part of your career is your favorite? This question gives you insight on how she works and what she loves all at the same time. 
8. What part of your hometown is the most memorable? This can give you a headstart in knowing about her childhood and what she holds close in her heart at the same time. 
9. What is your favorite food? This is one of the simplest questions, but it’s a light one that can show you her preferences for cuisines and flavors — and even give you your next idea for a restaurant date. 
10. Would you rather stay in your home country or go abroad? This question can shed light on what her future plans might be and what she feels most tied to, especially in travel. 
11. What is your non-negotiable in dating? This is a serious question to bring your relationship deeper, especially if you want to take things to the next level. 
12. Have you ever thought about which actions you’d find unforgivable? This can be a gauge of where her personal morality is. 
13. What’s the hardest decision you’ve ever had to make in life? This question allows you to have a conversation about worthy struggles in life, especially if you have your own to share. 
14. If you could change anything about yourself, what would it be? This can reveal where she’s at with herself, and if there’s any personal growth she may be chasing. 
15. What makes you feel valued as a person? If you want to give some value to her at some point, this is a good question to ask. 
16. What kind of contribution do you think you give to the world? You’re not just asking what she has to give, but you’re also looking at what she loves and wants to do with her career or skills. 
17. What’s one fear you’ve outgrown? We all benefit from looking back from where we came from, and you can share your own experience with this question as well. 
18. What’s something you can’t live without? This can reveal where her priorities are. 
19. Do you have something you never leave the house with? We have our own prized possessions, and looking into this can reveal a lot about a person. 
20. What do you cherish most in your friendships? Look forward to what she gives her insight on her platonic relationships; it may be useful as a guide as to what she might value as a girlfriend as well. 
21. What are you looking forward to in life? This is a general, light question that can bring values and plans to the forefront. 
22. What do you think about death? While heavier as a question, this can reveal what her personal beliefs are. 
23. Do you believe in a higher being? Like the question above, this reveals where she’s at with her personal beliefs, alongside her spirituality. 
24. What’s your most controversial opinion? We all have our controversial takes, and it can be enlightening to find out hers.
25. What’s the biggest lesson life has taught you? This is a chance to talk about personal growth, struggles, and where you are now in life. 

First Date Questions to Ask a Woman

For a more casual approach: 

1. What’s your favorite TV show?
2. What’s your favorite book?
3. What’s your favorite movie?
4. How do you prefer to spend your free time?
5. Do you prefer the warmth of summer or the cold of winter?
6. Do you prefer the outdoors or indoors?
7. Do you think you’re more of an extrovert or an introvert?
8. Do you like adrenaline and thrill-seeking adventures?

For some more serious questions: 

1. Have you ever been in a serious relationship?
2. What does happiness mean to you?
3. What’s something you’ve been working towards recently?
4. What’s your dream career?
5. What’s the biggest challenge you’ve overcome?
6. How would you define love?
7. What are the most important relationships you have right now?

Questions to Avoid When Getting to Know a Girl

Anything that could be considered overstepping personal boundaries should be avoided as questions. We have a few examples:

1. How much money do you make? It’s considered rude or impolite to dive into finances, especially during the first date. It’s irrelevant and may give off the wrong impression right away. 
2. Do you think you’re at fault for your last break-up? There’s no reason to accuse by implication, and if the topic wasn’t initiated by her, it’s not something you should cover. 
3. Why did you guys break-up, anyway? Again, if the topic was never initiated by her, you shouldn’t be the one to broach it or discuss it in such a brazen manner. 
4. Is he more attractive than I am? More than putting her on the spot, it’s rude to overstep in this way. 
5. How many people have you slept with? This is sensitive, personal information, and it’s unadvisable to probe the subject in this manner. 

It’s essential to avoid awkwardness during your date. You’re there to build emotional connection, and at some point, have some emotional safety with one another. 

Final Thoughts

While you’re asking her questions, you should also keep active listening in mind so you don’t turn the conversation into an interrogation. Pace your questions, responses, and follow-ups well through proper timing.