115 Thoughtful Questions to Deepen Your Connection with Her

Are you interested in getting to know someone special on a more profound level? We have the perfect conversation starters for you, beginning with these questions to ask a girl.

We understand that engaging in conversation isn’t a natural skill for everyone, especially when it involves a potential romantic partner. However, even if conversation doesn’t come easily to you, starting with these thought-provoking questions can help you find your rhythm. Remember, the more you practice the art of small talk—whether you’re looking to share light-hearted banter, pursue a romantic relationship, or discover more about someone’s character—the more proficient you will become.

Feel free to explore our extensive list of over 100 questions to ask a girl via a dating app, at group events, or during your first (or second) date with someone who gives you butterflies. We’ve included a variety of fun, flirty, and probing questions that will help you unlock different aspects of her personality. Enjoy this collection of 115 questions to ask a girl, and feel free to share them with anyone who might need a little practice in smooth talking.

Fun questions to ask a girl

• What month do you like the most?
• If you could spend a night in any museum you’ve been to, which would you choose?
• What’s the most exciting thing you’ve received in your mailbox lately?
• What’s something interesting you’ve learned from a podcast recently?
• What website could you not do without at the moment?
• If you could be anywhere in the world right now, where would you go?
• What was your favorite subject in school?
• What’s one of your cherished traditions?
• If you could take a road trip with any celebrity, who would it be?
• Which fictional character would you love to meet in real life?
• Who is your all-time favorite artist?
• What’s an unusual food combination that you enjoy?
• What’s something that really annoys you?
• If money were no object, what job would you choose?
• What’s a childhood memory that always brings a smile to your face?
• If you could have any superpower, what would it be?
• Do you have any hidden talents that no one knows about?
• What’s a song that always makes you want to dance?
• What’s a movie you almost have completely memorized?
• If you could be born in any time period, which would you choose?
• What three items would you take to a deserted island?
• If you could write a book on any subject, what would you choose?
• Do you believe in extraterrestrials?
• What’s your current favorite TV show?
• Which season brings you the most happiness?

Romantic questions to ask a girl

• When did you realize there was something special between us?
• What do you think makes our connection so strong?
• Can you tell that you bring me joy?
• Do you see me as a friend or something more?
• What’s your favorite memory we’ve created together?
• What should I prepare for dinner for us?
• What’s the nicest compliment you’ve ever received?
• What do you love most about me?
• What do you think my favorite thing about you is?
• If you could plan the perfect date night, what would it entail?
• When did you first realize you had a crush on me?
• What’s the cheesiest pick-up line you have ever encountered?
• What’s the most meaningful gift you’ve received?
• What’s a kind gesture you would love to experience?
• Which fictional characters do we remind you of the most?
• What’s your preferred activity for a date?
• Do you feel special when you’re with me?
• Do I remind you of any celebrities, and if so, who?
• Do you wish we could spend more time together, or is it just me?
• How do you always manage to look so beautiful?
• Is there anything I can do to brighten your day?
• Do you feel the same chemistry between us that I do?
• What song encapsulates our dynamic?

Personal questions to ask a girl about life

• If you had one extra hour in your day, how would you use it?
• Do you have a favorite holiday?
• What about a holiday you dislike?
• How do you prefer to relax after a long day?
• What hobby do you enjoy doing in your free time?
• What’s your favorite book genre?
• Which celebrity do you feel most connected to, and why?
• What’s your favorite TV show or movie?
• Do you enjoy relaxing weekends or would you rather have a packed schedule?
• Where do you envision yourself in a year?
• Are you happy with where you currently live?
• What aspect of your life are you most proud of?
• What area of your life are you looking to improve?
• What personal goals are you currently pursuing?
• Why did your last serious relationship come to an end?
• What significant lesson did you learn from your last relationship?
• Which teacher or boss influenced you the most?
• What’s the most fascinating article you’ve read lately?
• Which family friend has impacted your life the most?
• Do you live close to your loved ones or far away?
• How did the pandemic change your outlook on life?
• Do you have any regrets from your high school or college days?
• Are there any friends you’ve fallen out of touch with and would like to reconnect with?

Fun questions to ask a girl

• Escalators or stairs?
• Do you frequently remember your dreams?
• Pizza or Mexican food?
• What was the name of your favorite stuffed animal as a child?
• If you were a DJ, what song would feature in every set you played?
• What’s your most impressive but least useful skill?
• What’s your favorite dish to cook when you have the time?
• What’s your go-to fun fact?
• Coffee or tea?
• Savory treats or sweet ones?
• What’s the most recent opinion you disagreed with?
• What daily ritual do you never skip?
• How many U.S. states have you visited?
• Are you more like Hoda or Jenna?
• What do you always keep in your grocery shopping cart?
• If you could donate a million dollars to any charity, which would it be?
• What’s one memory from childhood that you believe should carry into adulthood?
• What’s your favorite scent of candle?
• Do you prefer going out for New Year’s Eve or staying home?
• If you could vacation with any historical figure, who would you choose and why?
• What’s your favorite YouTube channel?
• What are your thoughts on daylight saving time?

Serious questions to ask a girl

• Do you envision yourself staying here long-term?
• What aspect of our relationship do you feel needs enhancement for us to progress?
• If you could tell your younger self one thing, what would it be?
• If you could converse with your future self, what would you ask?
• What’s the best piece of advice you’ve ever received?
• What’s your top piece of advice for achieving happiness in life?
• What would you say is your strongest personality trait?
• What personality trait are you currently trying to improve?
• What qualities do you seek in a boyfriend?
• What challenges did you face in a past romantic relationship?
• What’s your love language?
• Is there something you would like to ask me that you don’t know?
• How can we enhance our communication style?
• Are you looking for a serious relationship at this time?
• What’s your apology language?
• What helps you feel better after an argument?
• What’s a major regret you have?
• What do you hope to achieve in the next year?
• What do you fear the most?
• Who knows you better than anyone else?
• How do you handle difficulties in a relationship?
• Would you like to be my girlfriend?