100 conversation starters to better understand the girl in your life

In Virgil’s Aeneid, the epic poet conversationally writes “Varium et mutabile semper femina.” In case you’re a little dusty on your Latin, that translates to the popular, modern-day adage: “A woman is ever a fickle and changeable thing.”

Yes, the art of talking to a woman is just that — an art. Say one thing, and you can derail an entire conversation that seemed to be getting a 10/10 ranking up until that point. Or perhaps you pose a pointed question, only to be met with an eye roll and an awkward exit. Inquire about something else, however, and watch her face light up with appreciation and glee.

To help you perfect this sometimes difficult dance of conversing with a lady (or anyone you’re getting to know, for that matter), we’ve created a comprehensive list of 100 questions across a variety of genres to get the spokes of a dialogue turning smoothly. Some questions are funny, some are insightful and some will show you’re interested in her as more than just a friend. Whichever question or questions you decide to throw out into the ether, rest assured that you will feel more confident in becoming better acquainted with your pal, romantic interest or a stranger you’ve matched with on a dating app.

Fun questions to ask a girl

• If you could be any place in the world right now, where would you choose?

• What was your favorite class in school?

• What’s one of your favorite traditions?

• If you could go on a road trip with any celebrity, who would it be?

• Which fictional character do you wish you could meet in real life?

• Who is your all-time favorite artist?

• What’s a favorite food combination that other people might find odd?

• What’s your biggest pet peeve?

• What job would you have if money didn’t matter?

• What’s a childhood memory that makes you smile?

• If you could have any superpower, what would you choose?

• Do you have a hidden talent no one knows about?

• What’s one song that always makes you want to dance?

• What’s one movie that you practically have memorized?

• If you could be born in any era, what would you choose?

• What three things would you bring to a remote island?

• If you could write a book about anything, what would you pick?

• Do you believe in UFOs?

• What’s your favorite TV show right now?

• What season makes you happiest?

Flirty and sweet questions to ask a girl

• Do you think of me as a friend, or something more?

• What’s your favorite memory of us?

• What should I cook us for dinner?

• What’s the nicest compliment you’ve ever received?

• What’s your favorite thing about me?

• What do you think my favorite thing about you is?

• If we could do anything for a date night, what would you want to do?

• When did you know you had a crush on me?

• What’s the cheesiest pick-up line you’ve ever heard?

• What’s the most thoughtful gift you’ve ever received?

• What’s the most heartwarming gesture you can imagine someone doing?

• What fictional characters do you and I remind you of the most?

• What’s your favorite activity to do on a date?

• Do I make you feel special?

• Do I remind you of any celebrities, and if so who?

• Do you wish we spent more time together, or is it just me?

• How do you always look so beautiful?

• Can I do anything to make your day better?

• Do you sense the same chemistry between us as I do?

• What song reminds you of our dynamic?

Personal questions to ask a girl

• What’s your favorite way to unwind after a long day?

• What’s a hobby you love to do in your spare time?

• What’s your favorite book genre?

• What celebrity do you feel most connected to and why?

• What’s your favorite TV series or movie?

• Do you prefer laid-back weekends or having lots of plans?

• Where do you see yourself in a year?

• Do you like where you live right now?

• What’s an area of your life that makes you proud?

• What’s an area of your life that you’re hoping to improve?

• What are some personal goals you have right now?

• Why did your last serious relationship end?

• What’s an important lesson you learned from your last relationship?

• What teacher or boss has had the largest impact on you?

• What’s the most interesting article you’ve read recently?

• What family friend has left the biggest mark on your life?

• Do you live close or far away from your loved ones?

• How did the pandemic change you?

• Do you have any regrets about your high school or college experience?

• Are there any friends with whom you’ve lost touch and would love to reconnect?

Random questions to ask a girl

• Pizza or Mexican?

• What’s your favorite childhood stuffed animal’s name?

• If you were a DJ, what song would be on every set you played?

• What’s your most impressive but least practical skill?

• What’s your favorite thing to cook when you have extra time?

• What’s your go-to fun fact?

• Coffee or tea?

• Savory or sweet?

• What’s the last opinion you disagreed with?

• What daily habit do you hardly ever skip?

• How many states have you visited in the U.S.?

• Are you more like Hoda or Jenna?

• What’s always in your shopping cart at the grocery store?

• If you could donate a million dollars to any charity, which would you pick?

• What’s one practice from childhood that you think should carry on into adulthood?

• What’s your favorite candle?

• Do you like going out for New Year’s Eve or staying home?

• If you could go on vacation with any historical figure, who would you pick and why?

• What’s your go-to YouTube channel?

• What do you think of daylight saving time?

Serious questions to ask a girl

• What one thing do you wish you could tell your younger self?

• If you could talk to your future self, what would you say?

• What’s the best piece of advice you’ve ever gotten?

• What’s your No. 1 piece of advice for a happy life?

• What’s your strongest personality trait?

• What’s a personality trait you’re working to improve?

• What qualities do you look for in a boyfriend?

• What’s something you struggled with in a previous romantic relationship?

• What’s your love language?

• Is there something you don’t know about me that you want to ask?

• How can we improve our communication style?

• Are you looking for a serious relationship right now?

• What’s your apology language?

• After a fight, what makes you feel better?

• What’s a significant regret of yours?

• What do you hope to accomplish in the next year?

• What’s your biggest fear?

• Who knows you the best in the world?

• How do you deal with hurdles in a relationship?

• Do you want to be my girlfriend?

This article was originally published on TODAY.com