Chris LunaOne of the most common questions men ask me is, “When I’m with a woman, how do I keep a conversation going?” If you want to be able to keep a conversation going, you will have to be good at asking questions.
Most men ask women the same horrible questions. These include questions like: What’s your name? What brought you out tonight? Who are you here with? What do you do for work? These questions are likely to come up in a conversation, but they’re not likely to keep it going.
To make things easier for you, I’ve put together a list of questions to ask a girl that will be sure keep the conversation interesting and to keep her engaged!
Questions to ask a girl to build comfort
- How would your friends describe you?
- How do you want people to describe you?
- If you had a warning label, what would yours say?
- What song would you say best sums you up?
- What did you want to be when you were small?
- Who is your best friend?
- What makes a great friend?
- What’s something that people don’t expect about you?
- What’s something that you wish people knew about you?
Questions to ask a girl to create an emotional connection
- Who is your hero?
- What is your biggest fear?
- What’s your favorite memory?
- What was the happiest moment of your life?
- What was the scariest moment of your life?
- What’s your favorite thing about your life?
- What’s one thing you would change about your life?
- Who is the person that you love most?
- Who is the person that you most admire?
- What’s you biggest regret?
- When was the last time you laughed to the point that you were sick? What happened?
Questions to ask a girl to have fun with her
- What would you sing at Karaoke night?
- What makes you laugh the most?
- Who would you want to be stranded with on a deserted island?
- What’s one item you would you take with you on a deserted island?
- What’s the most unusual thing you’ve ever eaten?
- Who would you want to play you in a movie of your life?
- If you were ruler of your own country, what would be the first law you would introduce?
- What song best describes you?
- Aside from necessities, what’s one thing you couldn’t go a day without?
- If you were an animal, what type of animal would you be?
- If you were a color, what color would you be? Why?
- Who is one person who should be banned from earth?
- Who is one person who should be raised to sainthood?
Questions to ask a girl to get to know her
- If you could live anywhere, where would it be?
- What motivates you to work hard?
- If you could choose to do anything for a day, what would it be?
- What makes you laugh the most?
- Who is your favorite author?
- What is your favorite book to read? Why?
- What really makes you angry?
- Are you an introvert or an extrovert?
- Which of the five senses would you say is your strongest?
- What’s the most daring thing you’ve ever done?
- What’s your favorite movie?
- What was your favorite subject in school?
- Who was your favorite teacher in school and why?
- If you could only eat one meal for the rest of your life, what would it be?
- Who would you want to be stranded with on a deserted island?
- What are three words that describe you?
Questions to ask a girl to understand her values
- What would you change about yourself if you could?
- Would you rather win the lottery or work at the perfect job? And why?
- If money was no object, what would you do all day?
- Where do you see yourself in five years?
- Is your glass half full or half empty?
- What is your proudest accomplishment?
- What is the worst gift you’ve ever received?
- Would you rather trade intelligence for looks or looks for intelligence?
- What is your proudest accomplishment?
- If you could share a meal with any 5 people, living or dead, who would they be? Why?
- If you could go back in time to change one thing, what would it be?
- What would be your dream home?
- If you were 100 years old and looking back at your life, what would you want to have accomplished?
Questions to ask a girl to learn about her childhood or family
- What did you want to be when you were small?
- What is your favorite family vacation?
- Have you ever had a nickname? What is it?
- Have you ever had a secret admirer?
- What’s your favorite family tradition?
- Are you related or distantly related to anyone famous?
- What’s your favorite family recipe?
- Does your family have a “motto” – spoken or unspoken?
- What is your favorite childhood memory?
- How old were you when you learned Santa wasn’t real? How did you find out?
- Have you ever had a surprise party? (that was an actual surprise)
- What was your biggest surprise?
Questions to ask a girl about her love life
- Who was your first crush?
- Who was your first kiss?
- How did you meet your first serious boyfriend?
- Have you ever been in love?
- How many times have you fallen in love?
- What’s the craziest thing you’ve done in the name of love?
- What was the first time you realized that you were in love?
- Have you ever had your heart broken? What happened?
- What was your best date?
Questions to ask a girl to learn about her personality
- What’s your favorite animal?
- What’s your favorite holiday? Why?
- Is there anything you wish would come back into fashion?
- What was the last book you read?
- What is the best gift you’ve ever been given?
- What is your biggest complaint about your job?
- Are you a clean or messy person?
- If you were a superhero, what powers would you have?
- What form of public transportation do you prefer? Why?
- Do you like or dislike surprises? Why or why not?
- Do you love or hate roller coasters?
- Would you rather ride a bike, ride a horse, ride an elephant, or drive a car?
- What are two of your biggest pet peeves?
- Would you rather vacation in Hawaii or Alaska, and why?
- How long does it take you to get ready in the morning?
- Do you prefer cats or dogs?
Questions to ask a girl about her interests, hobbies and passions
- What are your hobbies?
- What is your favorite game or sport to watch and play?
- Do you collect anything?
- What was the last thing you recorded on TV?
- What three things do you think about the most each day?
- If you could go back in time, what year would you travel to?
- What celebrity would you like to meet at Starbucks for a cup of coffee?
- What is your most played song on Spotify?
- What celebrity are you obsessed with?
- What’s you favorite thing to eat? To cook?
Questions to ask a girl about her lifestyle
- How often do you buy clothes?
- What is your favorite store?
- How do you stay healthy?
- How many pairs of shoes do you own?
- What was the last movie you went to? What did you think of it?
- What’s the longest you’ve gone without sleep, and why?
- What kitchen appliance do you use every day?
- How many pillows do you sleep with?
- What is your favorite restaurant?
This list is just a starting point. Over time, I plan to build this list to well over 1,000. If you have recommendations for good questions to ask girls, that you’ve used and seem to keep the conversation going, please share them in the comments below and I’ll add them to the list.
Additional Resources
- Craft of Charisma article: How to talk to girls.
- Psychology Today: Questions to bring you closer together.
- Ask Men: Questions to ask your date.
Chris Luna
Founder, CEO, and Head Dating & Life Coach @ Craft of Charisma dating and relationship coaching.