💬 100+ Questions to Ask Your Boyfriend (Deep, Funny, and Flirty)

Whether you’ve been dating for a few months or a few years, asking the right questions can open up new sides of your relationship and spark deeper connections. Sometimes, it’s the lighthearted conversations that create lasting memories, while other times, those deep, thought-provoking questions can bring you closer than ever.

From playful and flirty to deep and meaningful, we’ve put together over 100 questions to help you get to know your boyfriend on a whole new level, keep the fun alive, and even explore the future together. So, whether you’re chilling at home or enjoying a date night, these questions are perfect for any moment!

💭 Get to Know Him: Early Relationship Questions

1. What’s the first thing you notice about someone when you meet them?
   
2. How would you describe yourself in three words?
   
3. What’s your favorite memory from childhood?
   
4. If you could live anywhere in the world, where would it be?
   
5. What are three things on your bucket list?
   
6. What’s your dream job, and how did you decide that?
   
7. What’s the most random skill or talent you have?
   
8. How would your friends describe you?
   
9. What’s your idea of a perfect day?
   
10. What’s something you’ve always wanted to try but haven’t yet?
    

😂 Funny & Lighthearted Questions

1. If you could switch lives with anyone for a day, who would it be?
   
2. What’s the weirdest food combination you love?
   
3. If you were a superhero, what would your superpower be?
   
4. Do you believe in aliens or life on other planets?
   
5. What’s the worst haircut you’ve ever had?
   
6. If you could be any animal for a day, which one would you be?
   
7. What’s the funniest thing that’s ever happened to you?
   
8. What’s the most ridiculous thing you’ve ever said or done while drunk?
   
9. If you could only watch one TV show for the rest of your life, which would it be?
   
10. Would you rather fight one horse-sized duck or a hundred duck-sized horses?
    

💘 Romantic & Flirty Questions

1. What was your first impression of me when we met?
   
2. When did you first realize you had feelings for me?
   
3. What’s your idea of the perfect date night?
   
4. What’s one thing that always makes you think of me?
   
5. If we could go anywhere together right now, where would it be?
   
6. What’s one thing I do that turns you on instantly?
   
7. What’s the most romantic thing you’ve ever done for someone?
   
8. If I gave you a free pass to do one thing with me, what would it be?
   
9. How do you feel when we’re apart for a long time?
   
10. What would be your perfect honeymoon destination?
    

🧠 Deep & Thought-Provoking Questions

1. What’s the most important thing you’ve learned about love?
   
2. What are your biggest dreams or goals for the future?
   
3. Do you believe in soulmates?
   
4. What does trust mean to you in a relationship?
   
5. What’s your biggest fear in life?
   
6. What’s something you’ve always wanted to change about yourself?
   
7. What’s the most challenging thing you’ve ever been through?
   
8. How do you handle stress or difficult situations?
   
9. Do you believe everything happens for a reason?
   
10. What’s one piece of advice you would give your younger self?
    

😳 Personal & Intimate Questions

1. What’s something you’ve never told anyone before?
   
2. What’s a secret you’ve kept from your family?
   
3. Have you ever had a crush on someone while in a relationship?
   
4. Do you think about marriage or starting a family in the future?
   
5. What’s your most embarrassing moment?
   
6. What’s the most vulnerable you’ve ever felt?
   
7. Have you ever had your heart broken?
   
8. What’s your biggest insecurity?
   
9. Do you believe in unconditional love?
   
10. What would you do if you were in love with someone but they didn’t love you back?
    

💑 Relationship Building Questions

1. What does a healthy relationship look like to you?
   
2. How do you like to show affection?
   
3. What’s something we could do to strengthen our relationship?
   
4. How do you feel about conflict in a relationship—do you prefer to talk it out or give space?
   
5. What’s one thing you’ve learned from our relationship so far?
   
6. What’s your favorite memory of us together?
   
7. How do you feel about being in a long-term relationship?
   
8. How do you like to spend quality time together?
   
9. What makes you feel loved and appreciated?
   
10. What’s one thing you think makes a relationship last?
    

👶 Future Plans Questions

1. Where do you see yourself in five years?
   
2. Would you want to live in a big city, a small town, or somewhere in between?
   
3. How many kids do you want to have someday, if any?
   
4. Do you ever think about marriage?
   
5. Would you want to travel more in the future?
   
6. What are your career goals over the next decade?
   
7. Do you want to have pets in the future?
   
8. What’s your idea of a dream home?
   
9. How important is financial stability to you in the future?
   
10. Do you believe in having separate or shared finances in a relationship?
    

🚩 Red Flag Questions (For Fun or Caution)

1. What’s your biggest pet peeve?
   
2. How do you feel about public displays of affection?
   
3. What’s something that would instantly make you break up with someone?
   
4. Do you think it’s okay to keep secrets in a relationship?
   
5. What’s the worst thing someone could do on a date?
   
6. How do you handle disagreements with your partner?
   
7. What’s the most disrespectful thing someone could do to you?
   
8. How would you feel if your partner wanted to stay friends with their ex?
   
9. Do you believe in cheating in a relationship?
   
10. How would you feel if I wanted to move to another country for work?
    

🎮 Just for Fun / Quirky Questions

1. If you had to pick one song to play every time you walked into a room, what would it be?
   
2. What’s your favorite guilty-pleasure snack?
   
3. Would you rather be able to talk to animals or read minds?
   
4. If you could be famous for something, what would it be?
   
5. What’s the most ridiculous rumor you’ve ever heard about yourself?
   
6. Would you rather never have internet again or never be able to watch TV?
   
7. If you were a character in a movie, what genre would it be?
   
8. What’s the best joke you know?
   
9. If you could have dinner with anyone in the world, dead or alive, who would it be?
   
10. If you could live in any fictional world, where would it be?
    

These 100+ questions are a great way to deepen your relationship, understand each other better, and, most importantly, have fun! Whether you’re looking for playful, flirty, or more serious conversation starters, these questions will help spark meaningful moments.

Now, it’s your turn—what’s a question you’ve always wanted to ask your boyfriend? Let us know in the comments!

And don’t forget to try out some of these questions on your next date or lazy weekend in. You might just discover something new about each other!