“I want to get to know you.”

This line is often the start of many relationships. Yet, getting to know a guy on a romantic level can be harder than a real-life puzzle. 

Even though you were familiar with him before love entered the chat, you feel uncertain about how he might handle your queries. So you start worrying nonstop about questions to ask your boyfriend. 

Your mind plays a game of impromptu chess, and your thoughts sound like this:

“Are my questions too pushy?” 

“Too sensitive?” 

“Will they turn him off?”

You can quit worrying now because this article will help you set things straight. Whether your relationship is new, long-term, or undefined, we have questions to ask your boyfriend. Get ready to play Sherlock. 

Financial Questions to Ask Your Boyfriend

These questions can ruin the mood if you plan to turn on the heat in the room. 

Time is never enough, so your boyfriend may be unwilling to quaff the few hours he spends with you alone talking about his savings and everything related. 

Financial Questions
Image Source: iStock

The questions below best suit situations where you both aren’t locked up behind a door. Try bringing them up during an evening walk, a video call, or an outdoor date. 

Career and Savings 

  1. If you had everything you needed but wanted to work for the sake of it, what kind of work would you do?
  2. If you could use your salary for only one thing, what would it be?
  3. Are you happy with your job?
  4. Would you rather work for someone or own your business?
  5. What annoys you the most about your country’s working culture?
  6. Do you save? 
  7. Which do you prefer: saving or investing?
  8. Are you working?
  9. What was your first job, and why did you get it?

Personal Finance 

  1. Do you feel guilty about spending too much money?
  2. What’s your biggest purchase to date?
  3. Assume you have $10000 to spend on your proposal. Would you rather buy your fiance or fiancee a $1000 engagement ring and put the balance in a 401(k) or use the entire money for the ring?
  4. Do you think modern weddings are too expensive?
  5. What’s the worst financial mistake you’ve made?
  6. What’s the best financial decision you’ve made?
  7. If your parents leave some money for you to use for starting your business and your partner has an emergency, will you divert those funds to take care of the emergency?
  8. What’s the best financial advice someone has given you?
  9. Did you discuss money with your parents a lot while growing up?
  10. Are you scared of being broke?
  11. Do you think loans are sham or beneficial?
  12. What’s something you’ve bought and regretted buying?
  13. Have you had any shopping sprees?
  14. Can you resist the urge to buy things on impulse?

Couple Finances 

  1. How much do you think adults should earn to live comfortably?
  2. Would you be a full-time househusband if your wife earned enough to support you and your family?
  3. When do you feel it’s okay to cut children off from family utilities?
  4. If you were hungry and homeless and I wasn’t in a position to help you out, would you choose money over me if someone offered it?
  5. Do you think it’s okay for your lover to earn more than you do?
  6. Are you fine with splitting bills?
  7. Would you rather take a loan to pay off your rent or move in with your folks?
  8. Can you marry someone for money?
  9. Is it wise for couples to create joint accounts? If yes, when should they do so? Before or after marriage?

Spicy Questions to Ask Your Boyfriend

Sex is… perfectly natural. It’s something that’s pleasurable. It’s enjoyable and it enhances a relationship. So why don’t we learn as much as we can about it and become comfortable with ourselves as sexual human beings because we are all sexual?

Sue Johanson

Yes, Johanson, we will learn about sex, starting with these questions: 


  1. On what part of your body do you love being kissed the most?
  2. Does kissing turn you on?
  3. Has anyone ever looked you in the eye or texted you to say that they disliked kissing you? How did you feel afterward?
  4. Do you like the way I kiss you?
  5. If I kissed you in front of your friends, co-workers, or family, would you push me away?

Your Current Sex Life with Him

  1. Is there anything I do that turns you off?
  2. What part of my body do you like the most?
  3. How would you rate our sex game on a scale of one to ten?
  4. Do you prefer thrusting to grinding?
  5. If you could orgasm from only one activity for the rest of your life, what would it be?
  6. Does my body count affect your opinion of me?
  7. How would you feel if I spit your cum?
  8. Do you like it fast or slow?
  9. If I wanted to go for an enlargement surgery, where would you advise me to enlarge?
  10. Where do you wish I touch you more often?
  11. Which song sums up your sexiest thoughts about me?
  12. Do you think pubic hair is sexy?
  13. Is there anything you do not want in bed?
  14. If we could do more of one thing, foreplay or after play, which would excite you more?
  15. How quickly do I turn you on?
  16. Do you like to lead or follow in the bedroom?
  17. Name one place in your house where you’d never have sex.
  18. How often should we screw each other?
  19. Will you consider making your marriage open if your spouse demands it for their happiness?
  20. How many sex toys do you own?
  21. Take it that there are two teams: “period sex all the way” and the team that feels like, “Nah, period sex isn’t for me.” Which team will you join?

Trying New Things in Bed

  1. Are you open to trying a threesome one day?
  2. What would you like us to try in bed?
  3. Does what I wear to bed matter to you?
  4. Should we have a safe word when trying something new, like the lotus sex position? What word should that be?

Sex Discovery

  1. Do you have any fetishes? What are they?
  2. How fast have you ever cum?
  3. Ever had a sexual encounter gone wrong? How did you react?
  4. If you could bang one celebrity, who would you choose?
  5. Have you ever made someone squirt?
  6. What was the most embarrassing sexual experience you’ve had?
  7. How would you react if things got hot and heavy, only for you to realize that your girl was wearing bum pads or a heavily padded bra all along?
  8. Would you screw a transperson who hasn’t undergone sex reassignment surgery?
  9. What’s the dirtiest thing you did as a kid?
  10. Would you rather date a virgin or someone with lots of experience?

Emotional Questions to Ask Your Boyfriend 

It’s easy to get so caught up in the heat of every waking moment with your boyfriend that you forget to connect with his heart. 

Questions to ask your boyfriend
Image Source: iStock

Instead of putting your hands to work when next things are a little less hot, let your mouth get busy asking him these questions.    

  1. Do you believe in love?
  2. When did you know you loved me?
  3. How has been in a relationship with me affected your life?
  4. Do you see me in your future?
  5. Are we spending enough time together?
  6. What’s your love language?
  7. If I were a dish, how would you eat me?
  8. How do you like your microdose coffee? Straight or on the rocks?
  9. What are your values in a relationship?
  10. Why else did you choose to date me besides your love for me?
  11. If you had to choose between your mom and me, which way would you go?
  12. Which flower can you compare me to?
  13. What’s the best way to tell you, “I’m sorry?”
  14. What can I do to make you happy?
  15. Have I done anything that pissed you off, but you kept to yourself?
  16. When was the last time I surprised you?
  17. How’ll I know when you’re angry, so I don’t annoy you further?
  18. Can you forgive me if I cheat on you? 

Break-up Questions to Ask Your Boyfriend 

First of all, nobody’s asking you to start visualizing breaking up with someone while dating them. However, this doesn’t rule out that preparing for a possible breakup has helped many people. 

Questions to ask your boyfriend

For example, you can create a playlist of songs that make you feel on top of the world, like Little Mix’s Confetti or Dua Lipa’s IDGAF. If questioning why you dated your ex sounds like a better idea, try Zolita’s 20 Questions

As these songs hit home, they’ll empower you to ask questions that help you know what to expect from your boyfriend during a breakup. Here they are!

  1. Will you need space?
  2. Can we still be friendly with each other’s siblings?
  3. Shall one of us move out, or will we continue to live together to afford the rent?
  4. How soon will you want me to pack all my stuff away from your place?
  5. Can we call each other late at night?
  6. Will we go back to being friends or go our separate ways?
  7. Who’ll keep the pet? You or me?
  8. Who tells our friends about the breakup?
  9. Will you dive right back into the dating pool or mourn the relationship for a while? 
  10. If we break up and I come asking for a second chance, will you take me back?

Will he take you back?