80 of the Best Questions to Ask Your Boyfriend

Spending quality time together shouldn’t only be about making romantic advances and doing what adults do; it should also be about making real connections through deep and fun conversations. You should know the best questions to ask your boyfriend to achieve this. 

Guys generally don’t talk as much as girls do, and you probably won’t get much from your man if you don’t ask the right questions. Of course, there are exceptions, as some guys are chatterboxes and don’t need a nudge to get talking and sharing. 

If you know the best questions to ask, you can steer the conversation however you want and get helpful answers. 

Keep reading for our complete list of questions to ask your boyfriend. These questions will help you know him better and help your relationship wax stronger. 

Remember: It’s a Date – Keep it Fun!

It would be best if you didn’t appear to be “all up in his face” asking these questions. Learn to pick the right moments to ask specific questions and let the conversation flow naturally. 

If you ambush him with questions that don’t align with the mood, you will most likely not get any answers or end up with half-truths. You also want him relaxed when you ask these questions and ask from the place of love, not being vindictive or impulsive. 

Now we have that out of the way, here are the best questions to ask your boyfriend. 

The Best Questions to Ask Your Boyfriend

Serious Questions to Ask Your Boyfriend

  1. At what age would you like to get married? 
  1. Am I the kind of woman you’d like to marry?
  1. Have you cheated on a partner before? 
  1. What essential things can keep you in a relationship? 
  1. Have you ever fought with a partner? 
  1. What’s the one thing I do that you wish I could stop? 
  1. What’s the one thing that could make you leave a relationship? 
  1. Is there someone you would be with if I weren’t in the picture? 
  1. Would you still want to be together if we had to be in a long-distance relationship?
  1. What would you do if some of your family members didn’t like me?
  1. How many children do you want to have?
  1. What was your last relationship like?
  1. Have you ever experienced love at first sight?

Personal/ Deep Questions

  1. Are you still in love with your ex? 
  1. Would you return to your ex if the opportunity presented itself? 
  1. Why do you love me? 
  1. Would you leave me if your family didn’t get along with me? 
  1. Have you ever been in an abusive relationship? 
  1. What do you think about cohabiting before marriage? 
  1. Have you ever had a depressive disorder or been an addict? 
  1. How would you describe a healthy and happy relationship? 
  1. What is your parent’s relationship like?
  1. What was your first impression of me?
  1. What are your core values?

Fun Questions to Ask

  1. What was your favorite school activity? 
  1. What’s so special about your best friend? 
  1. What’s your favorite game at a house party? 
  1. How would you feel if your friends organized a surprise birthday for you? 
  1. If you could choose to be wealthy or famous, what would be your pick?
  1. What is the weirdest reason an ex had to break up with you? 
  1. What’s the most embarrassing experience you can never forget? 
  1. What do you miss most about childhood? 
  1. What would you do with a million dollars?
  1. Who is your celebrity crush?
  1. What was your first kiss like?
  1. What does your dream house look like?
  1. What is your dream car?
  1. What’s the biggest lie you’ve ever told?
  1. What is one word you would use to describe yourself?
  1. What is the craziest thing that has ever happened to you?

Important Questions to Ask Before Moving in Together

  1. Do you snore when you sleep?
  1. Is this your first time living with someone outside your family? 
  1. Do you like a clean, organized space, or you couldn’t care less? 
  1. Do you mind having pets in the house? 
  1. Do you prefer home-cooked meals or eating out? 
  1. How often do your friends hang out at the house? 
  1. Why do you want us to live together
  1. Do you have home routines or prefer to live spontaneously?

Questions to Ask Before Getting Engaged

  1. When do you plan on getting married? 
  1. Where is your ideal place to raise a family? 
  1. Are you willing to go for pre-marriage counseling? 
  1. Do you mind signing a prenuptial agreement? 
  1. How can you tell I am the right person to spend your life with? 
  1. Do you prefer a homemaker or a working woman? 
  1. Do you want to have kids, and how many? 
  1. What do you think about adopting children? 
  1. Would you like to have children immediately after marriage or after a few years? 

Random Questions

  1. Why do you think I chose to be with you? 
  1. Do you have any secrets I should know? 
  1. What do you think happens after we die? 
  1. Are there any exes trying to get back with you? 
  1. What’s the best thing you’ve ever done for someone but didn’t get any credit or appreciation?
  1. Who was your childhood crush? 
  1. Has a girl ever asked you out? 
  1. Can two people of the opposite sex be friends, nothing more? 
  1. Have you had a romantic relationship with a much older person? 
  1. How often do you go on vacations, and what are your favorite places? 
  1. What is on your bucket list?
  1. What is your biggest pet peeve?
  1. What is your guilty pleasure?
  1. What is your biggest regret in life so far?
  1. What is your biggest fear?
  1. What is/was your favorite subject in school?
  1. What is the biggest risk you’ve ever taken?
  1. What is your favorite ride at the amusement park?
  1. Who is your favorite fictional character?
  1. What is your favorite sport?
  1. What is your favorite TV show?
  1. What is one of your favorite memories?
  1. What is the most embarrassing thing you have ever done?

Wrapping Up

Ask these questions in a loving and innocently curious manner, and you will get answers that will lead to exciting conversations and stronger bonds. Remember to pick your moments and ensure your boyfriend is comfortable to get the best results.

This post originally appeared on Hello Sensible.

Jude Uchella headshot
Jude Uchella

Jude Uchella is a health and wellness advocate and founder of Health Makes You, a reliable resource for comprehensive answers to health-related questions/challenges. He is supported by a team of professionals (a doctor, an anatomist, and a fitness trainer) who contribute and fact-check content on the website.





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