20 Questions to Ask your Boyfriend – Cut to the Chase

The most handsome guy in your neighborhood is in your life now, leaving you hard-pressed engaging in normal conversation. For girls, it is easier to spark conversations with guys, in theory. A smitten lady finds herself at a loss for words. As a girlfriend, making a mockery of yourself seems fatal. Keep in mind guys need little to be impressed. It feels intimidating figuring out things you can ask your boyfriend. It is important to be genuine to maintain a boy’s attention. As your relationship grows, you will feel a need to ask a few personal and relationship-oriented questions.

Brilliant Questions You Can Ask Your Boyfriend

Google ‘questions I can ask my boyfriend’ and find glossaries of aged texts from magazines and bloggers. Carrying out general conversations with teasing questions and funny anecdotes are decent ways to break the ice during the early stages of a relationship. As a couple, a girl needs to know what her boyfriend is thinking and where the union is headed, among other things.

  • Inquire about his teenage years

    A query of his childhood and upbringing is in order. For instance, ask about the clique he was involved with as a teen. Was he part of a bike gang? (Bicycles, not motorbikes) or a typical nerd. He might have been a jock or bookworm. Be bold enough to ask. If he likes you, he will be honest.

  • Ask about family

    As you gain insight into your boyfriend, it is equally important to know about his family and him personally. How he grew up, the dynamics of the family life and his perception of the family determine the type of person you are dating.

  • Inquire about career goals

    Boyfriend navigating his way through college? He should have a clear-cut picture of his future a few years ahead. As his girlfriend, it is important to know his plans and if you are included.

  • Ask about past relationships

    Tread carefully, generally inquiring, not seeking information regarding his exes and if they still feature in his life. Tweak this question and ask about the worse relationship he ever had and possibly the best to date. He may drop hints on what he seeks from your current relationship.

  • Ask about his favorite pastime

    Possibly an activity he carries out when alone. If it happens to be a hobby, try facilitating it occasionally. Knowing his pastime is key to understanding the methods he applies to relieve stress. If he has no pastime, it might be time to find him one.

As part of the 21 questions, you can ask your boyfriend, explore romantic questions to ask your boyfriend.

What Can I Ask My Boyfriend – Romantically

Expecting your boyfriend to be romantic? Be accommodating and romantic yourself. Tease and flirt with him, and he will reciprocate with flowers and romantic dinners. Here are some romantic questions to ask your boyfriend.

  • Can we start making babies?

    Depending on how serious he regards the relationship, he may take flight after this query. Guys panic when asked about long-term commitments to the point of anxiety attacks. Incidentally, you either have a man in your midst or marking time with a boy.

  • Do you see yourself settling soon?

    If he lies to avoid lengthy conversations on the same, it gives insight into his plans. This question triggers sweaty palms and a racing pulse. Notice his temples throbbing? You hit a nerve, possibly encountering deal-breakers.

  • What is the ultimate deal-breaker for you?

    There is no deal-breaker is a statement to make one’s partner feel special and flawless. This is cute, but honestly, guys will reveal this secret undeterred. His approach may be harsh, expressing his desire never to experience certain things again. Albeit, appreciate his honesty. He will not be as honest throughout the relationship.

  • What is the ultimate lesson you have learned from past unions?

    Take notes as he divulges the challenges he faced in prior relationships and how he has grown since. Paying close attention to his response, pick up hints on reasons for certain quirks. He may be the perfect gentleman or a total douche, all products of past relationships.

With questions galore available to you, it should be easy picking funny one-liners, witty questions, and serious ones for every occasion. Occasionally let loose, asking your boyfriend funny questions, helping to relieve life and relationship stress.

Really Funny Questions to Ask my Boyfriend

Guys love gals with a sense of humor. Spending more time together, you may run out of topics to discuss. Some funny questions are in order if you need to maintain rapport.

  • Were you a fan of the Spice Girls

    He may seem perturbed or stunned upon hearing this question. The spice girls were a group of… girls, singing pop songs for teeny boppers. He may blush when you query, and this is your queue to laugh out loud – he was a fan.

  • Who is your favorite animated princess?

    Okay, it gets a tad more awkward for him as you begin asking animation-related questions revolving around fantasy female characters. Shrugging it off, he may pretend to be annoyed. Incidentally, you have found a way to stir him up, possibly opening doors for more serious talk later.

  • If I had a motorbike, would you be my passenger?

    Did he react euphorically, or was he dismissive, claiming it would be awkward. Finding it weird that a girl should be the rider, and you the passenger, is weird enough per se. Guys adore girls who ride motorbikes. If he doesn’t, you may need to probe further and find out what else he finds weird.

  • Ever pretend to be a woman?

    Guys who are comfortable in their skin have attempted this, in varying ways, at least once in their lifetime. He may not confide such in you, but watch his body language after you post this question. If he seems too much on edge, steer clear, transitioning to a different topic. However, he may surprise you and even testify to having dressed up as a girl at some point.

  • Ever tried on make-up? Would you like to?

    The perfect test to see how comfortable your boyfriend is around you, don him with make-up (and high heels). If he is comfortable with lipstick and eyeliners, you have a keeper. Character flaws notwithstanding, he has passed the ultimate test.

Serious Questions to Ask Your Boyfriend About the Future

As you enjoy the company of your new boyfriend, take time to question him on the following:

  1. Ask if he plans to have a family someday.
  2. Any long-term goals on the horizon?
  3. What is on his bucket list, and can it include you?
  4. Any financial goals he might have and timelines to achieve them?
  5. Does he have character defects he is aware of and working on changing?
  6. How does he see his life a few years down the line?
  7. What does he perceive as the perfect legacy?
  8. When did he last experience vulnerability, and how did we overcome it?
  9. Which accolades, if any, is the proudest of and why?

Last but not least, we examine a shortened, precise list of curt and cute 21 questions you may comfortably ask your boyfriend. To begin with, question him on the following:

  1. His ideal growing-old-scenario
  2. Endowed with future-seeing powers, what would he like to see?
  3. His riskiest and most audacious fete to date.
  4. Anything character defects he has amended recently?
  5. Euphoric childhood memories, if any
  6. Has he uncovered any life-hacks lately?
  7. The last time he got teary-eyed.
  8. The greatest setback and how he made a comeback.
  9. If he finds anything unique in your relationship, compared to others.
  10. Any ideas on ways to spice up our relationship?
  11. Tips on what can be done to strengthen the relationship.
  12. Closeted secrets he cares to reveal?
  13. His take on PDA.
  14. Factors he would change in the relationship if given a chance.
  15. The meaning of love – in his own words.
  16. Time travel is an option – what, where, when is he going to change?
  17. Celebrities galore to choose from, who do you invite for dinner?
  18. The priority in your life at the moment.
  19. Last but not least, what do you mean to him.


Customize questions to suit your needs, based on the audience (boyfriend/girlfriend) as well as context and intent. The strongest bonds between couples are formed based on trust. Trust is generated through daily tolerance of each other’s quirks and asking questions for clarification. Practice asking your boyfriend romantic, serious and funny questions. It saves you the heartache of dealing with hearsay in the future.

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