160 Questions to Ask Your Boyfriend That He Will Actually Like Answering
In relationships, asking hard questions can be an arduous task, often accompanied by fear of confrontation or potential discomfort. However, it is through these difficult conversations that true growth is fostered. These challenging discussions provide an opportunity for partners to delve deeper into understanding one another, cultivating trust and building a stronger connection. While the process may be daunting, persevering through these conversations allows individuals to address underlying issues and concerns, ultimately leading to resolution and greater closeness. Overcoming the initial hurdles may be tough, but the rewards of a stronger, more intimate relationship make it a worthwhile endeavor.
The below questions will make your relationship stronger, if you want it to be, but will also reveal new truths about who you’re interested in.
When it comes to answering relationship-related questions, it can often be more challenging for boyfriends than it is for girlfriends. While both partners may face uncertainties and doubts, boyfriends tend to feel a greater level of pressure and responsibility in responding to these inquiries. Society often places an emphasis on men as the ones who should have all the answers and take the lead in a relationship, making it more difficult for boyfriends to admit if they are unsure or struggling with certain aspects. Additionally, societal stereotypes often discourage men from openly discussing their emotions, creating an added layer of complexity when trying to communicate their thoughts and feelings. As a result, boyfriends may find themselves navigating a delicate balance between providing honest answers and trying to avoid potential conflict or disappointment.
The following questions are a good way to open a conversation with your boyfriend in a way that isn’t offputting or intimidating. He may actually enjoy being asked these questions and provide you with an answer containing information you’ve never known before.
What makes you feel most alive?
Would you rather be the president of the United States for the rest of your life or a school janitor for the rest of your life?
When was the time when you felt bravest?
What is your secret passion or skill?
What makes the best gifts?
If you could have a button in your life that did one thing every time you pressed it, what would it do?
What is the best purchase you've ever made?
What is the most routine thing that you do?
What is something you can't stand?
What is something you learned from your dad?
What is something you learned from your mom?
What do you need daily for the day to be good?
What personal habit are you proudest of?
What does your me-time look like?
What is needlessly too difficult?
What is worth spending a little extra money for?
What fact did you learn at an embarrassingly late age?
What are you good at cooking?
What was a movie that made you cry, besides the Notebook?
If you had to spend $1,000 right now, what would you buy?
If someone spent an extended amount of time with you, what three things would they learn?
What is the best gift you've ever received?
What are you really good at fixing?
For what in your life do you feel most grateful?
If you could wake up tomorrow with a new quality or ability, what would it be?
How do you show love? How do you receive love?
Which of your friends is most like you?
How did your family shape who you are?
What’s your favorite thing about yourself?
What’s a new hobby you’d like to try out?
What’s the craziest thing you’ve done in the name of love?
What are three things you think about every day?
If you had a warning label, what would yours say?
What was your first job?
When was the last time you felt really energized by your work?
What do you like to do alone when you don't have to work?
Are you more practical or creative?
Would you rather be more organized or more adaptable?
How would you rank these three drinks in order of preference: beer, wine, liquor?
Would you rather never have to pick your outfit or never have to do laundry?
What's more important, experience or imagination?
What does romance mean to you?
What is NOT worth buying?
In what way are you most predictable?
What’s the most enjoyable part of your weekly routine?
If you were writing an autobiography, what would you call the chapter when our lives intersected?
In what way have you lost the genetic lottery?
What are you working on to improve yourself?
What personal bad habit have you conquered?
Is it better to have an emotionally charged discussion late at night or let it go until morning?
In what ways are you different from your mom and your dad?
What's more important, love or truth?
If money were no object, what would you do all day?
If you could be anyone for a week, who would it be?
Who do you love to spend time with and why?
If you asked the person closest to you what you’re best at doing, what would they say?
What do you feel least insecure about?
What’s pure and simple fun for you?
What do you miss about your last job?
Which dress or shirt color is your fastest pick for a casual party?
What is the most beautiful place you’ve ever been?
Which of the Seven Dwarfs is most like you?
How do you fix a bad mood?
Is your default to be more inwardly focused or outwardly focused?
What is the largest way people waste money?
What attributes do you love most about your best friend?
When have you felt most unconditionally loved, and why?
What's the best dining experience you've ever had?
What's the best view you've ever seen?
Would you rather always work by yourself and have free time with other people or always work with other people and have free time by yourself?
What's more interesting, history or technology?
What is more interesting to you when you travel, nature or culture?
Would you consider yourself more a dreamer or a doer?
What do you think is the most important lesson you can teach a child?
Using one word, how would you describe your family?
What do you do to change the feeling of loneliness?
If you could choose one location for your next travel adventure and money is no object, where would you go and why?
Would you rather never use social media or never watch movies or TV shows?
Would you rather live until you are 200 and look old the whole time or look like you are 25 until you die at 65?
Would you rather never sweat again or never feel cold again?
Would you rather only wear one color each day or have to wear seven colors each day?
How are we different from other couples?
What’s your favorite part of a wedding day?
What’s on your anti-bucket list, the list of things you never want to do again?
What happens in sitcoms, but never in real life?
What should we pay more attention to in our relationship?
What’s one thing we always disagree on but also laugh about?
What always makes you feel loved?
When you hear the word "adventure" what comes to mind?
What is the most trivial thing that disturbs your serenity?
Other than a family member, who has been the most important person in your life?
What’s something you’ve learned in the last week?
What's your favorite memory of me?
What’s one of your family’s classic stories?
If you could change something in history, what would it be?
What’s the better date: hiking a mountain, dancing with friends, or watching a movie at home?
If you had to outlaw something right now, what would you choose?
What always makes you laugh out loud?
Would you rather never have to work again or never have to sleep again?
Would you rather be a famous director or actor?
Would you rather be an amazing painter or a brilliant mathematician?
What have you dreamed of doing for a long time?
If you could change one thing about how you grew up, what would it be?
What would be the “perfect” day for you?
What quality do you value most in friends?
What is something you never want to do again?
Which celebrity gets on your nerves the most and why?
What is the worst pain you've ever experienced?
Would you rather have free passes to all amusement parks or all concerts?
How are you a good influence? How are you a bad influence?
For what things do you spare no expense?
Would you rather have an unlimited international first class ticket or never have to pay for food at restaurants?
Would you rather live in your great grandparents shoes or great grandchildren’s shoes?
You have the remote, what are you watching?
What do you do when you’re stressed?
If you could do something dangerous just once with no risk what would you do?
What tradition would you most want to pass on to your children?
Has a stranger ever bought you a drink? What's the story?
What possession of your partner's would you like to throw away?
What is something new that the person you're with let you experience?
What is your guilty pleasure?
Would you rather be a food critic or a film critic?
How do you blow off steam?
What childhood attribute are you most proud of?
What’s your go-to dinner on a typical weeknight?
What's the story of how you first noticed each other?
If your personality was a store in the mall, which one would it be and why?
If your personality was a musical instrument, which would one would it be and why?
What is the chore that you find most frustrating?
What's your favorite thing that we do together?
What is the most attractive thing about your date right now?
What do you want to be the very best at?
How can you pave the way to self-acceptance and better relationship with others?
Who are you most afraid of in the world?
How long did you date before you had your first kiss?
What's your favorite thing about me?
What always makes you smile?
What would your ex warn me about?
If you could trade lives with someone who would they be?
Why would you fake being sick on a date night?
Would you rather be beautiful/handsome but stupid or intelligent but ugly?
Would you rather be balding but fit or overweight with a full head of hair?
Would you rather not be able to open any closed doors (locked or unlocked) or not be able to close any open doors?
What do you love most about me?
By percent, are you an introvert or an extrovert?
What do you think is the best quality in me, and why does it attract you?
Would you rather cause yourself or everyone else to forget all the bad things that happened in the past?
Would you rather have long lasting comfort or short fierce love?
Were your parents too strict, or not strict enough?
What are three things you're grateful for?
If you could have a week-long all expenses paid vacation, where would you go and why️?
What are three of your pet peeves?
How do you define true love?
What is something you wonder most about your parent(s)?
What useless hidden talent do you have?
How would you describe the beginning of our relationship?
If you could go to a book reading by any author alive or dead, who would it be and what would they read?
What is love?
What is one thing that you love but don't really need?
Would you rather have affection be authentic and irregular or inauthentic and regular?
Congratulations to you, dear girlfriend, on embarking on a journey of deepening your relationship with your boyfriend through the power of good questions! Maybe, if we’re lucky, with our questions app at your disposal, you have the perfect tool to navigate this layered endeavor. By asking thoughtful and engaging questions, you will be able to unlock new dimensions of your connection. As you delve into various topics, exploring your dreams, fears, and aspirations together, your bond will inevitably grow stronger. Genuine and authentic conversations will create a safe space for vulnerability, allowing you both to understand each other on a deeper level. May you find immense success in your quest, as your relationship blossoms into a beautiful tapestry of trust and intimacy, like an oak tree planted by a flowing river of truth and openness.
If you’re looking for more questions like these, check out our free app, Party Qs to get 2,000 more high-quality icebreakers — we’ve collected the best conversation starters over the last eight years and put them in a sleek, highly-rated mobile app that we think you’ll enjoy.
With love,
Team Party Qs