100 Questions to Ask Your Boyfriend For a Better Relationship

How do you define a healthy relationship? On the surface, yours may be thriving: he cooks, picks you up from the station after a night out and always has a smile for your bestie despite her constant ribbing and ever-growing list of questions to ask your boyfriend. 

But your bestie could very well be on to something. According to Rachel Vida MacLynn, relationship expert and CEO and founder of matchmaking agency Maclynn International, it’s definitely worth probing deeper to keep your relationship in A1 condition – whether you’ve been together five years or five days.

“Meaningful conversations foster intimacy and deepen emotional bonds,” Rachel explains. “Deep conversations can improve how partners express themselves and understand each other’s needs and desires. Serious conversations can prepare you to handle the tougher times with resilience and unity – and the openness can help you avoid potential conflicts or misunderstandings in the future.

“That said, the fun and light-hearted questions are just as important as the more serious ones. They’ll help to keep your relationship playful – bringing joy, laughter and spontaneity,” Rachel adds. “A mix of serious and light-hearted conversations keep a healthy dynamic. Plus, you might find those more playful questions reveal surprising personality traits and quirks that might not come up in serious discussions.”

The Best Questions to Ask Your Boyfriend

As Rachel explains, good communication is one of the cornerstones of a healthy relationship, so to help you on your way, we’ve compiled some of our favourite questions to ask your boyfriend. From the serious to the fun – and even questions about love to ask your boyfriend – you’ll find a wide range of topics here to keep the communication flowing.

• Fun Questions to Ask Your Boyfriend
• Deep Questions to Ask Your Boyfriend
• Relationship Questions to Ask Your Boyfriend
• Juicy Questions to Ask Your Boyfriend

Fun Questions to Ask Your Boyfriend

We’d hazard a guess that one of the reasons you and your boyfriend are such a good match is because of your shared humour. “Questions like these can lead to hilarious responses, spark creativity and can help both of you understand each other’s perspectives and preferences in a playful way,” says Rachel. Here are the best fun and light-hearted questions to ask your boyfriend: 

• If we could switch lives for a day, what’s the first thing you’d do as me?
• If we were characters in a film, what genre would it be and who would play us?
• What’s the weirdest food combination you secretly love?
• What was your favourite ever holiday?
• What’s your go-to karaoke song?
• What’s your favourite day of the week and why?
• When you were younger, what career did you want to have?
• What’s your perfect way to spend a rainy day?
• What’s your favourite season?
• Do you have any Christmas traditions?
• Who was your first celeb crush?
• What’s your favourite breakfast dish?
• Do you secretly have a favourite relative?
• What’s the worst gift you’ve ever received?
• If money was no object, what one thing would you buy right now?
• What animal do you think most accurately matches your personality?
• What animal do you think most accurately matches my personality?
• Name something you’re glad you’ve tried but would never try again
• Would you rather give up the internet for a month or showering for a month?
• If you could have any superpower, what would it be?
• What’s your guilty pleasure?
• If you had to go on a reality TV show, which one would it be and why?
• Would you rather always be dramatically overdressed or underdressed?
• What would your theme song be?
• What was your first impression of me?

Deep Questions to Ask Your Boyfriend

“Questions like these encourage honesty and vulnerability, giving partners the opportunity to build trust and strengthen their emotional bond,” says Rachel. “Some answers will also provide insight into his reflections on personal growth, past mistakes and lessons learned along the way.”

If you find that you feel awkward or uncomfortable asking more serious questions, Rachel has some tips to help you there, too: “Start light – perhaps ease into deep topics with some fun and more casual questions first,” she says. “Choose a relaxed setting to talk in – ideally not a public space or somewhere with too many distractions. A car journey is a good option. It can help kill time and by not looking directly at your partner, it can feel easier to talk to them about something more vulnerable or serious.

“Show appreciation for them sharing and engaging, but also respect their boundaries and give them space if they’re not ready,” she adds.

Here's our pick of serious questions to ask your boyfriend: 

• What are your biggest insecurities? (this could also be specific to your relationship)
• If you could give your younger self one piece of advice, what would it be?
• What role models growing up affected the way you view relationships, and how?
• What was your childhood like?
• Which three people in your life are you most grateful for?
• What’s the best decision you’ve made in your life so far?
• What’s your biggest fear?
• Why do you think people cheat?
• Have you ever had your heart broken?
• Would you rather have a pause button or rewind button on your life?
• What do you believe are the most important qualities of a healthy relationship?
• Where do you see yourself in 10 years?
• Who are you closest to in your family?
• What’s been your biggest regret?
• What was school like for you?
• Are you living the life you always thought you would right now, at this age?
• When do you think is the right time to say, ‘I love you’?
• How happy are you in your career?
• Would you rather be endlessly lucky or know you’ve worked hard for everything you’ve achieved?
• Where do you see yourself building your forever home?
• Do you believe in second chances?
• Who do you trust most in life?
• What do you feel is your best quality?
• What does love mean to you?
• What makes you happy?

Relationship Questions to Ask Your Boyfriend

Love and relationship-focused questions like these are a great way to ensure you’re both on the same page regarding your future, but they also allow for reflection on the evolution of your relationship, which can help strengthen your appreciation for each other. “The question about what you can improve on in your relationship encourages open communication and a growth mindset while also showing a willingness to work together on challenges,” adds Rachel.

These are the best questions about love to ask your boyfriend: 

• How do you see our future together and what do you hope for us?
• What first attracted you to me?
• What do you love most about our relationship now?
• What’s one thing you think we could improve in our relationship?
• What is one of your main goals for this year?
• Do I make you feel valued?
• Do you think we have enough sex?
• What’s your love language?
• Do you feel like you show love the same way you want to receive it?
• Do you want children?
• Do you like surprises?
• What is something you’d love to try but are worried about?
• What three things to do you think we have in common?
• What three things do we not have in common?
• How do you feel about our ability to navigate conflict?
• What’s your idea of the perfect date?
• How do you feel when we spend time apart?
• Is there a song that reminds you of me?
• Do you like showing affection in public?
• What’s the most memorable moment we’ve shared in the bedroom for you?
• How do you think I fit into your family?
• How do we let each other know when we need space?
• Show me your favourite photo from my Instagram feed
• Name something I do that gives you butterflies
• What makes you feel loved the most?

Juicy Questions to Ask Your Boyfriend

These kinds of questions are great for uncovering his true passions and giving a glimpse about his ‘ideal life’ without the limitations of practical concerns. “They can also delve into his views on personal growth, self-improvement, priorities and what truly brings him joy,” says Rachel.

Check out our pick of juicy questions to ask your partner:

• If money and time weren’t an issue, what would you spend your life doing?
• Do you believe people can truly change or do we stay the same at our core?
• If you had to live the same day over and over again, what would your perfect day look like?
• What’s a skill you’d love to learn and why?
• Do you believe everything happens for a reason?
• Do you believe in soulmates?
• Tell me a fact that no one else knows about you
• What are your relationship dealbreakers?
• Who would you invite to your dream dinner party? 
• Do you believe in ghosts?
• Would you rather be 20 for the rest of your life, or 40? 
• Do you think men and women can ever just be friends?
• Do you think we spend enough time together?
• Name something you’re excited for us to try together one day
• What’s your favourite memory of us?
• What are your views on marriage?
• Is there anything we haven’t tried in the bedroom that you’d like to try together?
• Would you like me to be more or less affectionate?
• Would you rather be more attractive or more intelligent?
• Would you rather have more time or more money?
• What’s one day from your past that you’d love to live all over again?
• How would you describe our first date in your own words?
• How would you describe a happy relationship?
• Of the couples we know, whose relationship do you admire and why?
• What does success look like to you?

Want to get to know your partner even better? Plan a cheeky game of truth or dare for your next at-home date night with these truth or dare questions for couples.