100 Would You Rather Questions for Boyfriend

If you have already discussed questions such as “What is your favorite movie?” and “Where do you see yourself in five years?”, then it’s time to move on to the most interesting part of the conversation — questions like “What would you choose?” These questions make him think deeply and reveal sides of his personality that you haven’t seen yet.

Questions like “What would you choose?” are essentially gold for conversation. They are divided into three carefully thought-out categories:

LIGHTHEARTED: playful, fun, easy to answer
REVEALING: thought-provoking, value-based, insightful
INTIMATE: personal, vulnerable, deeply connecting

However, there’s something crucial to understand before you start: the way you present these questions shapes the entire experience.

Making Would You Rather Questions Feel Natural (Not Like Homework)

The point of these questions isn’t to conduct research — it’s to build closeness. You’re not evaluating him; you’re creating space for both of you to explore ideas and learn about each other organically.

Ease Into It Gradually

Open with fun, simple scenarios before transitioning to weightier topics. Great conversations spark from humor and comfort, not from jumping straight into serious territory (though that can emerge on its own).

For instance: “Would you rather never have to do laundry again or never have to wash dishes?”

That’s easy and relatable. “Would you rather lose your job or have me lose mine?” — save that for when trust is deeper.

Focus on Understanding His Thought Process

His reasoning matters more than the choice itself. Asking “What made you pick that one?” demonstrates real curiosity. The meaningful part isn’t the answer—it’s discovering how his mind works through decisions.

Keep the Energy Equal

This works best as a true dialogue, not an interrogation session. Trade questions back and forth. After he responds, offer your own thoughts—whether you agree, see it differently, or have a surprising take. The magic happens in this give-and-take.

Pick the Right Setting

Avoid times when either of you feels rushed or distracted. These questions thrive during cozy nights in, scenic drives, or late-night conversations when you’re both relaxed and present.

Honor His Comfort Level

Pushing past obvious discomfort will kill the mood instantly. When a question doesn’t land well, simply move on without making it awkward. The aim is connection through willing participation — never through pressure.

With the right environment established, everything else falls into place effortlessly. Excited to go deeper? Let’s turn ordinary chit-chat into conversations you’ll both remember.

The Easy Category — Light, Entertaining & Character-Building

Consider these your conversation starters. These fun questions create comfort, generate laughs, and give your boyfriend room to express himself naturally without any stakes.

Everyday Preferences

1. Would you rather always be 10 minutes late or always be 20 minutes early?
2. Would you rather have unlimited coffee or unlimited pizza for life?
3. Would you rather lose your phone for a month or your wallet for a week?
4. Would you rather have a rewind button or a pause button for your life?
5. Would you rather always be slightly cold or slightly warm?
6. Would you rather never have to sleep or never have to eat?
7. Would you rather communicate only through emojis or only through rhymes?
8. Would you rather have breakfast for every meal or dinner for every meal?
9. Would you rather give up social media or streaming services?
10. Would you rather be able to speak every language or play every instrument?

Adventure & Experiences

1. Would you rather travel to the past or the future?
2. Would you rather explore space or explore the ocean depths?
3. Would you rather live in the mountains or by the beach?
4. Would you rather have free flights for life or free hotels for life?
5. Would you rather experience all four seasons or endless summer?
6. Would you rather go on a safari or visit ancient ruins?
7. Would you rather road trip across the country or backpack through Europe?
8. Would you rather camp under the stars or stay in a luxury resort?
9. Would you rather swim with dolphins or hike to see the Northern Lights?
10. Would you rather visit every US state or every European country?

Superpowers & Fantasy

1. Would you rather be able to fly or be invisible?
2. Would you rather read minds or see the future?
3. Would you rather have super strength or super speed?
4. Would you rather control fire or control water?
5. Would you rather talk to animals or speak all human languages?
6. Would you rather time travel or teleport?
7. Would you rather never age or have unlimited wealth?
8. Would you rather be the funniest person or the smartest person in any room?
9. Would you rather have a dragon or be a dragon?
10. Would you rather live in a world without music or without movies?

Lighthearted questions are your foundation — enjoyable, revealing, and full of personality.

The Revealing Level — Thought-Provoking, Value-Based & Insightful

Now we’re in territory where a question isn’t just entertainment anymore — it’s a window into who he really is. The Revealing level is where preferences become priorities, and his choices tell you what matters most.

Values & Character

1. Would you rather be respected or be liked?
2. Would you rather have a job you love with low pay or a job you tolerate with high pay?
3. Would you rather be famous for something you’re proud of or wealthy from something meaningless?
4. Would you rather give up your biggest dream or watch someone you love give up theirs?
5. Would you rather know when you’ll die or how you’ll die?
6. Would you rather have true love or financial security for life?
7. Would you rather be known for your intelligence or your kindness?
8. Would you rather change one thing about your past or know one thing about your future?
9. Would you rather lose all your memories or never be able to make new ones?
10. Would you rather forgive easily or never forget?

Relationships & Priorities

1. Would you rather have few deep friendships or many casual friendships?
2. Would you rather your partner be brutally honest or tactfully gentle?
3. Would you rather have more time or more money?
4. Would you rather be alone and at peace or surrounded by people but stressed?
5. Would you rather have family nearby or complete independence far away?
6. Would you rather your partner challenge you or comfort you?
7. Would you rather support someone else’s dream or pursue your own?
8. Would you rather be with someone who shares all your interests or complements your differences?
9. Would you rather have constant communication or quality conversation?
10. Would you rather be understood by few or admired by many?

Life Philosophy

1. Would you rather live a short, exciting life or a long, peaceful one?
2. Would you rather have answers to all your questions or questions that keep you curious?
3. Would you rather make a big impact for a few or a small impact for many?
4. Would you rather be remembered for 100 years or forgotten but have helped more people?
5. Would you rather take a guaranteed safe path or risk everything for your dreams?
6. Would you rather have no regrets but no great stories or regrets with amazing memories?
7. Would you rather know all the mysteries of the universe or master one meaningful skill?
8. Would you rather live without pain or live without fear?
9. Would you rather have a life of comfort or a life of purpose?
10. Would you rather be an optimist who’s sometimes disappointed or a realist who’s never surprised?

Revealing questions are where you stop guessing and start truly knowing him.

The Intimate Level — Personal, Vulnerable & Deeply Connecting

Okay, this is the meaningful territory. The Intimate round is for couples who trust each other, want real connection, and are ready to be genuinely open — together.

Relationship Depth

1. Would you rather I always tell you the hard truth or protect your feelings sometimes?
2. Would you rather spend every weekend together or maintain some independence?
3. Would you rather we never argue or work through disagreements together?
4. Would you rather I support all your decisions or challenge you when I disagree?
5. Would you rather be needed by me or wanted by me?
6. Would you rather we communicate constantly or give each other space?
7. Would you rather I be your best friend or your passionate partner?
8. Would you rather share everything or maintain some mystery?
9. Would you rather grow together in the same direction or grow individually?
10. Would you rather I show love through words or actions?

Vulnerability & Fears

1. Would you rather share your biggest fear with me or keep it private?
2. Would you rather be loved for who you are or admired for who you could become?
3. Would you rather fail publicly at something important or never try at all?
4. Would you rather I see you at your weakest or only when you’re strong?
5. Would you rather open up slowly over time or share everything immediately?
6. Would you rather be alone when you’re struggling or have me there even if you push me away?
7. Would you rather overcome your biggest insecurity or accept it completely?
8. Would you rather be vulnerable and risk getting hurt or guarded and miss deep connection?
9. Would you rather I know your worst thoughts or never truly know you completely?
10. Would you rather process emotions alone or together?

Future & Dreams

1. Would you rather live in the city I want or the place you’ve always dreamed of?
2. Would you rather we prioritize career success or relationship quality?
3. Would you rather have kids or focus entirely on our partnership?
4. Would you rather build wealth together or create experiences together?
5. Would you rather I follow my dreams even if it’s hard on us or sacrifice for stability?
6. Would you rather face challenges together or protect each other from hardship?
7. Would you rather know we’ll definitely make it or take it day by day?
8. Would you rather we plan everything or figure it out as we go?
9. Would you rather I become everything you hoped or surprise you by being different?
10. Would you rather our future be predictable and secure or uncertain but exciting?

Bonus 10 — Relationship Wildcards

1. Would you rather hear what I really thought when I first met you or keep wondering?
2. Would you rather we always agree or have passionate debates?
3. Would you rather I change something about myself for you or stay exactly as I am?
4. Would you rather relive our best memory together or create an entirely new one?
5. Would you rather know my biggest secret or let me keep one thing private?
6. Would you rather we have easy love or love that makes us both better?
7. Would you rather I need you less or want you more?
8. Would you rather compromise on big things or stand firm on our values?
9. Would you rather we be best friends who fell in love or lovers who became best friends?
10. Would you rather hear what I love most about you or what I hope never changes?

Closing Thoughts — Simple Games, Profound Bonds

Would you rather questions serve a purpose beyond just passing time — they’re tools for genuine connection. They transform casual chats into opportunities for deeper understanding and strengthen the emotional threads between you.

No matter if you’ve been together for years or are still learning each other’s rhythms, the right questions prove that there’s always something new to uncover about the person beside you.

When everyday conversation starts feeling like autopilot, break the pattern. Choose a question that matters — and pay attention to where it leads you both.