140+ Fun & Deep Hypothetical Questions for Couples

Hypothetical questions are a fun way to get to know your partner better and build a deeper connection. These types of questions are great for starting interesting conversations because they get your partner’s imagination going with creative “what if” scenarios. They’re also a chill way to give you insight into your partner’s fears, desires, and values. Plus, we spoke with dating coaches to find out their best tips for asking your partner questions to deepen your bond. Read on to find out what they said!

The Best Hypothetical Questions for Couples

If we could relive one day of our relationship, which day would you choose?
If you were a ghost who was stuck in one building, what would it be?
If you could go back to one day in your childhood, which would it be?
If there was a movie made about us, what would be the major plot twist?
If you could choose one career path for me, what would it be?

Section 1 of 14:

Flirty Hypothetical Questions for Couples

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Put the spark in your relationship with these flirty questions. Professional matchmaker and dating coach Lauren Sanders suggests asking your partner about their romantic preferences to build intimacy.^{[1]
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Expert Source

Lauren Sanders
Matchmaker & Dating Coach

Expert Interview} Talking about love and romance helps create a flirty spark between you. It can also help you understand what they want in a relationship. Try one of these to get started:
- If you had to describe the feeling of falling in love in one sentence, what would you say?
- Suppose we had a chance to kiss anywhere in the world. Where would it be?
- Imagine we’re going out on the perfect date night. Would it be casual or fancy?
- If you could make the perfect partner, what personality traits would you pick?
- If a genie offered to create the ideal relationship, would it be monogamous, polyamorous, or open?
- How connected are emotional intimacy and physical intimacy for you? Do you need to have one to enjoy the other?
- If you could only have one type of kiss for the rest of your life, which would you want it to be?
- Imagine seeing the perfect person. What physical qualities would they have?
- If we just met, how long would it take you to realize there was chemistry between us?
- Do you think it’s better to have a specific “type” or be attracted to lots of different types of people?

Section 2 of 14:

Juicy Hypothetical Questions for Couples

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Start an engaging conversation with these juicy questions. If you’re not in the mood for an intense discussion, try some fun, lighthearted hypotheticals to pass the time or spend quality time together. Plus, you can learn more about their personality, interests, and beliefs without getting too heavy.^{[2]
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Research source} Ask one of these to start a lighthearted conversation:
- If we could relive one day of our relationship, which day would you choose and why?
- What would I hear if I asked a group of people who know you for five adjectives to describe you?
- Which place on the planet would you never want to live, and why?
- Would you rather forget about yourself or forget about anyone else?
- Which mask would you like if you had to wear one for the rest of your life?
- What music would you prefer if you could just listen to one song for the rest of your life?
- What show would you like if you had to be trapped in a TV show for a month? And who would you be if you were a character?
- How would you handle a situation at work where you were asked to execute a task that went against your morals?
- If you were a ghost who was stuck in one building, what would it be?
- If you could go back in time and live in any historical era, which would you pick?

Section 3 of 14:

Spicy Hypothetical Questions for Couples

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Turn up the heat with these spicy hypothetical questions. Get your partner hot and bothered while you learn more about them by shifting your questions from flirty to dirty! Use these questions as an opportunity to discover his sexual preferences and desires. You can improve your sex life and become irresistible in the bedroom.^{[3]
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Trustworthy Source

Harvard Medical School
Harvard Medical School's Educational Site for the Public

Go to source} Ask your partner the following questions to turn them on and build sexual tension:
- Would you rather have your parents walk in on you having sex in their bed OR show your parents your entire porn search history?
- Would you rather send nudes to your boss or your parents?
- If you could try any new type of foreplay in the bedroom, what would it be?
- Would you rather be able to have sex, but only if a tarantula is crawling on you, OR never have sex again?
- Would you rather never have sex again OR never eat your favorite food again?
- Would you rather never wear underwear again or never wear socks again?
- Would you rather wear the same thong for a month OR wear a stranger's dirty boxers for two weeks?
- Would you rather walk in on your parents having sex or have your parents walk in on you having sex?
- Would you rather always have sex in the dark OR always have sex with the lights on?

Section 4 of 14:

Fun Hypothetical Questions for Couples

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Throw in a few fun questions to lighten the mood. As dating coach and matchmaker Laura Bilotta explains it, “the goal of joking around with a [partner] is to build a connection and create a fun, lighthearted atmosphere.”^{[4]
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Expert Source

Laura Bilotta
Dating Coach & Matchmaker

Expert Interview} Goofy questions are a great way to lighten the mood when your partner is having a bad day. Try one of these hypothetical questions to make them laugh.
- If we were to compete on a TV game show together, which show would you choose and why?
- If we were stuck on a deserted island, what three completely useless items would you want to have with us?
- If you could switch lives with any celebrity for a day, who would it be and why?
- If we could have any animal as a pet, which one would you choose and why?
- If we had to go on a “bad” date, where would you want to go?
- If we were to create a signature dance move together, what would it be?
- If you could have any superpower, what would it be, and how would you use it?
- What are some silly or playful traditions you would like to start in our relationship?
- If we were stuck on a deserted island, what three items would you want to have with us?
- If we had a whole day to ourselves with no responsibilities, what reality show would you want to binge?

Section 5 of 14:

Deep & Thought-Provoking Hypothetical Questions

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Ask serious questions to truly connect with them on a deeper level. When you’re ready to connect with your partner on a deeper level, it’s time to move from lighthearted or sexy questions to something more serious. Ask him one of these more thought-provoking questions to get a really deep conversation going.
- If you could go back in time and live in any historical era, which would you pick?
- If you could go back to one day in your childhood, which would it be?
- Would you rather lose your most cherished memory or know that you’d already had your happiest moment in life?
- Would you rather only be able to cry in front of other people or only be able to cry alone?
- Would you rather eat out for every meal or have to cook every meal?
- What would you do if you could go back in time and learn something sooner, and how would it change things?
- Would you rather have a job you love with a low lifetime earning potential or a job you hate but pays a lot?
- Would you rather know how you're going to die or know how I'm going to die?
- Would you rather have no emotions or be able to deeply feel every little thing?
- You are offered a pill that increases your intelligence by 50% but also permanently removes your hair, including your brows. Do you dare to take it?
- Would you rather change jobs every few years or keep one job for the rest of your life?
EXPERT TIP

Courtney Quinlan
Matchmaker & Dating Coach
Courtney Quinlan is a Matchmaker and Dating Coach and the Owner of Midwest Matchmaking. With over 15 years of experience, she specializes in finding individuals a compatible partner, providing guidance throughout the dating process, and crafting events for singles in the Midwest. Courtney holds a BS in Broadcast Journalism from The University of Nebraska at Omaha.

Courtney Quinlan
Matchmaker & Dating Coach

Communication is the key to any good relationship. Sometimes, it’s just being able to have open, honest communication about where you stand and where you see things in the future. That way, you can work together to make those dreams come true.

Section 6 of 14:

Hypothetical Questions about Relationships & Communication

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Learn their approach to relationships with these questions. Ask interesting questions to open conversations about your relationship and communication styles. These questions can help you get closer to each other while communicating what you both want in a relationship.^{[5]
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Research source} Try one of these to help better communicate your needs in a fun way.
- What’s one piece of advice you would give your younger self about communication?
- If there was a movie made about us, what would be the major plot twist?
- Suppose we started a podcast together; what would be our first topic?
- How would our relationship change if we always knew the perfect thing to say to each other?
- If we had to switch roles for a day, what do you think would be the biggest challenge?
- If there was one fight we’ve had that you could completely understand from my perspective, what would it be?
- If we could only use emojis to communicate for a week, which five emojis would you use the most?
- If we had a crystal ball that could tell us our future, would you look?
- If there was a relationship guide written just for us, what would the title be?
- If you could instantly gain one skill or talent to impress me, what would it be?

Section 7 of 14:

Hypothetical Questions about Future & Goals

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Ask about their goals to see where your relationship is headed. Make an effort to learn more about your partner’s goals for the future of your relationship. Asking questions about marriage and family helps ensure your vision for the future lines up. It can also help you determine your compatibility in the long run.^{[6]
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Research source} Ask one of these to get the discussion rolling:
- If we had unlimited resources, what philanthropic activities or causes would you want us to support?
- If we could start a business together, what type of business would you want it to be?
- Imagine if one day we woke up with a new ability to help people; what do you hope it would be?
- Suppose you could ask a single question about our future and get an honest answer, what would it be?
- If money were no object, what would be your dream vacation and why?
- If we could implement one major change in society to better our future, what would it be?
- If you could choose one career path for me, what would it be?
- What are some shared goals or dreams you would like us to pursue together?

Section 8 of 14:

Hypothetical Questions about Romance & Intimacy

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Show them your romantic side with thoughtful questions about intimacy. Ask your partner questions that delve into their thoughts about romance to build intimacy in your relationship. These types of questions help you understand your partner’s feelings about your relationship and what they need to feel loved.^{[7]
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Research source} Here are some meaningful questions to get you started:
- Suppose every time we hugged, we could feel what the other person was feeling; what do you think I’d learn about you?
- What song would you choose as our theme song if our relationship were a movie?
- If we could go back to the beginning of our relationship, what would you do differently in terms of romance?
- If we could relive one date from our past, which would it be and why?
- If you could plan the perfect day for us, what would it include?
- Imagine we’re stranded on a deserted island; how would we spend our days?
- Suppose we had a chance to kiss anywhere in the world. Where would it be?

Section 9 of 14:

Hypothetical Questions about Trust & Loyalty

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Pose a hypothetical to start a conversation about trust and loyalty. Loyalty is one of the most important elements of a solid long-term relationship.^{[8]
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Research source} This is especially true during difficult times. Use these questions to gain a better understanding of what loyalty in a relationship means to them so you can learn how to be better, more supportive partners to each other.
- What’s one act of loyalty you’d want from me in difficult times?
- If we had to prove our trust to each other without words, how would you do it?
- If you could guarantee one aspect of our relationship would never change, what would it be?
- If you could ask one question about my past and get an honest answer, what would it be?
- If you had to choose one person to be completely honest with you at all times, who would it be?
- Imagine trust is a color that glows around people. What color do you think would be around me?
- What’s the most important promise you think we should make to each other today?
- If there was a test that could measure our loyalty to each other, would you want us to take it?
- If you could put a truth spell on me, would you?

Section 10 of 14:

Hypothetical Questions about Values & Beliefs

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Delve deeper into their beliefs with questions about what they value. Build emotional intimacy with your partner by asking them questions that explore the values and ideas that factor into their worldview.^{[9]
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Research source} Ask him questions that dive into his political convictions, religious beliefs, and thoughts about social issues.
- Suppose our relationship had a motto based on our beliefs; what would it be?
- What’s one belief you hold that you think everyone in the world should adopt?
- If you could change one societal norm about relationships, what would it be?
- If you could instill one hope in the hearts of everyone we meet, what would it be?
- If we could both fully adopt one value from each other, what value would you want from me?
- How would our relationship change if we shared the exact same beliefs?
- If there was one historical figure you could bring back to discuss their beliefs with us, who would it be?
- Imagine if we could teach one core value to a classroom of kids; which value would we teach?
- If you could see the impact of one of your beliefs 100 years in the future, which belief would you choose?
- Suppose we had to argue a major moral issue in a debate; which side would you take?

Section 11 of 14:

Hypothetical Questions about Personal Growth & Support

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Use hypotheticals to discover how you can grow together. Matchmaker and dating coach Courtney Quinlan recommends asking them about their personal life goals.^{[10]
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Expert Source

Courtney Quinlan
Matchmaker & Dating Coach

Expert Interview} That way, you understand what they’re working toward, so you can support them in a way that’s sensitive and supports their ambitions.
- What’s one challenge you’d like us to overcome together?
- If there were a life coach for every relationship, what’s the first thing you’d ask ours?
- Suppose we both had to pick up a new hobby; what hobby would you choose for us?
- Suppose we could grant each other one personal wish; what would yours be?
- If you could pick one goal for me to achieve this year, what would it be?
- If you could choose one way for us to spend more quality time, what would it be?
- If you could have me master one skill to better support you, what would it be?
- If we could take a year off to pursue personal goals, what would you want to accomplish?
- If you could give me the gift of endless knowledge in one subject, what subject would you choose?
- If we could each drop one bad habit, what would you want us to give up?

Section 12 of 14:

The 36 Relationship Questions

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Deepen your bond with 36 questions backed by research. Social psychology researcher Arthur Aron of the Interpersonal Relationships Lab at Stony Brook University developed a series of questions that were bound to create more connection and closeness between two people. The questions were designed to give someone the impression the person asking them was interested in them.^{[11]
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Research source}
- Given the choice of anyone in the world, who would you want as a dinner guest?
- Would you like to be famous? In what way?
- Before making a phone call, do you ever rehearse what you're going to say? Why?
- What would constitute a perfect day for you?
- When did you last sing to yourself? To someone else?
- If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you choose?
- Do you have a secret hunch about how you will die?
- Name three things you and your partner appear to have in common.
- For what in your life do you feel most grateful?
- If you could change anything about the way you were raised, what would it be?
- Take four minutes and tell your partner your life story in as much detail as possible.
- If you could wake up tomorrow having gained one quality or ability, what would it be?
- If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?
- Is there something that you've dreamt of doing for a long time? Why haven't you done it?
- What is the greatest accomplishment of your life?
- What do you value most in a friendship?
- What is your most treasured memory?
- What is your most terrible memory?
- If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
- What does friendship mean to you?
- What roles do love and affection play in your life?
- Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.
- How close and warm is your family? Do you feel your childhood was happier than most other people's?
- How do you feel about your relationship with your mother?
- Make three true "we" statements each. For instance, "We are both in this room feeling..."
- Complete this sentence: "I wish I had someone with whom I could share..."
- If you were going to become a close friend with your partner, please share what would be important for them to know.
- Tell your partner what you like about them. Be honest this time, saying things that you might not say to someone you've just met.
- Share with your partner an embarrassing moment in your life.
- When did you last cry in front of another person? By yourself?
- Tell your partner something that you like about them already.
- What, if anything, is too serious to be joked about?
- If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven't you told them yet?
- Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?
- Of all the people in your family, whose death would you find most disturbing? Why?
- Share a personal problem and ask your partner's advice on how they might handle it. Also, ask your partner to tell you how you seem to be feeling about the problem you have chosen.

Section 13 of 14:

Why ask hypothetical questions in relationships?

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Hypothetical questions are a tool for starting good conversations. Asking your partner these types of questions regularly shows them you’re genuinely interested in hearing and understanding what they have to say. They also help you maintain a closer relationship with more consistent communication. Posing hypotheticals also helps you avoid making assumptions about what your partner feels.^{[12]
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- Asking these questions in an established relationship helps build trust, align goals, and resolve conflicts.^{[13]
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- Try asking questions in a new relationship to gain understanding, discover common interests, and get closer to the other person.

Section 14 of 14:

How to Have Great Relationship Conversations

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Pick 4-5 questions to start so they don’t feel overwhelmed. “Narrow it down to maybe the most important four or five questions,” suggests Sanders.^{[14]
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Expert Source

Lauren Sanders
Matchmaker & Dating Coach

Expert Interview} Use the questions to get an interesting conversation started without making them feel like they’re being interrogated.
- When you ask a question, try to come from a place of genuine interest.
- Don’t just throw out a question and move on right away. Share your thoughts about their answer and have a real conversation.^{[15]
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Use good active listening skills when they answer. Active listening shows you’re genuinely interested and paying attention to your partner’s answers. Focusing on the other person and what they’re saying is key to having a good conversation.^{[16]
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Greater Good in Action
An initiative by UC Berkeley's Greater Good Science Center promoting science-based practices for a meaningful life

Go to source} Here are some important active listening tips to follow:
- Use engaged body language by facing the other person, making eye contact, nodding, and reacting to what they say with appropriate facial expressions.
- When they finish talking, summarize what they say back to them or ask for clarification to show you were listening.
- Take the conversation deeper by asking thoughtful follow-up questions to show you’re interested in learning more about them.
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Keep track of their answers to make plans for the future. Quinlan suggests using what you learn in your conversations to plan fun future dates and activities with them.^{[17]
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Expert Source

Courtney Quinlan
Matchmaker & Dating Coach

Expert Interview} This is a great way to ensure your significant other enjoys the activities you plan. It also shows them you paid attention to what they said and care about their perspective.
- For example, if they tell you how much they loved riding roller coasters when they were a kid, consider surprising them with a trip to an amusement park.
- If you learn they enjoy reading in their free time, invite them to a silent book club meeting for a date night.

Join the Discussion...

What are some fun questions to ask your partner?

April Davis
Matchmaker

Here are some of my favorite questions to ask your partner to strengthen your connection:

What fictional character was your hero growing up?
What food could you eat every day and not get tired of?
What's your favorite memory from any vacation you've been on?
What's your dream date idea?
What songs remind you of me?
What's the wildest thing on your bucket list?
If you could live anywhere in the world, where would you be?
If you could invent a holiday, what would it be?