85 Deep Conversation Starters for Couples

Whether you and your partner have been together for three months, three years, or three decades, your relationship can still benefit from enriching conversation. From discussing seemingly trivial topics (favorite movies, dream vacation spots) to diving in on the most important ones (greatest ambitions, biggest fears), any conversation that helps you find out more about what your significant other wants out of life is a worthwhile one. The more you chat, the more at ease you’ll feel with one another—which is crucial when it comes to opening up about sensitive subjects.

“Communication skills are just like any other skill,” says relationship therapist Esther Boykin. “The more you practice, the better you are at it—particularly when it comes to conversations where you feel vulnerable.”

While plenty of research has been devoted to healthy communication strategies for couples, the content of your conversations is just as important. “When couples can focus on not just how to communicate, but what they communicate to each other, it can make those tougher conversations down the road, as you’re thinking about getting married, a lot easier,” adds Boykin. 

While it sounds like a lot of hard work, it doesn’t have to be. Read on for Boykin’s tips for making meaningful conversations feel less high-stakes, as well as a list of deep conversation starters for couples that are sure to encourage bonding at a level you’ve never experienced before.

How to Make Deep Conversation Less Intimidating 

First things first: Try to make these conversations fun! Yes, you’re potentially scratching the surface on deep, important topics, but that doesn’t mean you can’t enjoy the experience, too. From flashcard games to viral online guides, there are plenty of prompts available to inspire a deep conversation. “When you start with questions generated by someone else, it makes [the experience] feel like a game—and it reduces the likelihood that we begin to attach meaning to why our partner is asking a question,” says Boykin. 

You can also use pop culture as your jumping-off point. “Books, movies, and shows you’ve watched together are an easy, low-conflict way to have conversations about values,” Boykin adds. “Instead of [issues] becoming hyper-personal, you’re talking about a fictional character and the choices you see them making.” Discussing whether or not you agree with their decisions can be an indirect but just as truthful way of revealing what governs your own heart.

Ready to start a deep conversation with your partner? Read on for thought-provoking questions for couples to ask each other, helpfully sorted by category.

Deep Conversation Starters About Family

1. Who is the person in your family you’re the most honest with? 
2. What is your most unique family tradition? What is your favorite family tradition? 
3. How does your family express love and affection? 
4. Do you wish to be a parent? If so, why? 
5. If you could change one thing about the way you were raised, what would it be and why? 
6. Do you plan to take care of your parents in their old age?

Deep Conversation Starters About Childhood

1. What did you enjoy doing as a kid that is no longer part of your life?
2. What book had the most impact on you in childhood? 
3. What book had the most impact on you in childhood? 
4. What food or drink most evokes a feeling of home for you? 
5. What rules or practices did your household follow growing up that you would also implement in your own household? What rules or practices would you choose not to follow?
6. Should children help with household chores?
7. What class or teacher most impacted your life growing up? 
8. In what ways are you most different from the person you were in high school? 
9. Who was your favorite Disney or Pixar character growing up? 

Deep Conversation Starters About Romance

1. What is your predominant love language? 
2. Tell me about your first heartbreak. 
3. Do you believe in twin flames? 
4. When was the first time you said “I love you” to someone who isn’t a member of your family? 
5. What does it mean to be good in bed? 
6. What’s a very ordinary action that you find really attractive?
7. Describe the physical touch that best communicates “I love you.”

Deep Conversation Starters About Your Current Relationship

1. What is your favorite memory of us? 
2. What is something you want to ask me but are afraid to ask me? 
3. Name three things we have in common. 
4. If there was one thing you could change about our relationship, what would it be?

Deep Conversation Starters About the Past

1. What have been the highest and lowest points of your life? 
2. If you could apologize to one person from your past, who would it be and why? 
3. What is the greatest accomplishment of your life thus far?
4. What do you consider to be the biggest mistake you’ve ever made?
5. What have been the most serious injuries or health scares in your life? 
6. Tell me about a time you felt completely out of your comfort zone.  
7. What’s the biggest risk you’ve ever taken? Would you do it again? 
8. Tell me about someone you no longer speak to who you wish you were still friends with. 

Deep Conversation Starters About the Future

1. If you could ask a psychic one question about your future, what would you want to know? 
2. What does your dream home look like?
3. Where do you see yourself, personally, in five years?
4. What is the single most important goal you want to achieve in the next ten years?
5. If you could live anywhere in the world, where would it be?

Deep Conversation Starters About Money

1. Are you a spender or a saver?
2. Do you think couples should share financial accounts?
3. Would you rather incur debt to have something you really wanted right now or you prefer to wait and save?
4. Name something that’s always worth splurging on. 
5. Name something that’s never worth splurging on.
6. What’s your biggest financial regret?
7. Would you rather spend money to travel the world or have the house of your dreams?

Deep Conversation Starters About Personal Preferences

1. If you could plan one perfect day for yourself, what would it look like?
2. What’s your favorite thing to do by yourself? 
3. What stresses you out the most when traveling?
4. What are your favorite forms of self-care? 
5. Do you like to exercise? What’s your favorite form of exercise, if so? 
6. What’s something that cheers you up when you’re sad? 
7. How do you feel about drug use? 
8. When do you feel the strongest? 
9. In what circumstances, if any, is it okay to lie? 
10. What movie have you seen the most times? 
11. Tell me about the subject you’re most interested in that has the least in common with your daily life. 
12. Would you ever get a tattoo?
13. What’s something that most people you know like, but you don’t? 
14. If you were to frame and hang a quote on the wall you look at most, what would it say? 

Deep Conversation Starters About Work and Career Aspirations

1. Would you rather be very famous or very wealthy? 
2. What motivates you professionally?  
3. If salary wasn’t part of the equation, what job would you most want to do?
4. Where do you see yourself professionally in the next ten years?
5. Who do you most admire at your workplace?

Deep Conversation Starters About Charity and Philanthropy

1. If you had one million dollars to give to charity, what causes or organizations would you support? 
2. Tell me about the most recent act of kindness you did for a stranger. 
3. Have you ever donated to a random Kickstarter or online fundraiser for a person you did not know? Tell me about the most recent one. 
4. Would you rather donate your time or money to a cause you were passionate about?

Philosophical Deep Conversation Starters

1. If you were given one year to live, what would change about how you spend your time? 
2. What would you do if you were informed that you have a terminal illness? What would you do if you were informed that I have a terminal illness?
3. What’s more important: forgiveness or acceptance? 
4. Do you believe in a higher power or something beyond the physical world? 
5. Tell me about a recent article you’ve read that changed your mind about something. 
6. If you had to give up one of your senses, which would it be and why?

Self-Reflective Deep Conversation Starters

1. What’s something you’re really good at? 
2. What do you wish more people recognized you for? 
3. What are you most grateful for in life? 
4. What are you most selfish about? 
5. What three words do you think others most commonly use to describe you? 
6. What do you worry about the most? 
7. What’s something you wish you were better at? 
8. When is the last time you put a lot of effort into something outside of work or school? 
9. Tell me about the person you admire most that is not a celebrity. 
10. Who would play you in a movie about your life?