85 Deep Conversation Starters to Strengthen Your Relationship

No matter how long you and your partner have been together—for three months or thirty years—a meaningful discussion never loses its importance. When you talk about light subjects with favorite movies and take serious questions about future life and the most significant fears, you learn what is essential for another person. A relationship that’s more emotional and safer: the more you get used to discussing, the more comfortable these topics turn.

“Your conversation skills are just like other disciplines,” says relationship therapist Lila Morgan. “When you discuss topics in your existing comfort zone, the better you become ready for deep conversations and emotionally risky questions.”

While many studies focus on the way the right couples communicate, the meaning of such conversation is more substantial. “If both of the partners invest time to connect each other to see each other meaningfully, it builds the basis for challenges later on.” Morgan says. “Especially if they started to think about long-term serious connections.”

However, a deep chat should not be something heavy. Below, you can see expert opinion from Lila Morgan on how you can start these essential topics more easily and learn the list of 85 conversation starters that will help you both feel even closer.

How to Make Deep Conversations Feel Less Intimidating

Make it fun: Although questions might be crucial, their statement should not be something super stiff. You can use flashcard games, or even prompts online can translate these talks into funny games. “You start the conversation with pre-set prompts, so you both feel like you’re having a game,” Morgan says. “That means that partner’s questions are not something too focused or sneaky”,

Another easy entry point? Pop culture. “Books, shows, or movies you have watched together can be low-key ways to have discussions about values,” she says. “Rather than talking about yourselves directly, you are exploring fictional characters and their choices — which still tells you a lot about your own values,” she said.

Ready to start? And if you need more inspiration for your next one-on-one, here are 85 insightful questions, organized by category.

Underneath type of conversation starters about family

• Which family member are you most honest with?
• What is your most unusual or special family tradition?
• What is your family’s way of saying “I love you”?
• Do you want to be a parent? Why or why not?
• What do you wish you could change about your upbringing?
• Do you anticipate taking care of your parents when they’re old?

Deep Topics For Discussion About Childhood

• Which childhood hobby do you miss and why?
• What was the most influential book you read as a child?
• What is the food you most associate with home?
• What family rules, if any, would you pass along?
• Should kids be made to do chores?
• Which teacher had the biggest impact on your life?
• How have you changed since high school?
• Who was your favorite cartoon character when you were a child?

Deep Romantic Conversation Starters for Him or Her

• What’s your love language?
• Tell me about your early heart breaks.
• Do you believe in soul mates or twin flames?
• When did you first tell someone, outside of your family, “I love you”?
• What is your definition of being good in bed?
• What’s a simple thing you find attractive for no apparent reason?
• What about physical touch indicates love to you?

Deep Relationship Conversation Starters

• What’s your favorite memory we share?
• What’s something you want to ask me but are too scared?
• Name three things we have in common.
• What’s one thing you would change in our relationship?

Deep Conversation Starters on the Past

• What have been the best and worst moments in your life?
• Whom would you apologize to from your past, and why?
• What is your proudest accomplishment to date?
• What’s the biggest mistake you’ve made, and what did you learn from it?
• Have you had a significant health scare?
• Tell us about a time when you got thrown into a situation outside of your comfort zone.
• What’s the greatest risk you’ve ever taken? Would you do it again?
• Is there someone you’ve lost touch with whom you’d like to reconnect?

Engaging Questions on the Future

• One question to ask a psychic?
• What does the home of your fantasies look like?
• Where will you be in 5 years?
• What’s the single most important goal you want to achieve over the next decade?
• Where in the world would you most like to live?

Deep Conversation Starters About Money 

• What do you spend a lot of money on that you wish you didn’t?
• Are you a spender or a saver?
• Should couples have joint financial accounts?
• Would you borrow money for something you want badly, or would you wait?
• What is something that is always worth splurging on?
• What’s not worth the money?
• What Is Your Biggest Financial Regret?
• Do you want to own your dream home or travel the world?

Deep Conversation Starters Around Personal Preferences

• What is your ideal day on your own?
• What’s your favorite solo thing to do?
• What’s your greatest source of stress while traveling?
• What are your go-to self-care practices?
• Do you like to work out? If so, how?
• What is one thing that always makes you happy at a low point in your life?
• How do you feel about recreational drug use?
• When are you at your most powerful?
• Is it ever okay to lie?
• What movie have you watched the most?
• What bizarre topic catches your interest?
• Would you ever get a tattoo?
• What do you not understand the hype about?
• What quotation would you want to hang on your wall?

Deep Conversation Starters About Work and Career

• If you could be a celebrity or wealthy, which would you choose?
• What motivates you at work?
• If your job didn’t earn money, what would you be doing?
• Where do you picture your career in a decade?
• Who are the people you most admire at work?

Deep Conversation Starters f Deep Conversation Starters on Charity and Giving

• If you had $1 million to give to a charity, which would it be?
• What is the most recent kind thing you did for a stranger?
• Have you ever made a donation in the name of someone you didn’t know?
• Which would you prefer to donate to a cause you care about — time or money?

Philosophical Deep Questions to Start a Conversation

• How would you spend your time if there was only a year left to live?
• How would you react if I or you were told we were going to die, and there was nothing we could do about it?
• What is more valuable, understanding or forgiveness?
• Know something exists outside this world?
• What’s one article or story from the last year that you think everyone should read?
• If you had to give up one of your senses, which would it be and why?

Deep Questions About Life: Self-Reflective Discussion Starters

• What comes naturally to you?
• What would you like others to appreciate more about you?
• What are you most thankful for?
• What are you most selfish about?
• How would other people describe you in three words?
• What worries you most?
• What do you wish you were more skilled at?
• When’s the last time you worked really hard at something that was not for work or school?
• Who is a non-famous person you really admire?
• If someone were to play you in a movie, who should it be?