When’s the last time you had a meaningful conversation? Or deepened your relationship with someone in your life? Knowing how to have a deep conversation isn’t easy. That said, diving into deep topics—whether with a romantic partner or a friend—is crucial to maintaining an intimate connection. 

In an experiment, social psychologist Arthur Aron found that pairs who discussed ‘deep questions’ were much more likely to maintain their level of connection than those who kept to small talk.

52 Questions For Deeper Conversations - Lemonade Blog

Since relationships are undoubtedly one of the most important aspects of our lives, Lemonade decided to examine several psychological studies, and figure out which conversation topics foster closeness.

From there, we created a list of 52 questions that can scientifically foster intimacy between you and your partner, roommate, or friend—one for every week of the year!

Ritualize deep conversation

Looking for deep things to talk about with your significant other? You’re in luck.

We suggest creating a weekly ritual of asking these questions – try it on a Friday night to recap the week. You can spiral off into other topics, but the point is to start a real conversation, and learn more about your partner.

And don’t forget to ask: Are all the things I care about covered by Lemonade?


So bookmark this page, grab your partner or friend, and start reclaiming conversation!

52 questions to foster (or maintain) closeness and intimacy

1. What do you miss about being a kid?

2. If someone gave you enough money to start a business – no strings attached – what kind of business would you want to start and why?

3. Tell me about a relationship issue you’re having, and ask me for advice on how to fix it.

4. If you could go back in time, what’s one piece of advice you’d give to your younger self?

5. What’s something you want to do in the next year that you’ve never done before?

6. Tell me three things that happened in the last week that you’re thankful for.

7. What’s your favorite memory we’ve shared together? Gimme as many details as possible.

8. What makes you happy?

9. Who or what has changed your life?

10. How do you best connect with others?

11. Are you a giver, a taker, or a matcher? Are there areas in your life where you act like one type, and other areas where you act like another? [Here’s the Giver/Taker Test]

12. What are the five most important things on your bucket list?

13. What matters most to you?

Here’s a question: Did you know Lemonade offers insurance for your stuff, your pet, and your car?


14. What’s some of the best advice you’ve ever gotten?

15. What’s your ideal weekend?

16. If you could take a year-long paid sabbatical, what would you do?

17. Who do you trust?

18. What are five things you’re thankful for right now?

19. If a genie granted you three wishes right now, what would you wish for?

20. What’s the craziest thing you’ve ever done and would you do it again?

21. What’s your favorite family tradition?

22. If you could enter a time machine, what time period would you go to?

23. What’s your favorite quote?

24. What do you value most in a friendship?

25. Tell me your life story in four minutes, with as many deets as possible.

26. What’s something I’ve done for you that you’re grateful for?

27. What do you want your legacy to be?

28. Let’s alternate sharing three positive characteristics of each other.

29. What are your biggest goals for this year? How will you work to achieve them?

30. Where was your favorite place to go as a child and why did you love it there?

31. Tell me about a challenge you’ve been having at work or school, and ask me for advice on what to do about it.

32. What was the first thing you bought with your own money?

Ask yourself—do you have coverage for the things that matter to you?


33. What are you curious about?

34. What are your top three strengths? Which strengths do you look for in a friend or partner? [Take the VIA Strengths Test]

35. Name four things we have in common.

36. What are your favorite three topics to talk about?

37. What’s your earliest memory?

38. How do you express gratitude towards others? Give me an example.

39. What are the top three ways to express your love in friendships and in relationships? (Here’s the Love Languages Quiz)

40. In what situations do you feel most comfortable sharing your perspective?

41. Who’s someone you really admire?

42. How do you like to be comforted when you’re upset?

43. What would you do on your “perfect” day?

44. In 10 years, how would you like to describe your life?

45. If you had $100,000 to give away to any cause, which cause would you choose and why?

46. Where are the top three places you want to travel to some day, and why?

47. If you could have any job you wanted, that would it be?

48. Tell me about a day you had that you’ll never forget.

49. If there were 26 hours in a day, what would you do more of?

50. Is there something you’ve dreamed of doing for a long time? Why haven’t you done it yet?

51. What moments or events during your childhood shaped who you are now?

52. What do you think about most?

The methodology behind these questions

These questions will help you and your loved one dive into deep and meaningful topics that are proven to enhance intimacy. But which topics are scientifically proven to bring you closer to another person?

Here’s a look at 6 central ideas behind our 52 questions, and why these topics bring us closer together:

According to psychologist Robert Emmons, gratitude is good for our bodies, minds, and relationships. Whether you discuss what you’re thankful for, or express appreciation for your partner’s good deeds, gratitude deepens our relationship with others. Why? Gratitude does a few things: it establishes trust and intimacy, creates higher relationship satisfaction, and encourages you and your loved one to give even more.

Here’s how it works: when you do something your partner is grateful for, it creates norm of reciprocity, and inspires your partner to do something nice in return. With this chain reaction, you and your loved one will feel even more gratitude towards each other, which will make your relationship even stronger.

Speaking of gratitude, reminiscing on past events is a sure way to inspire feelings of appreciation. A study by psychologist Clay Routledge found that recounting shared moments between you and your loved one increases feelings of social connectedness, and even makes you more supportive and considerate of each other.

To dig even deeper into nostalgia, we suggest talking about your experiences growing up.

“Discussing each other’s childhoods can really build an intimate bond between partners. Expressing how you felt as a child and things that hurt you when you were young gives your partner real insight into what shaped you as an adult,” said relationship guru Rob Alex.

“That understanding of how you felt in good times and bad times as a kid really allows your partner to see your vulnerabilities, and can evoke deep feelings and connections with each other.”

Giving (and asking for) advice
Giving advice is one of the most powerful forms of engagement between two people, according to Professor Julia Glazer. When you advise a loved one on a challenge they’re facing, it signifies that you’re willing to be honest to them, and that you care about them. Combined, these two signals communicate an extremely high level of trust, which creates a deeper level of closeness (and trust us, trust pays off). (Psychology Today)

On the other side of it, asking for advice and expressing vulnerability also fosters intimacy. “One key pattern associated with the development of a close relationship is sustained, escalating, reciprocal, personal self-disclosure,” wrote Psychologist Arthur Aron in his study An Experimental Generation of Interpersonal Closeness.

When you share something with your partner – whether it’s a deep secret, a dream, or an aspiration – something crazy happens in your brain. Your pleasure centers light up like a Christmas tree, and a hormone called oxytocin is released. Another name for oxytocin? The ‘love hormone,’ because it plays a huge role in forming bonds between two people.

Several new studies show that the release of oxytocin makes us more sympathetic, supportive, and open with our feelings. In fact, research conducted by couple therapist Beate Ditzen found that oxytocin release helps loved ones manage conflict more effectively; when it’s released, women show a decrease in a social stress hormone, whereas men become better at communication, make more eye-contact, and become more open about their feelings – all essential behaviors for resolving conflict peacefully.

Learning each other’s preferences
If we know what our loved ones like and dislike, we’ll better understand how to be a good companion for them. This may seem obvious, yet many of us neglect to ask our partners about their preferences point blank. By asking which activities they enjoy most, where or how they want to live, and what they value in their friendships with others, understanding their perspective will help us become better partners.

Similarly, learning how your loved one likes to be comforted when times are tough is a valuable conversation to have. “The one conversation couples can have in order to build intimacy is to ask: How can I help you when you’re suffering? Or, how would you like me to react when you’re in pain?” says clinical hypnotherapist Rachel Astharte.

It’s no coincidence that dating sites link people based on what they have in common – social science tells us that commonalities keep relationship strong.

According to psychologist Donn Byrne, we feel more connected to people who hold similar attitudes as us. In fact, a review of 313 studies with over 35,000 participants found that similarity is a very strong predictor of attraction and connection in relationships. Why? Because when two people have a similar gravitational pull, it creates less division and less judgement among them.

Discovering what you and your loved one have in common – whether it’s an opinion, a habit, or a favorite food – will bring you closer together and remind you of your friendship. Plus, reflecting on your common experiences will elicit gratitude (bringin’ it back!) for the relationship you have and the memories you share.

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Thanks for reading! For more science-backed life hacks, check out the Lemonade Blog. To take Lemonade renter’s insurance or homeowners insurance for a spin, check our prices in 90 seconds.

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