Recipes for Deeper Connection
Time-tested, meaningful questions for falling in love with life, deeply connecting with others, and adding magic to everyday interactions.
100+ lovingly hand-crafted questions …for falling in love with life …for connecting with others, and with yourself …and for infusing little sparks of magic and depth into everyday conversation
Below, you’ll find dozens of heartfelt questions, handwritten on sticky notes, that I’ve managed to snag at the end of each of the monthly Hygge NYC friendship-making gatherings I’ve hosted over the last 10 years. People arrive as strangers, and leave as friends, based solely on having shared their answers to questions written on these sticky notes.
I hope you enjoy these recipes for deep connection as much as my friends and I have.
Take them, share them, and make them your own.
~Steve Dean
1. What is your strangest habit?
2. What is your love language? What drew you to that language?
3. What is your self-talk like?
4. What’s something you’ve never been able to open up to your parents/family about but always wanted to?
5. What’s a community that should exist?
6. Have you ever done a thing-a-day (e.g. journal every day)? What did you choose, and if you haven’t, what would seem interesting or useful to choose?
7. What side projects are you working on?
8. What have you learned about yourself in the last year?
9. What’s the biggest risk you’ve taken?
10. What would you choose to do right now if you just graduated high school
11. What are your favorite natural highs?
12. What was your greatest victory?
13. What is the weirdest compliment (or insult) you’ve ever received?
14. Advice for a recent college grad?
15. What would you do on a sabbatical?
16. How do you show love to others?
17. Growing up, what were your top 3 aspirational professions?
18. What’s holding you back from a choice you want to make?
19. How do you define romance?
20. What’s your best ‘worst first date’ story?
21. What do you think are the best predictors of romantic compatibility?
We host these Hygge gatherings in a public food court where I encourage everyone to invite their friends, coworkers, family members, romantic partners, strangers they met on the street, and even their prospective dates. My goal for every gathering is to give everyone the opportunity to talk about things that are genuinely fun and meaningful to them, without needing any pre-defined outcomes. Conversation is the tool, and excited connection is our favorite outcome.
22. What is holding you back right now?
23. What’s something you used to be ashamed of?
24. What is the highest ROI habit you’ve developed?
25. If $100 million were placed into your bank account, what would the rest of your day look like?
26. What is one variable that lets you know someone would make a great lifelong friend?
27. What is your greatest insecurity?
28. What does your inner child want?
29. What is capturing your curiosity these days?
30. What are some things you’ve been excited about recently?
31. If you could give a large group of people one piece of advice, what would it be?
32. What is one memory you’d never want to lose?
33. What is a common misconception people have about you?
34. What is one thing you believe that no one else does?
35. What’s a friendship dealbreaker for you?
36. What’s 1 item on your life bucket list?
37. You become a bitcoin billionaire tomorrow. How does this alter your life trajectory?
38. What is that moment where you chose how you to live the rest of your life?
39. What is your most controversial opinion?
40. What’s something you could rant about for hours?
41. If someone gave you $100,000 to do any project you wanted, what would you do?
42. If your personality were food, what would it be? Why?
43. What is something you find value in now that was terrible at the time?
44. Describe what form your relationship structures usually take, and what form you’d like them to take.
45. What is a quality or personality trait you’d like to develop this year?
46. What is the kindest thing you’ve done for a stranger?
47. Are any curious themes popping up in your conversations lately?
48. Would you rather be a human with strawberry thoughts or a strawberry with human thoughts?
49. What advice would you give to your 18-year-old self?
50. What are your favorite vices?
51. What activities make you feel most yourself?
Starting in 2019, I learned a nifty little zine-crafting method from Alice Wong and began creating a 1-page zine at each Hygge gathering to highlight the most fun questions we came up with that evening. I invite the guests to write their questions in, and to add their doodles and drawings.
52. When do you enter a flow state?
53. If you could live anywhere on earth, where would you live?
54. Have you ever doubted that what you’re doing is meaningful?
55. Are you doing anything that you know is impeding your own happiness?
56. If money and experience didn’t matter, what job or field would you work in?
57. What is a skill or habit that you wish more of society developed for themselves?
58. How do you define yourself?
59. How will people get around in 10 years?
60. What % of your current income/net worth would you sacrifice to guarantee meeting the love of your life tomorrow? If your answer is over 50%, then what % of your future income/net worth would you be willing to give up to meet the love of your life tomorrow?
61. What’s your biggest fear?
62. What’s something you’ve made that you’re proud of?
63. What is an idea, opinion, or habit you have that surprises people close to you?
64. How did the place(s) you grew up in influence your life?
65. If you were to describe your life as a tree with a series of branches, what are the top 5 biggest, most consequential branches on your tree?
66. Where is your happy place?
67. You discover that you have 1 year left to live. How does this change your decisions moving forward?
68. How do you like to connect new people together?
69. What are 2–3 non-professional areas where you suspect you know way more than the average person?
70. What is the quality you seek most in a friend?
71. What would be the most fun even you could host in a public park?
72. What are 3 books that have shaped your life?
73. Who is your dream dinner guest and why? Would this person be different from your ideal person to get drunk/high with? Why?
74. What are you embarrassed to accept that you need to cut out of your life?
75. What was your most memorable embarrassing moment?
76. Have you ever ghosted someone or been ghosted?
77. What’s a food that makes you feel warm and grounded? Why?
78. What’s one social cause that should be important to young people around the world, regardless of location?
79. Is online dating still the best thing to do to meet people? What’s better?
80. What makes something feel like “home” for you? What makes a person feel like “home” for you?
81. What would you happily fail at?
82. What is one life goal of yours?
83. If you could work on any one project happening right now in the world right now, what would it be?
84. What is one non-work-related achievement you’re most proud of?
85. What are the important qualities in questions that start conversations you find interesting?
86. What situations or people consistently make you the most anxious?
87. What is something cool that you learned recently?
88. When have you trusted someone and they let you down? What happened?
89. Are there any passion projects you’re pumped about right now?
90. What does love mean to you?
91. What’s your favorite way to enter an altered state?
92. Who in your (chosen) family are you closest to, and why?
93. What defines a deeply memorable romantic or sexual experience for you?
94. What activities make you feel most like yourself?
95. What has been the biggest game-changer in your life over the past year?
96. What is preventing you from getting the support you need?
97. What are you trying to optimize for in life?
98. What value of yours do you find hard to express in your day-to-day?
99. What is the weirdest / most unique list you keep?
100. If you could call someone for a short conversation right before death, who would it be?
101. When is selfishness okay?
102. What was the last epiphany you had?
103. What is something you’re currently learning how to be good at?
104. What’s something you publicly hate about yourself? What’s something you publicly love about yourself? What’s something you secretly hate about yourself? What’s something you secretly love about yourself?
105. What would your top 3 laws of the land be if you were supreme leader?
106. What’s a topic you really want to learn about this year?
107. How do you hide yourself from others?
108. What is the biggest habit you had to let go of?
109. What was your most ridiculous, scary, or embarrassing travel experience?
110. If you had a full year off, rent/expense free, to do anything you most aspire to, what would you do?
111. Which smells give you the most comfort?
112. What feels like “home” to you?
113. What prevents you from deeply connecting with people?
114. Do you believe in being completely honest all the time? Why or why not?
115. How many days do you realistically think you have left to live? How’d you arrive at that number? [Bonus: Write it on a sticky note. Tomorrow, write your revised answer (minus at least 1). Repeat until you’ve found your life’s purpose.]
116. What motivates you? What fulfills you?
117. Toward which of these poles do you gravitate, and why: introspection/collaboration; stability/discovery.
118. What do you really need right now that seems to be eluding you?
119. What is the most undignified creature/moment you’ve ever witnessed
120. What made you happiest today / this week?
121. What is the most unexpected lesson you learned in life?
122. What is the most unexpected thing you turned out to be wrong about?
Some of these questions may seem like duplicates, or weirdly similar. I welcome this. I love it. It means that certain topics have remained on people’s minds for months or years on end. Certain questions may have been so impactful to some attendees that they came back and asked those questions during a subsequent gathering. The questions we ask ourselves are critical when it comes to building up our identities, sharing our stories, and gaining clarity on our intended future trajectories.
Have you come across any questions you truly love? Please share them with me, either here as a comment or by messaging me directly!
About the Author…
I’m Steve Dean, and for over 25 years, I’ve been a relationship nerd, obsessively trying to learn all that I can about how we find, form, and sustain relationships, whether romantic, professional, interpersonal, civic, or solo.
I like to write and podcast about dating, relationships, and how to get connected to jobs, roommates, and events.
If you’re curious about my longer-form writing and occasional rants after working in the dating industry for 15 years, I encourage you to subscribe to my dating & relationship library!