Inspired by The 36 Questions That Lead to Love and Table Topics, we created cards to inspire conversations at our own apartment.

Level I
Questions you could ask anyone at a cocktail party
- What’s a highlight from this past week?
- What’s a lowlight from this past week?
- What’s something you’re looking forward to in the upcoming week?
- What have you been listening to lately?
- What have you been reading lately?
- How did you decide to come to New York?
- What do you love and hate about New York?
Level II
Questions that you could still ask in a work environment
- What’s an irrational behavior that you have?
- What’s something that has recently changed priority for you?
- What’s something you value more than others?
- What would constitute a “perfect” day for you?
- Tell your life story in 5 minutes.
- What is the greatest accomplishment of your life so far?
Level III
Questions that require a personal answer
- What do you know so far about your life purpose?
- What’s your “hamming problem” — the biggest problem that you’re trying to figure out for your life right now?
- If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
- What is your relationship with your family like?
- What roles do love and affection play in your life?
Level IV
Questions involving our uglier sides
- Who’s someone with whom you have a disagreeable relationship?
- What kind of people do you envy?
- What’s something you’ve done that you regret?
- What are you afraid of right now?
- When did you last cry in front of another person? By yourself?
- What is your most treasured memory?
- What is your most terrible memory?
Level V
Questions best asked when you’re already comfortable
- Who are the 5 people you spend the most time with? What kind of people are they?
- “Only in the darkness can you see the stars.” – MLK Jr. What is a dark or unhappy part of your past that has constructively shaped who you are today?
- Draw a “lifeline” where the x-axis is time and the y-axis is happiness. Discuss the highest and lowest times in your life.
- Share something you think is a positive characteristic about the other person / the people next to you.
- Share a personal problem and ask for advice on how they might handle it. Also, ask them to reflect back to you how you seem to be feeling about the problem.
Thank you to Jennifer for gifting the blank cards that inspired this project.