August 22, 2026
Have deep conversations with curious strangers.
Join 2 monthly 60-minute online conversations in a room of 3-4 people. We send you one short essay, deep questions, and organize the room. So you can skip the small talk and go deeper.
60 minutesOnline3-4 people in each room
Upcoming conversations
Two Saturdays a month.
10 AM Pacific Time
September 5, 2026
How to Balance Life While Still Being Human
September 19, 2026
Who Do I Want to Be When I Grow Up?
How it works
How it works.
Join the Zoom call at the scheduled time
Open the Zoom link and meet the people in your room. There is nothing to prepare beforehand.
Read one short essay
We share the essay during the call and give everyone time to read it. It becomes your shared starting point.
Talk in a room of 3-4
Use the questions as guidance, follow where the conversation goes, and make space for every person in the room.
Founding membership
Join while the club is new.
Come for two small-room conversations each month, then keep talking with the community between calls.
30 spots left at the founding price0 of 30 claimed
Then the regular price begins: $20/month or $200/year.
Your founding price stays with you while your subscription remains active. If you cancel and rejoin later, the current regular price applies.Monthly
Save 40%$12/ month
Regular price $20/month
- 2–4 conversations every month*
- Essay and questions shared during each call
- Rooms of 3-4 people
- Private Discord community of like-minded people
- Cancel before your next renewal
Yearly
$8.33/month$100/ year
Regular price $200/year
- Everything in monthly, just cheaper
* Right now, there are two conversations each month. Once the club reaches 30 members, we'll have 4 convos per month
FAQ
How many conversations are there each month?
Right now, there are two. Once the club reaches 30 members, there will be four conversations every month.
Where are the calls held?
The calls are held on Zoom. We send you the link beforehand; open it at the scheduled time and we will place you in a small discussion room.
What happens before a conversation?
Nothing. Just join the Zoom call at the scheduled time. We send you the link beforehand, then share the essay and questions during the call. You do not need to read or prepare anything in advance.
Do we have to follow the questions or answer every one?
No. The questions are small guides that make it easier to begin and help the conversation go deeper. You can answer some, follow an interesting tangent, or answer none of them.
What if I do not want to answer a question?
Then don’t. You never need to answer or do anything you do not want to do.
Are there only 3-4 people on the whole call?
There are 3-4 people in each discussion room. The call can have hundreds of people, but your conversation stays small.
What happens in the Discord community?
Members can continue conversations, share thoughtful things they have read, and meet other curious people between calls. Access is included while your membership is active.
How does the 30-day guarantee work?
Try the club for up to 30 calendar days after your first membership payment. If you didn't like it - cancel and ask for a full refund. You do not need to give a reason.
Do I need to be outgoing?
No. The reason we have essays and prompts/questions is to make it easier to have a conversation.
Is this group therapy?
No. Deep Conversation Club is a social discussion club, not therapy, coaching, or professional mental-health support.