Shabbat Roulette: A Twist on the Traditional Shabbat Experience


On February 22nd, Zoe Plotsky (Taste 2018), Jessica Siskin (Taste 2018), Carli Roth (Tech 2016) and Nate Auerbach (Music 2016) from Inside India 2018 hosted a Shabbat dinner experience for the New York City alumni community. We sat down with Zoe and Jessica to learn more about why they organized it, how they planned it and what lessons they learned along the way.

Team REALITY: What inspired you to launch Shabbat Roulette?

Zoe and Jessica: The idea for Shabbat Roulette came together in an Uber in the middle of Mumbai. As Music, Tech, and Taste journey alumni from different years, we didn’t all officially meet until we went to India with REALITY and JDC Entwine, and as we rode in Mumbai’s signature traffic towards dinner, we began wondering why it had taken so long for all of us to come together, considering we all live in New York and share common interests and even mutual friends. We realized that we’d even been at some of the same REALITY gatherings, but since we were so busy catching up with friends we already knew or participating in structured programming, we hadn’t had a chance to connect. We wanted to change this by breaking down the typical structure of many of the events we’d attended for a unique, more intimate experience.

We knew that with so many incredible alumni across different journeys, we could tap into that mix of smaller communities to create a special, comprehensive community experience when we were back in New York. We immediately thought of Shabbat as the perfect venue for this.

Team REALITY: Why Shabbat?

Zoe and Jessica: In short, we love Shabbat. It’s a time to pause and gather with your community in reflection. But really, ask any REALITY alumni their favorite part of the journey, and nine times out of ten you’ll hear the final 2 days — beginning with Shabbat dinner. Since most of the Shabbat dinners in the NYC Hub had been bigger in nature, we wanted to see what would happen if we invited the NYC REALITY community to smaller, home-hosted dinners with support from OneTable — the partner for REALITY on Shabbat experiences.

We saw Shabbat Roulette as a new and engaging way to celebrate Shabbat with a community of people so great you haven't even met them yet. Our aim was to connect alumni with other local REALITY alumni by facilitating multiple curated, simultaneous Shabbat dinners that convene post-dinner for a joint after party. We sought to leverage alums’ trust in the quality of REALITY community members to encourage them to meet more people, and felt that the best way to strengthen the community as a whole is to create more small bonds between members.

Team REALITY: Where did the Roulette in Shabbat Roulette come into the plan?

Zoe and Jessica: We called the event Shabbat Roulette because we liked the metaphor of spinning a wheel to find your dinner. Of course, we were a bit more curated than that! We knew that everyone in the REALITY community shared one thing in common — they’d signed up for a week in a foreign country with 50 strangers. Signing up for a single dinner with fellow alumni in your own city would be easy!

Team REALITY: What inspired you to add a philanthropic piece to your dinners?

Zoe and Jessica: We asked our guests to make a donation to SEWA (The Self-Employed Women’s Association). We met with SEWA while in India, and learned about JDC's partnership with SEWA in the poverty-stricken Tapi district of Gujarat. SEWA provides one of the most vulnerable groups of women in India with critical support in all areas of their communal and individual lives. This support includes health services, education awareness, insurance, organic farming inputs, and local marketing linkages. By piloting this program in one of the poorest parts of India, JDC and SEWA hope to design a new income generation model that can be replicated across the country, providing vulnerable women with an opportunity to increase their income as well as their independence. We raised over $1,000 for SEWA through Shabbat Roulette, and that’s just one of a number of ways our group is working to raise money for SEWA overall (learn more here!).

Team REALITY: How did you engage alumni as hosts and recruit dinner guests?

Zoe and Jessica: We identified three needs: 1) physical space, 2) hospitality skills, and 3) understanding of Shabbat, or interest in learning more about Shabbat rituals. Working with the REALITY team and our cross-journey networks, we reached out to a few people and invited them to host. Once confirmed, we gave them slight parameters (mostly around timing and information about SEWA) and asked them to create their own dinners via the OneTable platform.

We sent out the invite to the entire REALITY NY community, and When guests RSVP’d, we asked them more about what they like (a neighborhood, dietary preferences, a buddy, etc.), and then we matched all of the guests to different hosts. After we curated all the dinners, we asked each host to reach out to their guests with a reminder and any additional details about what to expect. After dinner, all of the groups convened for a celebration for the REALITY community and beyond.

Team REALITY: How did the event go, and what lessons did you learn along the way?

Zoe and Jessica: Ultimately, we had guests from 11 journeys, helping to facilitate intimate connections across industries and journeys. We are now more energized to continue making this community cozier through Shabbat Roulettes, and more intimate Shabbat dinners. As the community grows, we will continue to value the relationships we already have while continuing to connect with new alumni. We look forward to continuing to attend programmed events and know we will spend a lot of time catching up with people we already know, but we hope to make Shabbat roulette a staple as the community grows to make sure we maintain the intimacy that makes it so special!

Team REALITY: What advice do you have for alumni who might want to host Shabbat Roulette in their hub city?

Zoe and Jessica: Do it! Unlike larger events that require securing a venue and catering to accommodate big groups, it’s easy to source space and nourishment from within the community, keeping the overhead low so participation fees can go towards philanthropic efforts. When announcing your plans, it helps to remind people that they didn’t know anyone when they arrived in Israel for REALITY and left with a new community, and that the same thing should happen at Shabbat Roulette. We can both attest that we’ve stayed in touch with people we met at Shabbat Roulette that we might not have had the chance to get to know at bigger events, and the experience of attending allowed us to feel more connected to the broader REALITY alumni community.

The Charles and Lynn Schusterman Family Foundation is proud to empower emerging leaders to explore their values, identity and new ways to strengthen their communities. We believe that as we work together to repair the world, it is important to share our diverse experiences and perspectives along the way. We encourage the expression of personal thoughts and reflections here on the Schusterman blog. Each post reflects solely the opinion of its author and does not necessarily represent the views of the Foundation, its partner organizations or all program participants.