The strange phenomenon of watching your dream come alive in front of you, nbd.
Alternate title: dinner went great.
On Wednesday, I hosted 20 strangers for dinner.
I was terrified that, with a bigger group, it was going to be awkward, that people wouldn’t connect or be comfortable enough to really share. I was worried it was too big, I was reaching too far, and that the whole thing was going to be a big flop.
It went even more beautifully than I could have imagined.
I started hosting monthly dinners with my friend Ryan at his hair studio in 2018. We had this vision of hosting conversations that skip the small talk and work talk, and thus, Dinner With Strangers was born. From the very first dinner we hosted, there was this palpable magic; I didn’t know what it was, but I knew I wanted to follow it. I wonder if I could make this my job, I thought, and immediately laughed at myself.
We hosted 15 or so dinners before I moved to San Francisco at the end of 2018, where I worked in an office for exactly 3 weeks before I told my boyfriend at the time, for whom I had moved across the continent, that I re-remembered that I am not meant to work a job with a salary, I am meant to live a strange artsy entrepreneurial-ish life and wanted to figure out a way to start the dinner series in San Francisco. To which he said, basically, that is absolutely ridiculous and terrifying and impossible, why would I do that. (Side note, if your partner says something is smothering their soul and something else makes them light up and they’d like to do more of the thing that lights them up, don’t tell them that thing is ridiculous and terrifying and impossible. Just a PSA.) So I tucked this dream in a box and buried it in the shelves of my little heart for a year while I tried to be professional and reasonable. But the dream inside the box kept knocking.
I broke up with that guy and I quit my serious and professional and reasonable job and I moved back to Toronto to somehow turn this dinner series into a business. And of course that was in February 2020, five weeks before the world ended, and dinner and strangers ceased to be a thing.
Which is all to say, it’s been a long road to get to Wednesday.
I’m working with this new beautiful space at Roof Garden, and hired chefs for the first time (hallelujah, what a gift!) and figured out what needed to be adjusted to format the night for 20 people instead of the usual group of 10 that I was used to. People bought tickets and showed up with their own unique magic. They subscribed to this a-little-bit-crazy thing of sharing personal stories with complete strangers. And off we went.
Within thirty minutes of the event starting, I realized that it (probably) wasn’t going to be a horrible night, and that things were going really well. It’s a bit weird to stand in a room of your own making, this weird dream to make space to connect with others. To have dinner with strangers and share something real. I’d love to tell San Francisco Jess how the story turned out.
I just wanted to take a minute to highlight how big of a deal it is that Wednesday happened, and the long, long road it took to get there. Our dreams arrive and come to fruition slowly and in surprising ways. Sometimes they spend a bit of time in a cardboard box for a while. Dreams are patient things.
I’ve also been really overwhelmed with gratitude for this community (hi, that’s you) - I don’t know if you realize how much you’ve given me - every time you share a post or send a post to a friend or comment or read through a newsletter or sign up for a workshop or buy a ticket or send a message saying you wish you could buy a ticket… all of those interactions have quite literally changed my life. Thank you for making it possible for me to go after this wild, weird dream life of mine.
On a related note…
We have our monthly In Good Company writing workshop on Sunday morning at 10:30am! Come write and (optionally) share your work :) Zoom link will go out tomorrow.
On Wednesday, Sept 27th, I’m hosting a ‘How To Host A Dinner Series’ workshop at 7pm EST on Zoom - learn about the elements of a great dinner, who to invite, what to make, how to ask good questions, some of the roadblocks I’ve had and solutions I’ve come up with, and ask me questions! It’s $40 for the night, unless you’re a paid Substack subscriber ($5/month), in which case you’ll get the Zoom link automatically!
I’m cohosting a writing & yoga retreat on Wolfe Island, Ontario, on October 20-22, and we’ll have a Dinner With Strangers dinner on the Friday night! You can register for that here.
Thanks again for being here, it truly means the world.
xo jess.
Congrats Jess! Also I love this quote: "Sometimes they spend a bit of time in a cardboard box for a while. Dreams are patient things." ❤️
Congratulations :)