Stranger Dinner - Round Two.
Earlier this month, I flew a complete stranger (but a longtime subscriber) all the way from Boston to Los Angeles for dinner. And, after three hours together (filled with seafood and stories), I believe Danielle and I left that dinner as new friends.
In late 2016, I had this idea of traveling somewhere with someone I absolutely didn’t know — just to see how it would go — because, in my own experiences, I consistently found that the random people I met while traveling were often more memorable than the places themselves. And, after so many years of sharing my travels and life on Instagram, I thought, “Why not just take someone who’s followed me and supported my work along for the ride?” And, like this, the idea for “Stranger Danger” was born . . .
For those of you who might be unfamiliar with it, Stranger Danger involved flying myself and a complete stranger out to a city of their choosing to spend three or four days together, while I footed the entire bill. The “contest” (if you want to call it that) was open to any and all subscribers of my old “Dear Captain” newsletter.
To enter, you had to submit a short essay describing where you’d like to go (any city in the U.S. was fair game) and why. I would then read through each and every email received before selecting the person that I felt would get the most out of the experience . . . Someone who had always dreamed of going to New York for the holidays, someone who craved the polar opposite of their hometown, or someone who could seriously benefit from simply getting out of their comfort zone.
In this way, I ended up in New Orleans, Saint Augustine, Austin, Detroit, and Boston with people that I’d never met before connecting in the airport. And, guess what? It was fucking awesome. I had a lot of fun doing it, I learned a lot (these trips often got me out of my own comfort zone), and it felt good to share the experience with someone that I felt really deserved (or needed) it.
From 2017 to 2019, I completed five rounds of Stranger Danger before my lawyer advised me to stop because I was putting myself at too much risk — to which I responded, “Well, yeah, ‘danger’ is in the name.” And I had every plan of going forward with five more rounds, but the second half of 2019 took a few unexpected turns, becoming a hard year for me personally. And, well, 2020-2022 was a terrible time to travel. So, Stranger Danger kind of just faded away . . .
But I always wanted to bring it back in some way, and this led me to the idea for “STRANGER DINNER” — and it’s now time for ROUND TWO.
Here’s what STRANGER DINNER R2 will consist of:
I’ll fly you out to Los Angeles (where I currently live), or cover any other form of transportation to get you here: train, Uber, bobsled, hang glider, etc.
I’ll put you up in a nice hotel for a night or two (don’t worry, I’ll pick something historic and simply fucking cool — trust me on this, I know what I’m doing).
We’ll meet for dinner at a restaurant of your choice, or one of my own — it’ll be up to you (obviously, I will cover this as well).
This dinner will allow us to spend a few hours together, talking about anything and everything that comes to mind. If you have something you’d like to ask, just ask. If you just want to hang out, we’ll hang. This will also be my way of saying “Thank you” for all the support that I’ve continually received over the years.
HERE’S HOW TO ENTER:
Upgrade to a paid subscriber to this Substack (any tier is qualified).
Send an email to STRANGERDINNER@SGRSTK.COM with the following information:
A bit about yourself. No more than 100 words. Anything more than that and we are no longer “strangers,” which kind of defeats the purpose.
Answer this question: If you could have dinner with any person (alive or dead), who would it be, and why? I know this is a common, and perhaps even cliché question, but I do believe there’s a lot revealed about an individual by those chosen to sit at their table.
That’s it. Once you’ve done that, you’re officially entered. You have until THE END OF APRIL to send your email.
I will read through every entry, contact and announce the winner by the end of May, then fly them out shortly after (if you’re selected, I’ll work with you to see what works best for both of our schedules).
I’m looking forward to reading through all of your emails and getting together soon for some good food and good conversation.
Thank you for all the continued support.
—KC