Stranger Danger.

Monday Mutiny | 12.1.2025

In 2016, I had the idea of traveling somewhere with a complete stranger — just to see how it would go — because, in my own experiences, I consistently found that the random people I met along the way were often more memorable than the places themselves. And, after so many years of sharing my life on Instagram, I thought, “Why not 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 (the original iteration of what you are reading today).

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, usually somewhere around five hundred to a thousand, 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 . . .

In 2023, I wanted to do something along the same lines, so I threw the “Rum Tongue Social” (those of you who attended know it was a damn-good time). I rented out an entire bar on the most historic street in St. Augustine, I personally selected a band that had impressed me with their cover of “Sweet Dreams (Are Made of This),” and I had all the food and drinks anyone could ever want or demand. (Only one person had to be cut-off from the open bar, so I’d say the night was a success.) I loved getting a chance to meet everyone in a real-world setting, free of technology and the vicarious lens of social media (I was so caught up with talking that I didn’t even take a single picture from the night).

Now, the Rum Tongue Social was great, but honestly, it was too big. There were so many people in attendance that I left every conversation feeling like there was always more that needed to be heard or said. I didn’t really get a chance to talk with anyone for as long as I’d have liked — which is why I now have the idea for something new . . . Something both adventurous and conversation-focused. Something that will allow us to hang out for a bit. Granted, not as much as spending four days wandering around the French Quarter of New Orleans together, but this will be something that I can quite literally “afford” to do on a more regular basis.

I’m calling it: STRANGER DANGER DINNER.

Here’s what STRANGER DINNER 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, etc.

• I’ll put you up in a hotel for a night or two (don’t worry, I’ll pick something historic and 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. And, if all goes well, I’d like to start hosting these dinners/trips multiple times a year. So, if you’re not selected for this first one, there will most likely be another.

HERE’S HOW TO ENTER:

1. You must be a paid subscriber to this Substack (you can update your subscription at the button below). If you’re already a paid subscriber, you’re good to go.

2. 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: If you were on death row, what would your “last meal” be — and why? (I believe you can tell a lot about a person by the memories associated with their favorite foods and flavors.)

That’s it. Once you’ve done that, you’re officially entered. You have until the end of the year to send your email.

I will read through every email, announce the winner by the end of January, 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 soon and meeting one of you in person for good food and good conversation.

Thank you for all the continued support.

—KC