The Tonight Show, cum dump etiquette, and some (actually good) queer art
I'm planting a garden by scattering seeds.
Hello Close Friends,
I wanted a place to share my still Substackable—potentially edible—delicious other thoughts that don’t fall under my usual sex and relationship umbrella.
In other words, I’m talking about my little musings and of course my journalism! You can read some of my recent stories with Block Club Chicago, the Chicago Reader, and the New York Times. The rest of my portfolio can be found on my website: charliekolodziej.com
I woke up last Monday to an email in my inbox from the Tonight Show with Jimmy Fallon. The producers from the show had seen my Block Club Chicago article on the Joe Keery lookalike contest in November and wanted to use a few of my photos as part of their upcoming segment with the Stranger Things star.
I thought it was a joke at first, but after a few google searches and some official looking paperwork, I signed those suckers away in perpetuity! You can watch the clip with Jimmy and Joe here. I made more $$ from those five seconds of screen time than I did from my original reporting and photography combined. Journalism is so silly!
2025 has been a slow start for the freelancing biz though. Unfortunately, the Chicago Reader has been hit by another budget crisis, one that there may be no coming back from. Several of my stories were recently cut and an editorial internship I was hoping to secure has been pushed to at least 2026. Please donate to the Reader if you want to protect local journalism in Chicago!
I still have a few pieces in the works however that I can’t wait to share with you! I am working on an interview for the Windy City Times with Lauren Leving, curator of Goldfinch gallery’s Jerome Caja exhibition. I’m also writing a 35th anniversary retrospective on Chicago’s Guild Literary Complex for New City Mag and a review of James Stewart III’s forthcoming novel Defiant Acts for the Chicago Reader.

I’m over two years into this whole freelancing thing, and I’m still trying to figure out what is considered a “normal pace” for publishing my work. Still I’m happy to be writing every day as I figure out what’s next for me in this little life. I told a friend recently that it feels like I’m grasping at straws and hoping they turn to bricks in my hand. Maybe I’ll build a house with them soon à la those three little pigs. (Consider this an open offer to ask me any questions you may have about freelancing in Chicago!)
I also published the second issue of my magazine, Write That Down!, with the help of my friends Taj Richardson and Tim Biondo. For those of you not yet in the know, WTD! is an archival zine project capturing the particulars of our current moment, both here in Chicago and in the world at large. We collect art, artifacts, and writing from people looking to tell stories about what is important to them and their communities. Our latest issue featured articles on Chicago’s queer nightlife renaissance, an essay from a Chicago Teachers Union representative, and art from up-and-coming local creatives. As we like to say, “If it matters to you, Write That Down!” You can read/purchase our Autumn ‘22 issue here and submit to our upcoming Winter ‘22 issue here.
I will also be back next week with a new Close Friends column just in time for Valentine’s Day! I’m currently deciding between writing about cum dump etiquette and what to do when you suspect your partner of cheating. If either of those inspired you, you can submit your own (anonymous) sex and relationship questions here. You can also read my latest column about getting over STI fears.
With all these things in the works, it feels a little like I’m planting a garden by randomly scattering seeds. Some of them might come up weeds, but only time will tell.
Lots of love,
A Close Friend
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Close Friends is a sex and relationship advice column from your local 20-something, Chicago queer. Subscribe for more (un)solicited advice in your inbox and fill out the request form with your most pressing questions. Mwah*