Have you ever been somewhere and the most beautiful, majestic, regal bitch you’ve ever lied eyes on walks in the room and your breath is snatched completely out of your lungs, your wig ripped from your bald scalp, and your credit score demolished right before your very eyes? That is the power that is Chicago. She is, and forever will be, THAT BITCH. Chicago truly is unlike anywhere else on earth. Whether it be the dramatic jagged skyline reaching into the clouds visible from miles away in every direction. Or the astounding density of architectural marvels that one can encounter in any block. Or the absolute queerness of it all. Or the trains (I mean as in transportation, ya fuckin’ freaks). And I looooooove trains!!! (and I mean both meanings, ya prudes!) I imagine one could spend a lifetime in Chicago and still never fully know her. She is deep, and layered, and loving, and creative, and scarred, and a hard ass, and full of emotion (good and bad) and sometimes smells weird. But honestly, who doesn’t??
I won’t bore you with a general history lesson of Chicago (because let’s be real, I am certainly not qualified to give one) but what I do want to do is share some of my favorite learnings from my last few times visiting. So sit down, take a bong rip, chug some Nyquil, do some Kegels, and get comfy cause it is Matt Storytime Hour™️!
October 2015. Imagine me, Matt, as a spry young twink just fresh out of college and ready to explore the world. Tax burden and heartburn and joint pain hadn’t yet made their appearance in my life (they make their grand entrance in the third act, so stay tuned!) Obama was still president. It bears repeating: OBAMA WAS STILL PRESIDENT. Anyways- Matt 1.0 (how I will refer to Matt in the 2015 era) flew to Chicago to spend time with some friends he’d made that year (Gerina, Brooke, Sam and Annemarie- I love you bbs!) Touching down in O’Hare, I was whisked away to the magical community of Naperville. Naperville is a suburb of about 150,000 people located about 30 miles west of downtown Chicago. Originally a pioneer outpost, Naperthrill grew quickly in the 1960’s – 2000’s as a major Chicago suburb. It’s leafy, and spread out, and has some nice suburban homes, and a cute lil’ downtown, and some office parks, and that’s about it. So why, you ask, was I whisked away here? Cause the ICONIC Shmancy (name modified to protect privacy lolol) (aka Brooke’s mom) lives there and she let me stay! (Thanks Shmancy!) Needless to say, most of the time in Naperchill was spent getting stoned to the mothafuckin’ bone with the girls and watching silly movies (aka the most perfect evening imaginable). BUT! Naperkill also happens to be right on a prominent rail line to downtown Chicago, meaning one can buy a cheap lil Metra ticket (I think back then it was like $1.50?) and BAM! You’re in the thick of it. So the next morning Matt 1.0 was on that train getting ready for ✨adventure✨. Now let me tell you- October in Chicago is GORGEOUS. It’s sunny, and warm (but with a tiny lil crisp in the air) and the cicadas have finally shut the fuck up and it’s just perfect. So I spent all day walking around downtown with the girls- going to the big reflective bean, checking out Navy Pier, getting some bomb ass food, just being GAY ya know? This was my first true Chicago day and let me tell you, it was pure magic. Over the next couple days I got to explore Boystown and Rogers Park (and spent a memorable evening at Berlin Nightclub where me and Annemarie took some cute photos- RIP Berlin </3 ) and got to explore many of the neighborhoods on the north side. Honestly my lil brain was just drenched in serotonin. Flooded. Serotonin-logged, if you will. So even within a few days, Chicago held my heart. It would be several moons before I would see my love again. Many unspeakable horrors happened during that time (aging. It was aging). But I was steadfast in my belief that I would return. And return I would.
Now, let’s fast forward just a lil tiddlywink to Matt 4.0 (Matt 2.0 and 3.0 will be discussed at a later time, don’t you worry. I can’t show all my cards at once, can I really now??) February 2026. Mere weeks ago. Imagine it- a much less spry, much less twink-esque Matt finds himself back in the windy city to celebrate my iconic friend Vee’s birthday (aka THEE VEE that I hosted drag brunch and karaoke with in Seattle. Yes, THAT Vee.) Vee’s incredible partner (shoutout Courtney!) plotted a big ol’ surprise party for Vee at their place right under Vee’s nose. And lemme tell you- there were some CLOSE CALLS. Someone seriously run this girl her Oscar. So picture this- as the birthday girl approaches, there’s a house full of like 30 drunk, loud ass queer people trying their best to not make a peep. Somehow, someway, by the grace of Grace Jones we didn’t blow our cover, but I truly thought it was a wrap. Now when I tell you I haven’t been to a good old fashioned house party like this in a MINUTE, I’m not joking. There were such good tunes, and snacks, and bevvies, and VIBES. I even drank! A cocktail! Made with gin, soda water and Emergen-C! Yes- the powder you put in drinks to not get sick- THAT Emergen-C. And like, you’re probably thinking wow what kind of foul bitch would do that. To which I answer- this foul bitch. And you know what? The drink did in fact slap. Not only did the flavor profiles really compliment each other, but my immune system was as strong as a Belarussian ox afterwards. Gin and Emergen-C literally will sterilize anything inside or adjacent to you, build up your immunity, give you a firm pat on the ass and send you on your merry way. Besides the bubble of absolute queer joy that was this party (srsly tho shoutout Courtney for putting that together), this most recent visit to America’s second city (suck a dick LA!) was fantastic. I got to spend some quality time with Charlie and Sam and we bopped around Wicker Park (which is a really cool lil area of town I’ve never been to!) The neighborhood is dense, has some incredible architecture, and has a bunch of cool stores. A standout was Myopic Books– three floors of pure unadulterated gay literary mayhem. I found some truly incredible finds like an old book of Erté visuals (for anyone who doesn’t know, Erté was a Russian-French artist who was a huge presence in the art and fashion scene in the 1920’s and is truly one of my gay creative inspirations). In addition, I got an Agatha Christie book cause duh, a 1970’s horror book about a cursed Bela Lugosi and Boris Karloff film that kills anyone who watches it, and a lil’ book called the Butch Manual. For obvious reasons. Besides gettin’ all booked up, I got to explore some of Wicker Park’s incredible architectural landmarks- a standout was the row of mansions along Pierce Avenue, including the Hermann Weinhardt house. Afterwards, we headed out to Garfield Park, a grand park on Chicago’s west side right off the green line. In addition to housing an absolutely incredible, ornate, 24-karat gold plated dome (seriously- its real gold. The folks working there confirmed it) Field House, the park is home to the massive Garfield Park Conservatory. Now, I don’t know if y’all have had the opportunity to visit Chicago’s parks, but this city does NOT FUCK AROUND WITH THEIR PARKS. Like the amount of work that went into constructing the ornate 1920’s Field House alone is insane. And it’s still being used as a gym and community center, which is awesome! Back in the day there was a horsetrack in the park where quaint old 1920’s folks would bring their horses to race around and get wasted and get into fights with each other, like turn of the century Nascar. But before we totally blow our load, we have to acknowledge the absolute star of the show here- the Conservatory. Built in 1907, the massive 4.5 acre complex of greenhouses contains thousands of plant species from around the world, including rare cacti, palms, ferns, bromeliads, orchids, euphorbia, and so so so much more. I cannot begin to explain to you in words how magical this place is. Each room is a massive, glass-enclosed fairytale wonderland transporting you to a faraway dreamscape with massive, alien-looking plants, ponds with glass art and koi fish, intricate wrought iron trellises with flowering vines, massive hanging staghorn ferns, and a room so fragrant with intoxicating floral scents that I wanted to pull out my poppers, chug the bottle, and pass out right then and there like Dorothy in the poppy fields in the Wizard of Oz. There’s also a gorgeous tiled Moorish-style fountain in the main room. So basically- it EATS. No, that’s not enough. It DEVOURS. If you’re visiting, I can’t tell you how important it is that you drop literally whatever it is you’re doing (except like, maybe your steering wheel if you’re driving, don’t do that) and head out to the park.
Anyways, because it’s been a while and I feel like I haven’t been able to be unhinged with y’all and it’s eating me alive from the inside, I wanted to share the story about the time I hooked up with someone while watching Shrek. I met this guy in Seattle who was from Reno and we immediately trauma bonded because, duh. We went and got some bomb ass margaritas and then went back to his place. One thing led to another and we’re fooling around and for some reason, my brain is like “Matt- ask him to put on Shrek for background noise”. So, because I’m very unwell, I ask him to do it. Like as we’re making out. So he does it and my mind, feeling at peace, is like ok we can continue. Fast forward a few minutes and we’re doing stuff (I won’t go into the details here because there may be CHILDREN reading this blog but honestly if there are how the actual fuck did you end up here I am so so so so sorry for the trauma I’m causing you please log off immediately, destroy your phone, and tell your parents you need to become Amish and distance yourself as far as possible from technology because in all honesty how the hell did you end up here? What possible keyword could a gen alpha person have searched to get here? Like I don’t have a single mention of anything related to 6 7 or Roblox or Billy Eilish or whatever the fuck they’re into. Ohmygod wait now those things are mentioned here and maybe their algorithm is like ‘hey check out this blog where this ancient homo mentioned 6 7 we think you’ll like it’. SHIT I just said 6 7 again. Oh well. Anyways, where was I?) Oh yeah, Shrek sex. So anyways we’re doing stuff and then in the middle of things all I hear is “DONKEH!!!!!!!” And like y’all, I’m sorry but no matter what may have been happening once I hear that phrase I am going to stare straight at the TV like a meerkat sensing a hawk overhead. Or like if I was a sleeper cell agent and DONKEH was my trigger word. Who knows, maybe it is? I guess we’ll find out tomorrow. Note for tomorrow Matt: if you wake up covered in someone else’s blood in a place you don’t recognize with no memories of the past 12 hours, then you have confirmation that you’re a sleeper cell agent and DONKEH is your trigger word. Anyways WOW this really got away from me! Maybe it goes without saying but after that night we never talked again. Ahh, fun times.
Moral of the story is: Chicago is a celebration of greatness, a layered story of loss, and a lighthouse of resilience. I plan on posting several more galleries (and stories!) of her as I spend more time there (also check out my other gallery I do have of her on the blog here). If there’s any one spot I recommend you go visit immediately it’s the Garfield Park Conservatory. And DONKEH fills me with insatiable bloodlust.
Chicago- Winter 2026


















































































































































































