Pessimistic at Best

If you're chemically addicted to watching Chicago apartment tours on TikTok, this episode is for you! Get to know the man behind the curtain (or camera), from his least favorite household chore to his go-to Chipotle order. Dean and I take to the podcast to chat about how he got started doing his now infamous apartment tours, the ups and downs of social media, the challenges that come with gro...

You know you've been spending too much time indoors when you go outside and think to yourself, man it rocks out here!! James and I take to the podcast to chat about the benefits of being curious, the worst smells at the Logan Square Farmer's Market, and the absolute freaks that think it's okay to litter. Support the show THERE'S MORE WHERE THAT CAME FROM:   FOLLOW THE PODCAST I...

Now, I'm not here to tell you to fake it until you make it, but sometimes the key to being hot is simply acting hot!!! Pat and I take to the pod this week to share our mutual love of Google Calendar, divulge our early interest in retirement, and discuss doing the hard work of confronting our emotions. Support the show THERE'S MORE WHERE THAT CAME FROM:   FOLLOW THE PODCAST Instagram: @pe...

If it's one thing about us, it's that we're never going to let a man tell us what to do. Dante and I take to the podcast to sing the praises of this summer's pop girlies, lament the horrors of moving, and ruminate over the audacity of people at the airport. Join in, you know you wanna. ;) Support the show THERE'S MORE WHERE THAT CAME FROM:   FOLLOW THE PODCAST Instagram: @...

Did you know that humans cement their taste in music in their late twenties? Feeling incredibly blessed to live during a time in which my Saturn Return overlaps with Brat Summer — formative years to say the least! Mickey and I take to the podcast to discuss the ups and downs of owning a fully developed pre-frontal cortex (try saying that five times fast!) and, more importantly, to talk mad shit ab...

The Olympics had us singing "Party in the USA" just before the Chicago Air and Water Show came along and knocked the red, white, and blue right out of us again — because that's where we simply must stand on business! Ciara and I take to the podcast to celebrate Team USA and triangular-shaped buildings before we debate over our differing tastes for spooky szn and so much more — join...

We're baaaack, and much to everyone's dismay, we're better than ever! Join us for our season kick-off where James and I take to the pod to share in our love for swimming and our distaste for servers that overcompensate, and stay for an impassioned speech about how much I hate having to get up out of my seat when the person next to me on a flight has to use the restroom. Did you miss...

Is there anything better than seeing how the other half lives? If you enjoy treating yourself to celebrity home tours or listening to Dakota Johnson ramble on about false fruit obsessions, this episode is for you! Join us for a silly little conversation about Architectural Digest tours, the impending cicada boom, and the horror of discovering you have self-tanner hands. Support the show THERE&apos...

Sitting around the campfire is all fun and games until you become the chosen one and suddenly you're blind and both of your lungs collapse. Not to mention the lingering smell that adheres to everything you own — 'tis the season! James and I jump on the podcast to fawn over reunion videos, complain about smoke in the eyes, and argue over whether being late is culturally acceptable, join i...

Did you have a Christian phase? Have you also been arrested? I'm not saying there's a correlation, but let's look at the facts. Kyle and I self-identify as total sweethearts, but previously we were singing hymns and doing time. Join us for an honest conversation about the joys of dating, the burden of having a downstairs neighbor, and the harsh reality of it being an election year....

Picture this: It's 1:30 am, the lights come on, 'Closing Time' starts playing over the speakers, the bartenders have turned on you and there are two big burly guys telling you that you can't wait for your Uber inside. Is there anything worse?  I think not! Owen, James, and I take to the podcast for a deep and intellectual conversation about e-cards, eye doctors, expiration date...

Do you suffer from road rage or are you medicated? As a proud passenger princess myself, I typically abstain — but I understand the urge, driving is hard! Let it out, bestie! Dylan and I take to the pod to grumble about physical labor and publicly shame people who don't use their turn signals. Join in the fun, you know you want to. ;)  Support the show THERE'S MORE WHERE THAT CAME FROM:...

Did your high school have an open campus lunch or were you one of the unlucky ones? I hate to break it to you, but there is truly no experience that could compare to piling seven deep in a friend's car and zipping across the street to the mall food court for a slice of Rocky Rococo's pepperoni pizza and a pink lemonade. None! Join us for a silly little conversation about drunk McDonald&a...

Do you ride or die for Steve Jobs? Don’t worry, you’re safe here! Jake and I take to the podcast to discuss the finest technological advances of our lifetime (caller ID & iPhone cases with kickstands) while simultaneously confessing our unyielding need to touch grass and perhaps create something with our hands, because we contain multitudes! Support the show THERE'S MORE WHERE THAT CAME F...

I need to apologize to anyone who listens to this episode and purchases a ticket to Lollapalooza because I said Phoebe Bridgers is on the lineup. That is utter misinformation, she's probably busy that weekend, and I have no idea where I heard this rumor or why it came out of my mouth. Please forgive me! Okay, now that we got that out of the way. If you're NOT mad at me, consider joining...

Do you have a nickname? Was it self prescribed or bestowed upon you? Do you prefer your god-given name? What if god isn’t real, then what? So many questions!  While you contemplate your answers, why not join us for a silly little episode about the magic of visiting your local Asian supermarket, the terror of encountering your local Christian Bible thumper, and the harsh reality of taking an overwh...

Becoming an adult means getting a printer for the home and we're officially shedding our youth today, folks. James and I take to the pod to discuss the versatility of breakfast sandwiches, lament over the incredible inconvenience of having to type in a password, and persecute anyone who willingly leaves the house with a chipped mani. Sorry, not sorry!  Support the show THERE'S MORE WHERE...

What ever happened to getting all gussied up for a night at the theater? We used to have class, we used to have taste, we used to have culture — now all we've got are a bunch of hussies wearing their "Kiss me, I'm Irish" t-shirts to the Saturday evening showing of My Fair Lady. Join us for a silly little conversation about comfort shows, modern architecture, and boring losers w...

Not to be dramatic, but I would happily lay down my life for the man who sings songs to his goat on TikTok. Have you had the pleasure of encountering this sweet creature? His gentle spirit, his adoring fan, I simply can't get enough! Join us on the pod for a silly little conversation about whether our reverence for animal videos spans generations and stay for my hot take on what it takes to g...

Did you know that if you get bad news during a tarot reading it's your fault? Anyway, Jasen paid 30 dollars for a woman to tell him he was destined to get famous by coming on my podcast, so here goes! Join us for a silly little conversation about rollerskating, apartments with no personality, and reality TV's latest innovation, The Traitors. You're going to love it, seriously! Suppo...

When it comes to condiments, how refined is your palate? I'm a mustard girlie, but I admittedly still fuck with ketchup, is that okay? You can be honest! Join us for a silly little conversation about our favorite mayo-based dressings, our biggest red flags, and our thoughts on the ugliest running shoes. Support the show THERE'S MORE WHERE THAT CAME FROM:   FOLLOW THE PODCAST Instagram: @...

Besties, are you tweaking out or are you locked in? We're asking the tough questions today on Pessimistic at Best! Personally, I'm tweaking but I'm trying sooo hard to lock in. Join us for a comically unstable conversation about bidets, movie trailers, and the Twitter comments section. SPONSORED BY Magic Mind: magicmind.com Support the show THERE'S MORE WHERE THAT CAME FROM:  ...

Are you a cat person or a dog person? I'm not trying to start drama but personally, I've never seen a dog boots the house down, just saying!!! Zoe and take to the podcast to fawn over the feline's primordial pouch, trash talk Chicago winters, and share our hot takes on hairless pets — join in if you're feeling frisky ;) Support the show THERE'S MORE WHERE THAT CAME FROM:  ...

It's 2024 and the rumors are true, I'm popping off this year! So sorry you had to find out like this, destiny is calling and I'd be a fool to let her go to voicemail, as they say! We're back with a new season and a slightly new episode format that I'm so excited to finally pump into your sweet little ears. This season we're starting a new segment on the pod called, &q...

We’re just another internet couple creating content for our adoring fans. It’s hard work, but somebody’s got to do it. So, here we present you the final episode of season six. We’re celebrating Festivus a little early this year and airing our grievances with one another right here on the pod, so join us in discussing the things we like the least about each other. The perfect start to a merry holid...