Welcome to Pessimistic at Best, a podcast for those with a penchant for frequent frustrations, personal gripes, unpopular opinions, honest observations, and the like. Hosted by Sam, your resident Pessimistic Patty, this weekly show dares to ask the question—have we tried listening to women? Each week, Sam sits down with a guest to explore the good, the bad, and the ugly. A surprisingly good country album by your favorite pop artist, a bad bang trim you gave yourself during a manic episode, a ...
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Sam Georgson Podcasts
Send us a love letter (or hate mail, your choice!) Picture this: the year is 2006, and Disney's three-episode crossover series 'That's So Suite Life of Hannah Montana' is releasing its first episode at 8/7 central, and you're SAT, ready to witness a piece of history. James and I take to the podcast to nerd out over iconic crossover episodes, spiral…
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Send us a love letter (or hate mail, your choice!) We're all secretly afraid that our kids will be losers, and listen, I'm here to tell you that if that happened to me? I wouldn't talk to him either! James and I jump on the podcast to toast to bar games (think pool, darts, shuffleboard, yktv!!!), lament the fact that our thousand-dollar pocket comp…
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Send us a love letter (or hate mail, your choice!) Why did breakfast box itself into such narrow thinking? The day's most important meal could be so much more than eggs, if only we let it become fully realized!!! Sadie and I jump on the podcast to chat about nicknames we love, bike lanes we loathe, and our deep dissatisfaction with the oppressive e…
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Send us a love letter (or hate mail, your choice!) If there's a viral snack collab unfolding, Lilly is on the scene! Mountain Dew x Flamin’ Hot Cheetos? Sign her up. Swedish Fish Oreos? She's buying 'em, and nobody can stop her, damn it! Lilly and I take to the podcast to indulge in absurd snack innovations, spiral about accumulating too much “stuf…
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Send us a love letter (or hate mail, your choice!) Who eats sardines straight from the tin, carries a wad of rubberband-bound singles, and is in “talks” with the Italian government? Depends on who's asking. Adam and I take to the podcast to toast to tinned fish, raise a stink about early morning construction, and pour one out for the many folks who…
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Send us a love letter (or hate mail, your choice!) It’s important to remember that the SUR experience has little to do with the food. Its true specialties lie in campy ambiance, overpriced cocktails, and the chance to share a room with some of reality TV’s messiest players—pure bliss! Matt and I jump on the podcast to honor our favorite divorce alb…
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Send us a love letter (or hate mail, your choice!) Picture this: You're freshly thirteen, you've got your brand new Ocean Pacific swimsuit on, and you're patiently making your way up the wooden staircase with your tube in hand. What's waiting for you at the top, you ask? None other than the Wilderness' most infamous waterslide, the Hurricane. Talk …
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Wrestling Is the Straight Man’s Drag
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Send us a love letter (or hate mail, your choice!) Name something more c*nty than a giant chiseled man with a spray tan and platinum blonde blowout strutting to the ring in a bedazzled outfit to the tune of "Real American"—you can't! Rohan and I take to the podcast to celebrate grown men finding an outlet for self-expression, reject the creation of…
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Send us a love letter (or hate mail, your choice!) If I have to use my own cellphone to pull up the menu at the restaurant, I'm clocking in because I work here now. I said what I said! James and I return to the podcast to celebrate Flow's Academy Award for Best Animated Feature (s/o to Latvia, a real place that exists!), dismantle the Digital Menu …
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Send us a love letter (or hate mail, your choice!) I recently found myself feeling insecure about my Hydro during a Zoom call full of Stanleys and decided enough is enough! Screw your trendy water bottle! Unless you're still chewing on your Camelbak straw, like seriously, it's time to move on. James and I hit the podcast to celebrate mixing metals,…
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Send us a love letter (or hate mail, your choice!) Picture this: The year is 2025 and you're making the active choice to jump back on the reading train after it dawns on you that you've forgotten how to do anything besides watch TV. Sound familiar? If so, you're safe here! Grace and I take to the podcast to celebrate Chelsea Handler's new book, I'l…
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Send us a love letter (or hate mail, your choice!) Have you ever been out to eat when your waiter suddenly goes missing, only to reappear on stage, mic in hand, bringing down the house? It's like, sure you wanted another martini, but ultimately you're happy they're having their moment! Owen and I take to the podcast to celebrate servers with secret…
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Send us a love letter (or hate mail, your choice!) Were you normal, or were you spending your iTunes gift cards on Glee covers? Don't worry, you're amongst friends! Donnie and I take to the podcast to celebrate authenticity, stress over our favorite strategy-based reality TV game shows, and complain about men, naturally! Btw, did we ever figure out…
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Send us a love letter (or hate mail, your choice!) Brunch is something you plan in advance. It's an event you prepare for. Heck, you might even put on a cute outfit! Breakfast, on the other hand, is thrust upon you (whether you like it or not!) Luke and I take to the podcast to rejoice in the pleasure of breakfast with your friends, complain about …
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Send us a love letter (or hate mail, your choice!) Everyone can be someone and anything can be cool — and isn't that beautiful? Sure, there will always be pop stars with seismic fanbases like Taylor Swift and Beyoncé, but the "mainstream" is over, you heard it here first! James and I take to the podcast to dive into the death of the mainstream, pro…
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When Your Pants Get a Little Loose at the Knees
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Send us a love letter (or hate mail, your choice!) We're back, babies! And ever so grateful to be back in your ears each week. We missed you terribly — what a long two months it has truly been. Much to catch up on, so let's take it from the top! James and I take to the podcast to share our favorite onomatopoeias, lament over the humiliation of runn…
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Send us a love letter (or hate mail, your choice!) Friendly reminder that the absolute worst thing you can do is tell someone they seem tired, it never goes over well. Instead, you could try, "You look like shit," or "What the hell is your problem." This week James and I take to the podcast to encourage more themed parties, commiserate about just h…
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Send us a love letter (or hate mail, your choice!) Great news team, becoming a better person is actually incredibly easy! Follow our 5-step process and you'll surely go straight to heaven or be reincarnated as something really cool or whatever. In this week's episode, James and I take to the podcast to celebrate the versatility of the fist bump, co…
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Send us a love letter (or hate mail, your choice!) Have you ever been to the state of Delaware? Because me neither, and I have no designs on visiting! Devonte and I take to the podcast to celebrate finding fulfillment in our respective careers and shared community, to burst the bubble that is traveling for work, and to throw shade at the CTA. Get s…
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Send us a love letter (or hate mail, your choice!) Playing dumb is all fun and games until you're on the receiving end of such behavior — we said what we said! Aidan and I take to the podcast to sing the praises of our favorite fast-food chain (Taco Bell, duh!), deliberate over the appropriate way to deplane after a flight, and expose people for we…
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The Quest to Become a Morning Person
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Send us a love letter (or hate mail, your choice!) Are you buying into the propaganda that morning people are more productive? Because we’ve sold our souls and signed on the dotted line. Manu and I are just a couple of night owls on the quest to become early risers and get that damn worm if it's the last thing we do! Join us on the podcast for a co…
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Send us a love letter (or hate mail, your choice!) If you listen to this episode I'm sorry and if you make it all the way to the end something is literally wrong with you! Truly rubbing my last two brain cells together for this one, enter at your own risk! James and I take to the podcast to relive the golden age of computer games, lament the hassle…
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We're Not Friends We're Business Partners
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Send us a love letter (or hate mail, your choice!) We're starting a support group for people who have had to execute a Facebook Marketplace pickup while viciously hungover—do you want in? Luke and I take to the podcast this week to chat about our favorite micro-influencers, our aversion to submitting maintenance requests as renters, and our deep di…
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Send us a love letter (or hate mail, your choice!) If it's one thing about us, it's that we're going to buy tickets to the concert! Annie and I take to the podcast to share in our love for being "woo" girls at our favorite live shows, to bitch about music venues that don't have water stations, and to shame our friends who don't know how to purchase…
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Send us a love letter (or hate mail, your choice!) How many hotdogs could you reasonably consume in a 2.5-hour sitting? The 9x9x9 challenge has officially met its match, and I have the absolute pleasure of hosting our fearless champion on this week's podcast! Neil and I take to the pod to chat about the joys of trying your hand at something new, th…
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Send us a love letter (or hate mail, your choice!) Is it just us, or do all Midwestern dads have the same undeniable penchant for building elaborate underwater ecosystems within the home? What’s the story there? This week on the podcast Grace and I share our affinity for Autumn's rebrand, our loathing of overcrowded spaces, and our tendency toward …
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Send us a love letter (or hate mail, your choice!) 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 no…
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Send us a love letter (or hate mail, your choice!) 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 l…
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Send us a love letter (or hate mail, your choice!) 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 emotio…
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Not Going to Let a Man Tell Me What to Do
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Send us a love letter (or hate mail, your choice!) 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. ;) Get silly…
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Send us a love letter (or hate mail, your choice!) 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 devel…
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Send us a love letter (or hate mail, your choice!) 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 buildi…
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Send us a love letter (or hate mail, your choice!) 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 o…
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Send us a love letter (or hate mail, your choice!) 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 impendi…
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Send us a love letter (or hate mail, your choice!) 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 …
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Send us a love letter (or hate mail, your choice!) 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…
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Send us a love letter (or hate mail, your choice!) 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 …
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Send us a love letter (or hate mail, your choice!) 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…
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Send us a love letter (or hate mail, your choice!) 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 pizz…
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Send us a love letter (or hate mail, your choice!) 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 wi…
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Send us a love letter (or hate mail, your choice!) 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 forgiv…
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Send us a love letter (or hate mail, your choice!) 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 …
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Send us a love letter (or hate mail, your choice!) 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 l…
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Send us a love letter (or hate mail, your choice!) 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 …
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Send us a love letter (or hate mail, your choice!) 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 …
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Send us a love letter (or hate mail, your choice!) 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 r…
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Send us a love letter (or hate mail, your choice!) 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 s…
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Send us a love letter (or hate mail, your choice!) 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. Get silly wi…
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Send us a love letter (or hate mail, your choice!) 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 yo…
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Send us a love letter (or hate mail, your choice!) 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 litt…
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