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Pessimistic at Best

Author: Sam Georgson

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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 military homecoming video on the internet that made you ugly cry. The list is endless, and therein lies the beauty. Come on in, we saved you a seat!

152 Episodes
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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 the reality of women's healthcare, and clap back at people who pick on picky eaters. Get silly with us on social: FOLLOW THE PODCAST Instagram: @...

Death of the Mainstream

2025-02-1101:03:49

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, protest our apparent collective dedication to ignoring the human desire to hibernate, and shame TV and movie franchises that refuse to let a good thin...
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 running to catch the bus, and complain about pants when they inevitably get a little loose at the knees after a long day of wear. Get silly with us o...

You Seem Tired

2024-11-2631:15

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 how much it sucks to throw up, and to render our final verdict on the fake Christmas tree of it all. Get silly with us on social: FOLLOW THE PODCA...
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, condemn the act of killing bugs outside, and drag the folks who film strangers in public without their consent — seriously, don't do that! Get sill...

What’s up with Delaware?

2024-11-1201:07:12

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 silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimisticatbest Website: pessimisticatbest.com FOLLOW SAMA...

Weaponized Incompetence

2024-11-0501:28:38

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 weaponizing their incompetence. Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimisticatbest Website:...
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 conversation about embracing new hobbies, getting bad sleep, and the curse of the Hyundai Sonata. Get silly with us on social: FOLLOW THE PODCAST ...
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 of cleaning one's makeup brushes, and shame anyone with a cracked iPhone based on what it says about their personality — trust me, it speaks volum...
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 disappointment when we reconvene with our besties after a night out and no one has collected any good tea. Get silly with us on social: FOLLOW THE ...

Concert Etiquette

2024-10-0801:33:13

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 concert tickets without getting scammed. (You know who you are — said with love!) Get silly with us on social: FOLLOW THE PODCAST Instagram: @pe...
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, the horrors of bad plumbing, and the ultimate buzzkill—getting slapped with a parking ticket (or two). Get silly with us on social: FOLLOW THE POD...

Autumn's Rebrand

2024-09-2401:18:43

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 bad sportsmanship. Join in, you know you wanna! Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimis...

The Man Behind the Curtain

2024-09-1701:01:26

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 now infamous apartment tours, the ups and downs of social media, the challenges that come with growing out of friendships, and so much more! Get sil...

Nature's Still Got It

2024-09-1047:42

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 litter. Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimisticatbest Website: pessimisticatbest.com ...
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 emotions. Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimisticatbest Website: pessimisticatbest.com FO...
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 with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimisticatbest Website: pessimisticatbest.com FOLLOW SAMANTHA...

Brat Summer

2024-08-2001:06:34

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 developed pre-frontal cortex (try saying that five times fast!) and, more importantly, to talk mad shit about Glen Powell. Join in, you know you wanna. ...

Standing on Business

2024-08-1301:08:54

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 buildings before we debate over our differing tastes for spooky szn and so much more — join in, the water's fine! Get silly with us on social: FOLLOW T...
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 of my seat when the person next to me on a flight has to use the restroom. Did you miss me? Get silly with us on social: FOLLOW THE PODCAST Instag...

I Love Limes

2024-05-2843:50

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 impending cicada boom, and the horror of discovering you have self-tanner hands. Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimistic...

I Hate White Rabbits

2024-05-2138:11

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 about smoke in the eyes, and argue over whether being late is culturally acceptable, join in! Get silly with us on social: FOLLOW THE PODCAST Ins...

We Contain Multitudes

2024-05-1401:23:53

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 of having a downstairs neighbor, and the harsh reality of it being an election year. Get silly with us on social: FOLLOW THE PODCAST Instagram: ...

Closing Time

2024-05-0701:06:21

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 a deep and intellectual conversation about e-cards, eye doctors, expiration dates, and more. You're seriously not going to want to miss this one ...

Death Penalty

2024-04-3001:21:50

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 in the fun, you know you want to. ;) Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimisticatbest...

Open Campus Lunch

2024-04-2301:07:53

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 pizza and a pink lemonade. None! Join us for a silly little conversation about drunk McDonald's orders, quicksand, walkable cities and so much more. G...

iPad Kids

2024-04-1601:02:08

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 with our hands, because we contain multitudes! Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessim...

With the Works

2024-04-0901:03:17

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 forgive me! Okay, now that we got that out of the way. If you're NOT mad at me, consider joining us for a silly little episode about dogs — big dogs, sm...

Who Invented Nicknames

2024-04-0253:01

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 terror of encountering your local Christian Bible thumper, and the harsh reality of taking an overwhelming amount of supplements and vitamins bef...

Watch This Space!

2024-03-2633:58

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 leaves the house with a chipped mani. Sorry, not sorry! Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @...

We Used to Have Class

2024-03-1939:38

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 little conversation about comfort shows, modern architecture, and boring losers who refuse to shake ass on the dance floor. Get silly with us on s...

Super Fresh

2024-03-1233:25

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 our reverence for animal videos spans generations and stay for my hot take on what it takes to grow out a pixie cut — GUTS. Get silly with us on s...

Choose Your Own Destiny

2024-03-0501:11:30

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 reality TV's latest innovation, The Traitors. You're going to love it, seriously! FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessi...

Ketchup or Mustard

2024-02-2701:10:30

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 shoes. Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimisticatbest Website: pessimisticatbest.com ...

Locked In

2024-02-2047:40

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 with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimisticatbest Website: pessimisticatbest.com FOLLOW SAMANTHA In...
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 you're feeling frisky ;) Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimisticatbest Website: pessim...
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 little ears. This season we're starting a new segment on the pod called, "the good, the bad, and the ugly," and (not to state the obvious, but) durin...

Internet Couple

2023-11-2851:33

Send us a love letter (or hate mail, your choice!) 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 holiday season, if I do say so myself! See you nex...

Who Are We to Say?

2023-11-2101:03:14

Send us a love letter (or hate mail, your choice!) How old were you when you learned to eat vegetables? As a former picky eater, I was admittedly a bit of late bloomer, myself. Magda and I may have grown up in different cities but we were both members of our respective middle school skiing clubs, neither of us can do a cartwheel, and we both decided to take up Gender & Women’s Studies minors sooo, you do the math. Join us for a silly little conversation about health fads, screen time, and...

Midwestern Casserole

2023-11-1401:05:57

Send us a love letter (or hate mail, your choice!) What's your favorite season? If the answer isn't fall, you're wrong, no offense! The weather, the clothes, the variety of soups — I mean seriously, what's not to love? Join us for a little chat about our mutual love for all things autumnal and stay for a run-down of the campiest horror movies and our go-to Thanksgiving side dishes — you're not going to want to miss this wholesome little episode. ;) Get silly with us on social: FOLLOW THE PO...

Hell on Wheels

2023-11-0737:30

Send us a love letter (or hate mail, your choice!) Did you know opting out of Boom Cup could prevent you from contracting coronavirus? That's a W for my non-competitive gals if I've ever heard one! Yes, the rumors are true, James got the vid and then got his job back, and I got to be home for one whole day last week! Anyway, join us for an incredibly slap-happy little conversation that will take you all the way from Las Vegas, Nevada to Nashville, Tennessee, where some guy named Pitt will lov...

Pickle in the Fridge

2023-10-3137:05

Send us a love letter (or hate mail, your choice!) Someone on YouTube commented on one of my recent podcast episodes and said, "Good video and pretty feet," so do with that information what you will! Safe to say I've been wearing socks on the pod ever since. Anyway, your favorite co-host is back, so tune into this week's ep for a breakdown of the difference between spooky movies vs. horror movies and stay to find out why I cried at work. It'll be so fun, I swear! <3 Get silly with us on s...

Two Hours in Calabasas

2023-10-1739:06

Send us a love letter (or hate mail, your choice!) Have you ever traveled to Calabasas and back in a day? Well I have, and it stunk! Picture this—you’re flying Southwest Airlines, you unknowingly choose the seat in between a large party of 40-year old divorcees, you land at LAX and are forced to walk 2 miles to the Uber pick-up spot, you drive to your meeting, black out while pitching ideas to your client, and then head right back to the airport only to find out that your flight home to has b...

Mother Knows Best

2023-10-0301:35:17

Send us a love letter (or hate mail, your choice!) Do you still seek approval from Mom? Don't worry, you're amongst friends! I mean come on, there's truly nothing more validating than an endorsement from your mother, even at the ripe old age of twenty-seven. Alex, Andrew, and I take to the podcast to discuss the challenges of living with food restrictions, the absolute magic of snow days, and the three incredible women single-handedly saving our economy — let's go girls! Get silly with us on...
Send us a love letter (or hate mail, your choice!) Do you believe in astrology? Meg and I are both fire signs entering our Saturn Return, so send us your thoughts and prayers, besties! On this week's ep, we discuss the pros and cons of recreational sports, recount the trauma of running the pacer test in gym class, and share our mutual ick for grown men riding electric scooters in their business casual clothes. We're just a couple of gals on a mission to get out of the house, join in! Get sil...

Funk It Up

2023-09-1901:55:33

Send us a love letter (or hate mail, your choice!) Besties, what do you do when you get into a funk? Do you quit your job? Move to a new city? Guest star on a friend's podcast? All valid options, to be sure! Collin and I take to the pod to chat about when it's appropriate to run away from your problems, what not to order at your favorite fast-casual restaurants, the evolution of bracelet trends in the early 2000s, and so much more. Join us — you know you want to. ;) Get silly with us on soc...

F*ck Ass Bob

2023-09-1201:04:42

Send us a love letter (or hate mail, your choice!) My wonderful friend Clair and I take to the podcast for a philosophical discussion about a few of the very particular life experiences explicitly reserved for twenty-somethings who are post-college, but pre-normal, happy, functioning adult life — including, but certainly not limited to, teaching English in Spain, working in logistics (bonus points if it's for a random trucking company), crying at a music festival, and chopping off all of your...
Send us a love letter (or hate mail, your choice!) I'm not a particularly competitive person and I certainly wasn't gifted with strong hand-eye coordination—and as they say—two wrongs don't make a right. Brit, Cat, and I take to the podcast to share our mutual disdain for competitive sports, dive into our incredibly unlucky losing streaks, and give Cat a proper Chicago send-off before she embarks on her new journey abroad. We're certainly going to miss you, Cat! Catch you across the pond. ;) ...

Only Child Syndrome

2023-08-2957:36

Send us a love letter (or hate mail, your choice!) Fun fact: I once had a classmate give a 5-minute speech about how I'm actually not that big of an asshole despite being an only child — pretty cool right! Ray and I take to the podcast to bond over our "only child syndrome," debate over Drake's silly little habit of adopting new accents, and share our love/hate relationship with self-promotion in the pursuit of our individual creative endeavors. Join in! Get silly with us on social: FOLLOW ...
Send us a love letter (or hate mail, your choice!) Ok be honest, was Twilight your sexual awakening too? I think it goes without saying that we're Team Edward, but the thing about being Team Edward is that we were obviously still hootin' & hollerin' along with everyone else in the theater during that shirtless scene in New Moon. I mean come on, we're only human! My bestie girls and I take to the podcast to dissect the myriad of ways we could become famous, discuss the unsettling CGI tha...
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