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PODCAST

Pessimistic at Best

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 operates on the belief that no complaint is too small.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

comedy comedy interviews

All Episodes

89:41

The Art of Escaping the Charity Solicitor

Pessimistic at Best ·

2026/10/06

A woman in a vest clutching a clipboard just caught your eye from across the street and it's too late to turn around, wyd? Sarah and I take to the podcast to discuss getaway strategies for escaping the ever-annoying fundraising canvassers (no offense! we support the cause, we're just on our way to brunch!)Then we dive into the good, the bad, and the ugly: embracing the change of the seasons with open arms, the shame of having a high screen-time, and rewatching Glee in an unironic

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83:21

Accidentally Sending a Risky Text to Your Boss

Pessimistic at Best ·

2026/09/29

Have you ever fired off a text to the wrong person? Was it an (accidentally) explicit text that you sent straight to your boss? Were you surprised to be offered a promotion afterwards? We might not all be this lucky, but Kate sure was — we have a good laugh about this one!Then we get into the good, the bad, and the ugly: maintaining a sense of childlike wonder, the meta glasses takeover, and having the audacity to litter.THERE'S MORE WHERE THAT CAME FROM:SUBSCRIBE TO THE NEWSLETTER:Substack:

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83:02

Making Out at the Party

Pessimistic at Best ·

2026/09/22

What's your stance on public displays of affection? Are you open to a steamy hookup at the bar? As someone with a long-term partner, I'm typically abstaining from engaging in PDA myself (sorry, we can do that at home!), but Evan and I agree that catching a pair of strangers locking lips is the sign of a good party. Then we dive into the good, the bad, and the ugly: betting on yourself, feeling like a cog in the corporate machine, and the lack of originality sweeping the culture —

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61:02

Using Your Calculator to Determine the Tip

Pessimistic at Best ·

2026/09/15

If you're good at math, you probably have no original opinions. Anyone can solve a problem that someone else solved first, but not everyone can develop a totally and completely unique point of view. Some of us were actually born interesting! Adam and I agree that it's actually perfectly fine and completely normal to pull out your calculator to confirm the tip on the bar tab.Then we get into the good, the bad, and the ugly: moving in with a partner and building a space together, moving in

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75:37

Peak Luxury is Going Out for Breakfast

Pessimistic at Best ·

2026/09/08

Name something more luxurious than dining out for breakfast, we’ll wait! A dinner reservation is (of course) classic but ultimately unoriginal, lunch is mostly giving fast-casual corporate escape—but breakfast? Aris and I wholeheartedly agree that breakfast is where it’s at. Then it’s time for the good, the bad, and the ugly: having access to a bathtub, people who don’t share the sidewalk, and the general concept of chewing gum. THERE'S MORE WHERE THAT CAME FROM:SUBSCRIBE TO THE

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49:43

Life is Mostly About Landing Tricks

Pessimistic at Best ·

2026/09/01

Do you do all of your own stunts? For some (James), life is mostly about hitting sequences and mastering combos; for others (me), putting down moves plays a less significant role. On this week's episode, James and I dissect the importance of landing tricks.Then we get into the good, the bad, and the ugly: yo-yoing as a new favorite pastime (re: tricks!), the horrors of a failed sneeze, and the pick-mes riding around on their double-decker bikes.THERE'S MORE WHERE THAT CAME FROM:SUBSCRIBE

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42:01

State Sanctioned Diabetes

Pessimistic at Best ·

2026/08/24

Sometimes your cat will be diagnosed with diabetes because he was addicted to getting UTIs so the emergency vet had to inject him with steroids that cause the pancreas to act up which will ultimately cost you ten thousand dollars!!! This episode is basically a PSA to get the pet insurance btw!!!Then we dive into The Good, The Bad & The Ugly: stone fruit season, taking the decorations down after the party, and people who are judgmental about doing AC on and windows open at the same time (live a

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81:44

Finding Our Zen or Whatever

Pessimistic at Best ·

2026/05/12

The secret to finding your zen? Perhaps it's going off the grid to fish on some remote lake in the middle of Canada, cracking a cold one and watching the storms roll through, or picking off your moles one by one — who am I to judge? Drue and I take to the podcast to workshop the concept of relaxation, results pending. Then it's time for The Good, The Bad & The Ugly: thunderstorm season, the quiet death of the multi-instrument music store, and why milk is the one drink that turns people

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80:29

We're Off the Stuff

Pessimistic at Best ·

2026/05/05

You know what's chic? Cutting back, scaling down, doing sort of a less is more moment. In reference to what exactly? Well, anything that's no longer serving you, of course! On this week's episode, Jeremy and I dive into what we're saying no to, including carbonated beverages, aluminum-free deodorant, and then some.Then it's time for The Good, The Bad & The Ugly: When the function involves karaoke, the overabundance of Santal 33, and men who forget how good they've

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56:35

We've Been to the Year 3000

Pessimistic at Best ·

2026/04/28

POV: It's 2006, the Jonas Brothers have just released their debut album, It's About Time, and you briefly leave your body. Caroline and I get into her music origin story, her earliest fandoms, and how that eventually led to building the Chicago Show Calendar.Then we get into the Good, the Bad, and the Ugly: Ditching Spotify and starting fresh on Qobuz, the way people undervalue small businesses, and music industry PR literacy ft. the Geese psyop discourse.FOLLOW CAROLINE & CHICAGO SHOW

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75:10

It's Really Hard to Be Alive

Pessimistic at Best ·

2026/04/21

Have you ever had to do a few laps around Agora Market before working up the courage to ask the guy behind the deli counter for a pound of pork chorizo? Because for some of us, that's just a Thursday! Martina and I spend this week's episode mostly agreeing that it's actually really hard to be alive!!!Then we dive into the Good, the Bad, and the Ugly: writing your affirmations by hand, working through an eBay addiction, and when the deodorant smell is too obvious.Support the

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86:16

Can I Interest You in a Glass of Milk?

Pessimistic at Best ·

2026/04/14

Milk with dinner is a Midwestern birthright, and the internet has a lot of feelings about it. Whether you've kept the faith, developed a tragic intolerance, or just quietly renounced your heritage, Sophia and I weigh in on this week's episode.Then it's time for The Good, The Bad & The Ugly: the year of the Fire Horse, wedding gift culture, and people (read: losers) who don't dress up for themed parties.Support the showTHERE'S MORE WHERE THAT CAME FROM: FOLLOW THE

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87:53

U-Haul

Pessimistic at Best ·

2026/04/07

Send us a love letter (or hate mail, your choice!)Listen, we're going to let you in on a little secret — if you ever find yourself stuck somewhere and there are no rental cars available, you're going to get your ass over to the nearest U-Haul and take it from there, okay? Donnie and I hop on the podcast to swap survivor skills and Survivor 50 hot takes.Then we dive into the Good, the Bad, and the Ugly: Embracing your 30s with open arms, airline horror stories, and toxic masculinity running

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77:48

A New Bombshell Has Entered the Villa

Pessimistic at Best ·

2026/03/31

Send us a love letter (or hate mail, your choice!)POV: I interrupt your sunbathing to ask if I can pull you for a chat, but I'm a sexy banana named Benanito, wyd? Greg and I take to the podcast to dissect the AI-generated, fruit-themed Love Island mini-series that has taken TikTok by storm.Then we dive into The Good, The Bad & The Ugly: recycling old trends, DJ remixes at bars, and the delivery robots terrorizing the streets of Chicago.Get silly with us on social:FOLLOW THE

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89:35

To Be Cringe Is to Be Free

Pessimistic at Best ·

2026/03/24

Send us a love letter (or hate mail, your choice!)Unfortunately whoever said, "If a thing is worth doing, it is worth doing badly" was onto something. Post your first attempt at a french mani to main, publish the scripted podcast episode you recorded out of your studio apartment, to be cringe is to be free! Alex and I jump on the podcast to talk about Doing the Thing™️, whatever that thing may be. Then it's time for The Good, The Bad & The Ugly: embracing creative collaborations,

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40:52

Mint and Chocolate

Pessimistic at Best ·

2026/03/17

Send us a love letter (or hate mail, your choice!)When it comes to sweets, what's your preferred flavor profile? There is a right and wrong answer, btw! If you gravitate toward fruity desserts, you're officially in the doghouse. I don't make the rules! If, like me, you yearn for rich, chocolatey confections, congratulations, you've been marked safe! James and I take to the podcast to dissect his disturbing take on all things sweet.Then it's time for The Good, The Bad &

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71:36

Reality TV Pilled

Pessimistic at Best ·

2026/03/10

Send us a love letter (or hate mail, your choice!)Who needs fictionalized drama when you have the service industry? There's no group more ripe with scandal than the front-of-house staff at your favorite local haunt. Sophia and I take to the podcast to celebrate reality TV's greatest hits, including the likes of Vanderpump Rules and Southern Hospitality. Then it's time for The Good, The Bad & The Ugly: stealing from big box grocery stores, letting your intrusive thoughts get the

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88:09

The Best Places to Cry on Campus

Pessimistic at Best ·

2026/03/03

Send us a love letter (or hate mail, your choice!)College was a fever dream, a bunch of kids living in a pretend world, cosplaying as adults with meal plans, and it was awesome!!! Mickey and I jump on the podcast to chat about our freshman year floor (s/o Sellery 7A), navigating co-ed living and communal bathrooms, and the best places to cry on campus. Then it’s time for The Good, The Bad & The Ugly: getting your alderman involved, construction companies that have the audacity to wake you up on

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65:26

A Pink Lamborghini

Pessimistic at Best ·

2026/02/24

Send us a love letter (or hate mail, your choice!)Are you ready to level up your dating game? Looking to impress some lucky lady? The Rizzler says the key to winning her heart is actually quite simple, head to your local mall and buy her a pink Lamborghini, duh!!!Conor and I take to the podcast to celebrate his 30th with a little help from the Rizzler himself, file a formal complaint about the Mariano's on Chicago Avenue for its complete disregard for the customer experience, and surrender to

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54:11

Stuff vs. Things

Pessimistic at Best ·

2026/02/17

Send us a love letter (or hate mail, your choice!)What constitutes stuff vs. things? Easy, boys like stuff, girls like things, and a dream is a wish the heart makes, next question! Meghan and I take to the podcast to settle the stuff vs. things debate, defend the typo, survive a smelly Uber, and drag the completely vibeless CVS on Chicago Ave. Join in, you know you wanna!Get silly with us on social:FOLLOW THE PODCASTInstagram: @pessimisticatbestFacebook: @pessimisticatbestWebsite:

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