Sam Georgson
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 t he 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 lie...
Be sure to visit the podcast's website and support the creator: www.pessimisticatbest.com
Author
Sam Georgson
Category
Podcast website
Latest episode
Oct 20, 2026
Where to listen?
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Episodes
Who Are We to Say? 21.11.2023 1:03:14
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 co...
Midwestern Casserole 14.11.2023 1:05:57
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 wh...
Hell on Wheels 07.11.2023 37:30
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...
Pickle in the Fridge 31.10.2023 37:05
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 crie...
Two Hours in Calabasas 17.10.2023 39:06
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 o...
Mother Knows Best 03.10.2023 1:35:17
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-handed...
Girls Just Want to Play Outside 26.09.2023 1:36:33
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...
Funk It Up 19.09.2023 1:55:33
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...
F*ck Ass Bob 12.09.2023 1:04:42
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), cryin...
This One's for My Non-Sporty Girls 05.09.2023 1:35:14
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'r...
Only Child Syndrome 29.08.2023 57:36
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 c...
Where the Hell Have You Been, Loca? 22.08.2023 1:26:02
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 myria...
Irrational Fear of Teens 15.08.2023 1:29:58
Do you dodge teenagers like the plague? Do you cross the street to avoid crossing their path? You may have ephebiphobia or an irrational fear of teens, and let it be known that you're amongst friends. Sarah and I take to the podcast to share our mutual fear of TikTok's target demographic and bond over our experiences growing up in the catholic church before diving into life as a grief th...
Feeling Strong and Brave 08.08.2023 51:05
Season 6 is here at long last! Let us catch you up on everything that's happened since we last spoke, from vowing never to travel with our cats again to waking up with a stranger in our bed to Lizzo getting canceled for body-shaming her backup dancers. It's been an eventful few weeks, to say the least, let's dive in. ;) Get silly with us on social: FOLLOW THE PODCAST Instagram: @pes...
Just a Girl and Her Dental Fillings 27.06.2023 46:25
One hundred episodes in and we're feeling fine! James and I take to the podcast to celebrate with a riveting discussion about our stance on hot tubs, Chicago's breakfast spots, and the potentially life-altering decision to say goodbye to Eucerin forever, sounds fun, right? Join in! P.S. To whom it may concern, I recently discovered that I had two cavities and got my first-ever dental fil...
Sore Loser 20.06.2023 52:59
If it's one thing about me, I'm not competitive, but I am a sore loser. James and I just got back from a trip to Milwaukee to celebrate a friend's birthday and we played an absolutely ridiculous amount of card games, got in a fight about whether or not to go to Summerfest, ate copious amounts of kettle corn, then, ironically won a ticket to Summerfest — life is a silly little game,...
24K Magic in the Air 13.06.2023 1:01:35
The theme is rhinestones and denim, honey! Friend of the pod, returning guest, the light of my life, and fire of my loins, Grace Ferolo joins me back on the podcast to recap her recent trip out to Sin City to see the man, the myth, the legend, Bruno Mars, before we dive into the plight of the angry woman, the blessing & the curse of having a busy schedule, and the quest for love in all forms....
Naked Bike Ride 06.06.2023 46:54
Personally, I've never had the urge to get butt naked and take my bicycle for a spin through the city streets, but who am I to yuck somebody else's yum! Join us on the podcast for a lovely little recap of James' birthday weekend and stay for my newfound favorite cure for the hiccups, James' issue with divvy-bike sanitation practices, our pitch for the drink of the summer, and m...
America's Favorite Pastime 30.05.2023 44:53
There's nothing more patriotic than celebrating Memorial Day Weekend with a Vienna hotdog and a Miller Lite at the stadium, am I right ladies? James and I take to the podcast to discuss my googling "grills for beginners" ahead of our trip to Home Depot, our mutual distaste for sandals, and more! Gear up for a taste of the American spirit, if you know what I mean, xoxo. Get silly wit...
Barefoot-Boy Summer 23.05.2023 1:47:19
Barefoot-boy summer is upon us, the sun is shining, and for better or for worse, the toes are OUT. Kyle and I take to the podcast to reminisce on our first swear words (or cuss words for you Texans), share our favorite phone games, and swap foot fetish stories, join us if you dare. ;) Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimisticatbest Website...
It's Not a Proper Doctor's Office Unless There's a Fish Tank 16.05.2023 51:55
When was the last time you had a hand cramp? Well, I got one writing the notes for this episode, so it must be good! James and I take to the podcast to discuss the odd marketing tactics of a quirky local establishment here in Logan Square called the Friendship Chinese Restaurant before diving into my unhealthy obsession with Facebook Marketplace and my stance on Doctor's offices without fish...
Slap a Label on Me 09.05.2023 51:55
If it's one thing about me, it's that I love a personality quiz. Categorize me, put me in a box, slap a label on me, I don't mind! I just got back from my all-company summit in which I found out that I'm a "collaborator" within the Predictive Index. I actually felt like I learned a lot about myself — and all after answering two measly questions, imagine! Anyway, join...
Money Does Buy Happiness 25.04.2023 1:11:11
Rich people ruin everything but also like — gimme some, you know? Money absolutely does buy happiness and whoever says otherwise is lying to your literal face and should not be trusted, got it? Anyway, join us for a heated debate about the importance of adding to your savings account, and stay for a riveting conversation about voodoo dolls & ouija boards, closeted nerds, men in heels, and more...
Drive Your Tractor to School Day 18.04.2023 1:08:28
Today the Kedzie Kids™ take to the pod to tackle an important question — 'Drive Your Tractor to School Day' — urban myth or rural fact? Join us for a riveting conversation about middle school bullies, ripped pants, and life on the dairy farm — and stay for a charming little anecdote about the time that I almost threw up when it was my turn to milk the cow during a school field trip. Get...
TV Is for Intellectuals 11.04.2023 1:06:53
At this time, I'd like to give a shoutout to British Airways via American Airlines for reconnecting me with Abby Mackinnon on the way to the most magical place on earth — London, of course! I can genuinely say that I'm so incredibly happy our departing flight got moved up a full 3 hours and that our connection was moved all way from JFK to CLT because had that not been the case, I wouldn...
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