Sam Georgson

Pessimistic at Best

Comedy EN ↓ 180 episodes

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...

Author

Sam Georgson

Category

Comedy

Podcast website

www.pessimisticatbest.com

Latest episode

May 12, 2026

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Episodes

This One's for My Non-Sporty Girls 05.09.2023

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

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

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

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

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

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

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

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

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

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

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

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

 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

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

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

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...

Bopping Around for Drinks and Snacks 04.04.2023

Not to brag, but I recently had a Tweet go viral (upwards of 2+ likes) about how vacation is really just about bopping around for drinks and snacks., and honestly? I stand by that. James and I just got back from London, the literal trip of a lifetime, so naturally I wrote up a pros and cons list for the recap. Let's dive in, shall we? Get silly with us on social: FOLLOW THE PODCAST Instagram:...

The Girl Who Never Shuts Up About Study Abroad 28.03.2023

It's me, hi, I'm the problem, it's me! James and I decided to take a ten year anniversary trip across the pond and I may or may not have gotten us an Airbnb as close to my old dorm as humanly possible — we're reliving the glory days, baby! Goals for the trip include convincing at least one person that I'm British and maintaining a healthy gut microbiome throughout our stay...

Drunk on Spring and Sudafed 21.03.2023

I sold my car and bought a Pitchfork ticket — spring has sprung and love is in the air! Spring is an incredibly intoxicating season, isn't it? Especially when you live in a winter hellscape like we do here in the midwest, but as they say, you have to experience the lows to appreciate the highs, am I right ladies? Join us for a conversation about attempting to sell your car online, cleaning ou...

Number Two 14.03.2023

This one is for my IBS girlies! This is probably the first time we've openly discussed excrement on the pod, and frankly, it may also be the last! But in the wise words of Tarō Gomi — everyone poops. So, with that said,  join us for a liberating conversation about bodily fluids, new friends, light-up shoes, and more! Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbes...

Justice for Anne Hathaway 07.03.2023

Anne Hathaway is in her bag and where are you? We, as a society, owe Anne and all of the try-hard girlies and cringey queens a sincere apology. Allow women to be cringe! It’s their god-given right. So all of that is to say, if you’re team Anne, join us for a conversation about following celebrities on social media, cutting your bangs right before leaving the house, and so much more! You know you w...

Somebody Call the Locksmith 28.02.2023

Life hack: Lock a stranger out of their own home in order to force them into a life-long friendship! That's how Evan and I became besties and the rest is literally history. Tune in for the deets on our friendship origin story and stay for a lovely little conversation about our mutual love of thrifting, our shared struggle to find our respective TikTok personas, the delicate art of feng shui,...

Girls Can Have a Little Hangxiety as a Treat 21.02.2023

Welcome to the hangover episode where Sophia and I discuss the politics of bar-time karaoke and share our go-to hangover prevention methods before embracing our hangxiety and freaking out over our impending Saturn return. Pop some Advil and come along for the ride if you’re feeling brave, xoxo. Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimisticatbe...

We Stand with Renters 14.02.2023

Have you heard about the guy who traded a paperclip for a house? Well how about this for news —  Jake and I are both renters in Chicago, and although we may not have a house like Paperclip Guy, we do have beautiful relationships with our maintenance workers and we don’t have to shovel snow like the freaks with mortgages. Join us for a conversation about holidays, home decor, concussions, and more!...

Inviting Strangers Over for Dinner 07.02.2023

We’re back, we paid off our couch, and we’re onto season 5! Join us as we recap our break and catch you up to speed on all of the adult things we’ve been doing recently, including but not limited to making the active choice to spend less time on our phones, opening a new line of credit, going to a friend’s wedding, and inviting strangers over to our house for a sit-down dinner. Incredible things c...

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