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
Bopping Around for Drinks and Snacks 04.04.2023 46:38
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 34:21
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 39:52
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 2:02:38
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 1:06:35
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 1:10:21
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 58:11
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 1:00:30
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 34:35
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...
A Festivus for the Rest of Us 20.12.2022 32:00
Happy (almost) Festivus! Are you familiar with the holiday? Originally coined by Frank Costanza of Seinfeld, Festivus is a holiday based around the airing of grievances, a practice I’m quite comfortable with myself. Are you familiar with the TikTok trend, “the ick challenge?” Think of Festivus as the original ick challenge and join us as James and I air our grievances or share our icks with one an...
In His Flop Era 13.12.2022 37:42
Did you survive your work holiday party? We made it out alive, but not without taking a few Ls (literally) along the way. To sum it all up, I left my credit card at a bar after making the conscious decision to open a tab (classic) and James swapped jackets with one of my coworkers and lost his wallet in the process. So, naturally, the next morning was spent traipsing around Madison in search of cl...
That Wasn't on My 2022 Bingo Card 06.12.2022 32:15
We’ve been back and forth between Chicago and Madison quite a bit recently. We went home for Thanksgiving, brought the cats, Misho went down the laundry shoot, James shot a deer—it’s been eventful, to say the least! Anyway, we're heading back to Madtown this weekend for my work holiday party, wish us luck, xoxo. Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Fac...
The “R” Word 29.11.2022 1:06:59
Have you heard of the Camino de Santiago? It’s a popular pilgrimage through the north of Spain and my dad just finished his trek. He took the “French Way,” which is roughly the same length as the journey across the state of Wisconsin. Now that you have that perspective, does that make it more or less cool? For me, it’s tough to say, but I can confirm that I would not want to spend 45 days walking...
Susan’s Applehole 22.11.2022 1:04:35
Coworkers by day, Daycatcher groupies by night—we’re just a couple of girls slaying the social media game before pounding a respectable amount of Twisted Teas™ at a basement show and if that’s not your vibe, we don’t want it, sister. Ginny was my first hire at work and now she’s stuck with me forever! Join us for a conversation about surprises, long-distance moves, Ginny’s first snowfall as a Wisc...
Do You Think of Me Differently Now That I Have a Ring Light? 15.11.2022 38:36
The rumors are true—I bought a ring light. Which officially makes me the worst and most famous person that you know. What you decide to do with that information is frankly none of my business. In the meantime, follow me on TikTok, xoxo. What else have you missed? Let’s see—James had his first Chicago show, I lost my credit card, and I’ve officially started beef with our neighbor who somehow manage...
Fight or Flight 08.11.2022 33:31
Serving up my second public apology on a silver platter, honey! I’m genuinely so sorry for going completely MIA for a full three weeks. I had two back-to-back trips (because I’m rich) and am truly terrible at planning ahead but I’m back and ready to bitch about my least favorite airline, brag about my new iPad, totally rock your world, etc. Get silly with us on social: FOLLOW THE PODCAST Instagram...
A Crazy Amount of Squash 11.10.2022 34:20
James released an album (Playhead, out everywhere, xoxo!) and I asked him if he wanted to be on the podcast to promote it like a *real* guest and he laughed in my face! Anyway, join us for a conversation about tunes, tummy aches, and tons of squash if you’re into that sort of thing. Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pessimisticatbest Website:...
Camp Girls Who Can’t Swim 04.10.2022 1:01:06
Were you a camp kid? Typically, most of us fall on one side of the fence, but then there are those of us who landed somewhere in between, went to camp, became obsessed with pop culture, and eventually started podcasts rooted in pessimism—just us? Oops! Anyway, meet my internet-friend-turned-real-life-bestie and learn more about life in Toronto, the reality of the dark web (AKA Reddit), how to play...
Living in Abundance 27.09.2022 1:14:08
We’re giving rich, we’re giving luxury, we’re giving opulence, honey! Jake, my former intern turned work bestie, also just moved to the Windy City™, and to say we’re thriving would be a massive understatement. Is our rent too high? Duh. Are our Ubers outrageously expensive? Obviously. But we’re rich in experiences, baby—and that's what counts. We’re just a couple of city gals living in absolu...
Chronically Online 20.09.2022 1:30:36
From the unanswered question surrounding Lea Michele’s ability to read to the Don’t Worry Darling red carpet drama to the Queen’s death (RIP in peace), it was quite the week—especially for those of us who simply can’t pry our eyeballs away from the internet. Sara and I are social media managers by day and pop-culture connoisseurs by night. We’re just a couple of gals with an incurable disease in w...
Running My Silly Little Errands 13.09.2022 47:19
Scheduling a dentist appointment to cement myself as a Chicago resident, wbu? Seriously though, there’s nothing quite like running undesirable errands to make you feel established in a new city. A trip to Milan Laser is next—time to fill that calendar, honey! P.S. Justice for Tasha, Love Island Season 8. xx Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimisticatbest Facebook: @pe...
Crying in Public 06.09.2022 38:57
We’re BACK! Did you miss us? Because we sure missed you! It’s been eight long weeks, but to recap everything you may have missed—we made the big move to Chicago, one of us has picked up a new habit of crying in public, and the other’s been dabbling in AMAs on Instagram. Anyway, it’s great to be back! Season four, here we come. ;* Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimis...
Being More Intentional or Whatever 28.06.2022 41:05
And that’s a wrap on season 3! Join us for a mid-year intentions check-in where we discuss how little I’ve worked on being better at spending time alone and how much more “intentional” James has been since setting his new year's intention as being more intentional. Confused? Same! Hope to figure it all out once I turn 26—see you in August, xx. Get silly with us on social: FOLLOW THE PODCAST I...
Hot People with Tummy Aches 21.06.2022 47:22
James and I just got back from the PNW, are you jealous? We thought so! We took a trip up to Seattle and Vancouver to visit friends and family and had a blast, but unfortunately, we also had tummy aches the entire time—you win some, you lose some! Enjoy this little trip recap and see if you can guess what made our tummies hurt! xx Get silly with us on social: FOLLOW THE PODCAST Instagram: @pessimi...
Computer Games Raised Us 07.06.2022 2:03:09
Did you grow up playing computer games? Did you base your friendships on whoever had the best internet connection? Did your parents take money out of your allowance so that you could be a member of both Club Penguin and RuneScape? Well, you're in luck, because Annie and I can very much relate! Tune in to this week's pod to listen to us reminisce on our early friendship, divulge our elem...
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