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 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!

Podcasting since 2020 • 179 episodes

Pessimistic at Best

Latest Episodes

We're Off the Stuff

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,...

May 05, 2026 • 1:20:29

We've Been to the Year 3000

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 th...

April 28, 2026 • 56:35

It's Really Hard to Be Alive

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 episo...

April 21, 2026 • 1:15:10

Can I Interest You in a Glass of Milk?

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.<...

April 14, 2026 • 1:26:16

U-Haul

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 t...

April 07, 2026 • 1:27:53

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