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 dares to ask the question—have we tried listening to women?
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!
Episodes
160 episodes
Sexy Unique Restaurant
It’s important to remember that the SUR experience has little to do with the food. Its true specialties lie in campy ambiance, overpriced cocktails, and the chance to share a room with some of reality TV’s messiest players—pure bliss!Ma...
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1:10:23
The Waterpark Capital of the World
Picture this: You're freshly thirteen, you've got your brand new Ocean Pacific swimsuit on, and you're patiently making your way up the wooden staircase with your tube in hand. What's waiting for you at the top, you ask? None other than the Wil...
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1:26:25
Wrestling Is the Straight Man’s Drag
Name something more c*nty than a giant chiseled man with a spray tan and platinum blonde blowout strutting to the ring in a bedazzled outfit to the tune of "Real American"—you can't!Rohan and I take to the podcast to celebrate grown men ...
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1:00:40
Just Scan the QR Code on the Table
If I have to use my own cellphone to pull up the menu at the restaurant, I'm clocking in because I work here now. I said what I said!James and I return to the podcast to celebrate Flow's Academy Award for Best Animated Feature (s/o to L...
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46:52
Feeling Insecure About My Water Bottle
I recently found myself feeling insecure about my Hydro during a Zoom call full of Stanleys and decided enough is enough! Screw your trendy water bottle! Unless you're still chewing on your Camelbak straw, like seriously, it's time to move on.<...
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39:55
Leaving It All on the Field
Picture this: The year is 2025 and you're making the active choice to jump back on the reading train after it dawns on you that you've forgotten how to do anything besides watch TV. Sound familiar? If so, you're safe here!Grace and I tak...
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1:22:33
Seafood Boil Mukbang
Have you ever been out to eat when your waiter suddenly goes missing, only to reappear on stage, mic in hand, bringing down the house? It's like, sure you wanted another martini, but ultimately you're happy they're having their moment!O...
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1:04:16
Gleek Hive Rise Up
Were you normal, or were you spending your iTunes gift cards on Glee covers? Don't worry, you're amongst friends! Donnie and I take to the podcast to celebrate authenticity, stress over our favorite strategy-based reality TV game sh...
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1:11:51
Breakfast Is Thrust Upon You
Brunch is something you plan in advance. It's an event you prepare for. Heck, you might even put on a cute outfit! Breakfast, on the other hand, is thrust upon you (whether you like it or not!)Luke and I take to the podcast to rejoice i...
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1:31:28
Death of the Mainstream
Everyone can be someone and anything can be cool — and isn't that beautiful? Sure, there will always be pop stars with seismic fanbases like Taylor Swift and Beyoncé, but the "mainstream" is over, you heard it here first!James and I take...
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1:03:49
When Your Pants Get a Little Loose at the Knees
We're back, babies! And ever so grateful to be back in your ears each week. We missed you terribly — what a long two months it has truly been. Much to catch up on, so let's take it from the top!James and I take to the podcast to share o...
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46:00
You Seem Tired
Friendly reminder that the absolute worst thing you can do is tell someone they seem tired, it never goes over well. Instead, you could try, "You look like shit," or "What the hell is your problem." This week James and I take to the podcast to ...
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31:15
Becoming a Better Person
Great news team, becoming a better person is actually incredibly easy! Follow our 5-step process and you'll surely go straight to heaven or be reincarnated as something really cool or whatever. In this week's episode, James and I take to the po...
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40:16
What’s up with Delaware?
Have you ever been to the state of Delaware? Because me neither, and I have no designs on visiting! Devonte and I take to the podcast to celebrate finding fulfillment in our respective careers and shared community, to burst the bubble that is t...
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1:07:12
Weaponized Incompetence
Playing dumb is all fun and games until you're on the receiving end of such behavior — we said what we said! Aidan and I take to the podcast to sing the praises of our favorite fast-food chain (Taco Bell, duh!), deliberate over the appropriate ...
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1:28:38
The Quest to Become a Morning Person
Are you buying into the propaganda that morning people are more productive? Because we’ve sold our souls and signed on the dotted line. Manu and I are just a couple of night owls on the quest to become early risers and get that damn worm if it'...
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1:18:46
What Your Cracked iPhone Says About You
If you listen to this episode I'm sorry and if you make it all the way to the end something is literally wrong with you! Truly rubbing my last two brain cells together for this one, enter at your own risk! James and I take to the podcast to rel...
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50:53
We're Not Friends We're Business Partners
We're starting a support group for people who have had to execute a Facebook Marketplace pickup while viciously hungover—do you want in? Luke and I take to the podcast this week to chat about our favorite micro-influencers, our aversion to subm...
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1:11:29
Concert Etiquette
If it's one thing about us, it's that we're going to buy tickets to the concert! Annie and I take to the podcast to share in our love for being "woo" girls at our favorite live shows, to bitch about music venues that don't have water stations, ...
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1:33:13
9 Beers, 9 Hotdogs, 9 Innings
How many hotdogs could you reasonably consume in a 2.5-hour sitting? The 9x9x9 challenge has officially met its match, and I have the absolute pleasure of hosting our fearless champion on this week's podcast! Neil and I take to the pod to chat ...
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1:26:04
Autumn's Rebrand
Is it just us, or do all Midwestern dads have the same undeniable penchant for building elaborate underwater ecosystems within the home? What’s the story there? This week on the podcast Grace and I share our affinity for Autumn's rebrand, our l...
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1:18:43
The Man Behind the Curtain
If you're chemically addicted to watching Chicago apartment tours on TikTok, this episode is for you! Get to know the man behind the curtain (or camera), from his least favorite household chore to his go-to Chipotle order. Dean and I take to th...
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1:01:26
Nature's Still Got It
You know you've been spending too much time indoors when you go outside and think to yourself, man it rocks out here!! James and I take to the podcast to chat about the benefits of being curious, the worst smells at the Logan Square Farmer's Ma...
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47:42