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
149 episodes
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
This Year We're Acting Hot
Now, I'm not here to tell you to fake it until you make it, but sometimes the key to being hot is simply acting hot!!! Pat and I take to the pod this week to share our mutual love of Google Calendar, divulge our early interest in retir...
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59:14
Not Going to Let a Man Tell Me What to Do
If it's one thing about us, it's that we're never going to let a man tell us what to do. Dante and I take to the podcast to sing the praises of this summer's pop girlies, lament the horrors of moving, and ruminate over the audacity of ...
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1:13:10
Brat Summer
Did you know that humans cement their taste in music in their late twenties? Feeling incredibly blessed to live during a time in which my Saturn Return overlaps with Brat Summer — formative years to say the least! Mickey and I take to the podca...
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1:06:34
Standing on Business
The Olympics had us singing "Party in the USA" just before the Chicago Air and Water Show came along and knocked the red, white, and blue right out of us again — because that's where we simply must stand on business! Ciara and I take to the pod...
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1:08:54
For the Love of the Game
We're baaaack, and much to everyone's dismay, we're better than ever! Join us for our season kick-off where James and I take to the pod to share in our love for swimming and our distaste for servers that overcompensate, and stay for an impassio...
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47:38
I Love Limes
Is there anything better than seeing how the other half lives? If you enjoy treating yourself to celebrity home tours or listening to Dakota Johnson ramble on about false fruit obsessions, this episode is for you! Join us for a silly little con...
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43:50
I Hate White Rabbits
Sitting around the campfire is all fun and games until you become the chosen one and suddenly you're blind and both of your lungs collapse. Not to mention the lingering smell that adheres to everything you own — 'tis the season! James and I jum...
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38:11
We Contain Multitudes
Did you have a Christian phase? Have you also been arrested? I'm not saying there's a correlation, but let's look at the facts. Kyle and I self-identify as total sweethearts, but previously we were singing hymns and doing time. Join us for an...
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1:23:53
Closing Time
Picture this: It's 1:30 am, the lights come on, 'Closing Time' starts playing over the speakers, the bartenders have turned on you and there are two big burly guys telling you that you can't wait for your Uber inside. Is there anything worse? <...
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1:06:21
Death Penalty
Do you suffer from road rage or are you medicated? As a proud passenger princess myself, I typically abstain — but I understand the urge, driving is hard! Let it out, bestie! Dylan and I take to the pod to grumble about physical labor and publi...
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1:21:50
Open Campus Lunch
Did your high school have an open campus lunch or were you one of the unlucky ones? I hate to break it to you, but there is truly no experience that could compare to piling seven deep in a friend's car and zipping across the street to the mall ...
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1:07:53