Pessimistic at Best

Send us a love letter (or hate mail, your choice!)

Who eats sardines straight from the tin, carries a wad of rubberband-bound singles, and is in “talks” with the Italian government? Depends on who's asking. 

Adam and I take to the podcast to toast to tinned fish, raise a stink about early morning construction, and pour one out for the many folks who were recently denied Italian citizenship thanks to the consulate's ever-cha...

Send us a love letter (or hate mail, your choice!)

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!

Matt and I jump on the podcast to honor our favorite divorce albums, condemn car culture’s grip on society, and reflect on the tragedy of the...

Send us a love letter (or hate mail, your choice!)

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 Wilderness' most infamous waterslide, the Hurricane. Talk about full-body chills!

Colton and I jump on the pod...

Send us a love letter (or hate mail, your choice!)

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 finding an outlet for self-expression, reject the creation of breast milk-flavored ice cream, and criticize the wealthy elite hoardin...

Send us a love letter (or hate mail, your choice!)

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 Latvia, a real place that exists!), dismantle the Digital Menu Industrial Complex™️, and point fingers at people who don't ma...

Send us a love letter (or hate mail, your choice!)

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.

James and I hit the podcast to celebrate mixing metals, call out water bottle fads, and critique public feuds. Join in, you know you...

Send us a love letter (or hate mail, your choice!)

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 take to the podcast to celebrate Chelsea Handler's new book, I'll Have What She's Having, recoil at the thought of receiv...

Send us a love letter (or hate mail, your choice!)

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!

Owen and I take to the podcast to celebrate servers with secret talents, protest loud speakers in public places, and cringe a...

Send us a love letter (or hate mail, your choice!)

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 shows, and complain about men, naturally! Btw, did we ever figure out if Lea Michelle could read? Lmk, seriously.

Get silly with us on ...

Send us a love letter (or hate mail, your choice!)

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 in the pleasure of breakfast with your friends, complain about the reality of women's healthcare, and clap back at people who pick...

Send us a love letter (or hate mail, your choice!)

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 to the podcast to dive into the death of the mainstream, protest our apparent collective dedication to ignoring the human desire to ...

Send us a love letter (or hate mail, your choice!)

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 our favorite onomatopoeias, lament over the humiliation of running to catch the bus, and complain about pants when they inevitably...

Send us a love letter (or hate mail, your choice!)

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 encourage more themed parties, commiserate about just how much it sucks to throw up, and to render our final verdict on t...

Send us a love letter (or hate mail, your choice!)

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 podcast to celebrate the versatility of the fist bump, condemn the act of killing bugs outside, and drag the folks who film strangers...

Send us a love letter (or hate mail, your choice!)

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 traveling for work, and to throw shade at the CTA.

Get silly with us on social:

FOLLOW THE PODCAST
Instagram: @pessimist...

Send us a love letter (or hate mail, your choice!)

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 way to deplane after a flight, and expose people for weaponizing their incompetence.

Get silly with us on social:

FOLL...

Send us a love letter (or hate mail, your choice!)

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's the last thing we do! Join us on the podcast for a conversation about embracing new hobbies, getting bad sleep, and the curse of the H...

Send us a love letter (or hate mail, your choice!)

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 relive the golden age of computer games, lament the hassle of cleaning one's makeup brushes, and shame anyone with a cracked iPhone ba...

Send us a love letter (or hate mail, your choice!)

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 submitting maintenance requests as renters, and our deep disappointment when we reconvene with our besties after a night out and no one has ...