Cup to Cup | The Comedy Podcast
Enjoy this naughty blend of hilarious Florida man adventures, dad jokes and a dash of ‘Irresistible’ charm in this sexy adult comedy podcast
Episodes
July 10, 2025 • 92 mins
We start this one off hot—Kevin’s having a meltdown, Jason’s picking fights, and SOMEONE is locked out of their own damn computer. Meanwhile, Chris is pretending to be organized while secretly rigging the the BIG BOARD. We dive into the shady world of dealership oil changes, how to blow $10 million (with zero tax planning), and what exactly a meth-fueled Oregon man was doing when the cops showed up (spoiler: it’s NSFW). There’s als...
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July 3, 2025 • 106 mins
This week’s episode starts like a normal podcast... and then quickly nosedives into peak chaos. The guys dive into hot takes, donation drama, and whether Kevin is a “supreme leader” or just loud. One minute we're talking Pride Month merch, the next we’re debating Twitch follow etiquette, and somewhere in between, someone gets roasted for drinking alone. Again. There’s arguing, there’s laughter, and there’s at least one moment where...
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July 1, 2025 • 77 mins
Its sports... MLB: -Fantasy Studs & Duds -Better chance to win the HR Derby: Acuna or Raleigh? NFL: -Which 2024 Playoff Team will miss the playoffs? 🏈 American Football Conference (AFC) Kansas City Chiefs – AFC West Champions (15‑2) Buffalo Bills – AFC East Champions (13‑4) Baltimore Ravens – AFC North Champions (12‑5) Houston Texans – AFC South Champions (10‑7) Los Angeles Chargers – Wild Card (11‑6) Pittsburgh ...
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June 26, 2025 • 90 mins
t’s been a minute but the full squad is back together (including Jason from Texas!) We open up the episode talking about a good song if you are caught in a bar fight. Florida Man takes us to Gulf Breeze involving a dude and some cooking oil. Chris has the latest Random Twitter Finds involving C items. Kevin has his weekly Dad Tip and Jose holds us accountable with WWFU. Chase wraps up the episode with Trivia for the Big Board. S...
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June 18, 2025 • 81 mins
We still have members of the crew missing as it’s a trio squad for this episode. They open up the episode talking about more traumatizing than they realize. Florida Man takes us to Kentucky involving “Cowboy Cody”. Kevin has the latest Picture Time for us with some help from his new best friend. Kevin also has his weekly Dad Tip and Jose is back for WWFU. Chris isn’t here but does have a Would You Rather and Chase has Spot the Fa...
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June 17, 2025 • 60 mins
NFL: -Give me a reason why your NFL team will win the Super Bowl this year and give me one reason why they won’t win it this year. MLB: -Fantasy Studs & Duds -Who would you rather have for a full career: Derek Jeter or Chipper Jones? FSU: -College Gameday not coming to FSU for Corso’s final show; Which game should he be back to be honored for? -Is this the angriest the FSU fan base has ever been?
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June 11, 2025 • 69 mins
Some of the crew is still dragging after the Big 300 so it’s only a trio squad tonight. We open up the episode talking about which cars are driven by a**holes. Florida Man actually takes us back to Delray Beach. Chris has the latest Movie Time showing Chase’s obsession with Natalie Portman. Kevin has his weekly Dad Tip and Chris has the latest Random Twitter Finds mixing hot and cold. Mayor Andy steps in this week for WWFU from the...
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June 10, 2025 • 62 mins
ITS SPORTS....WE DONT REALLY WANNA TALK ABOUT IT THIS WEEK BUT WE DID. FSU, BRAVES, RODGERS, JAIRE ALEXANDER....EVERYTHING SUCKS!!!
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June 5, 2025 • 170 mins
Whether you started from Episode 1 or just joined us, we love and thank you for the support! A full squad for the special 300th episode. We open up talking about Severance and Florida Man involves yet another theft. Chris has a Would You Rather that maybe the crew actually likes. Chase has some podcast trivia for chances at the Big Board. Chase also has She’s Always Right and Kevin has his usual Dad Tip. Jose does WWFU to remind ...
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May 29, 2025 • 82 mins
It’s only a quad crew this week as Chase decided to go on vacation this week. We opened up this week talking about which beer you would get at a restaurant. Florida Man takes us a minute to understand but it involves some science. Chris has another edition of Blind Rankings involving some popular side items. Kevin is back this week with a new Dad Tip. Jose has the latest WWFU and another solid moment of cringe and Chris has anot...
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May 27, 2025 • 55 mins
Its sports... NFL: -Tush Push lives -Onside Kick Change MLB: --Fantasy Studs & Duds -Could the Rockies be the worst team ever? FSU Update: -Softball loses to TT -FSU Baseball: ACC Tournament -CFB Playoff moving to straight seeding mode Follow us at Cuptocupshow ON ALL SOCIAL (no-spaces) The CTC Onlyfans on FB Visit our site at Cuptocuplife.com (nospaces)
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May 22, 2025 • 69 mins
It’s a quad crew this week as Kevin is dealing with tornadoes and fiber issues. We open up this week talking about what you do when you are really angry. Florida Man takes us to Orlando and no surprise involves the police. Chris has the latest Blind Rankings involving a famous actor. Jose has the latest WWFU with an epic moment of cringe. Chase wraps it up with his version of Name That Show for the Big Board. Special thanks to M...
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May 20, 2025 • 59 mins
Its sports... Guess The Year NFL: -Schedule Release; Is it too early for….. -Brock Purdy got PAID -NFL Playoffs change? MLB: -Fantasy Studs & Duds -Chase continues to KOD the Braves FSU Update: -Baseball vs UNC (ouch) -Softball Regionals Follow us at Cuptocupshow ON ALL SOCIAL (no-spaces)
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May 15, 2025 • 107 mins
It’s the full squad back together this week as we open up talking about the simple pleasures in life. Florida Man takes us on a quick trip to Ohio involving an arrest and some drugs. Kevin has his weekly Dad Tip with great advice. Chris has the latest Random Twitter Finds and it gets a little warm with the crew. Jose is live with WWFU but has no financial lessons this week. We wrap up the episode with Movie Time with a bonus of ...
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May 13, 2025 • 62 mins
Rank the most toxic College Football fan bases MLB: -Fantasy Studs & Duds NFL: -Pickens to the Cowboys; -Jags cut Gabe Davis; Is he washed or still have a chance somewhere? (Giants) -Reed worried about where he stands? FSU Update: -Baseball vs Cal -Softball ACC Tournament Follow us at Cuptocupshow ON ALL SOCIAL (no-spaces) The CTC Onlyfans on FB Cuptocuplife.com
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May 8, 2025 • 75 mins
It’s a trio crew this week as we open up talking about our top three actors when we were growing up. Florida Man takes us to Lake Eola Park in Orlando involving swans. Chris has a new Random Twitter Finds that the guys actually seem to enjoy. Kevin has his weekly Dad Tip and Jose has quite the financial wellness class during WWFU. Chris has an I Don’t Get It and Chase wraps it up with Trivia. Special thanks to Blair and Hender...
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May 6, 2025 • 54 mins
Opening Item NFL Fan Base Tier List MLB: -Fantasy Studs & Duds -FSU Update: -Baseball vs Clemson -Jordan Travis -Softball ACC champs NHL: -J is locked in for the Caps -Historically not good for the Avs and Wild Follow us at Cuptocupshow ON ALL SOCIAL (no-spaces) The CTC Onlyfans on FB Visit our site at Cuptocuplife.com (nospaces)
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May 1, 2025 • 102 mins
We open up the episode this week talking about something that we just can’t seem to understand. Florida Man has a chance for the Big Board and it involves some Dragon Ball Z. It’s been a minute but Fill in the Blank is back involving male stereotypes, new hobbies and fast food items. Jose has the next WWFU for the crew and Kevin has a unique Dad Tip this week. Chris wraps up the episode with the latest Am I An Asshole. Special t...
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April 29, 2025 • 72 mins
Its sports... NFL: -Draft Recap - Shadeur prank/fall -Awkward Bill Belicheck interview; MLB: -Fantasy Studs & Duds - how long until Jose stops setting his lineup (1-4 on the year) -Braves finally turning it around? NHL: -NHL Playoffs update FSU Update: -Baseball vs Louisville Cuptocuplife.com
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April 24, 2025 • 125 mins
It’s a full squad this week and it’s a championship episode! We open up talking about something we never thought would happen to us. Florida Man takes us to Brevard County involving a Subway. Chris has the latest Blind Rankings involving movie characters. We have the Chicken Tender Bracket Championship between #1 Publix and #2 Zaxby’s. Chase has the next She’s Always Right and Jose has the latest WWFU. Kevin has his usual Dad Ti...
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