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

THE BRACKET THAT BROKE US 07/31/2025

THE BRACKET THAT BROKE US Episode 307 is stacked with chaos. We welcome in new guest host Andy and immediately derail with Florida Man impersonations, emotional dad tips, wild 20s advice, and VHS home video nostalgia (complete with broom choreography). Then comes the bracket — action movie heroes go head-to-head and the debate nearly ends the show. Spoiler: Jason loses his mind over T2. Also inside: ⚡️$375 rent war stories ⚡️Why documenting grandma is crucial ⚡️Hookah flashbacks ⚡️Kevin’s actually good life advice (?!) Florida Man, fake prosecutors, and a lot of yelling. Let’s ride. /episode/index/show/cuptocup/id/37617765

7MIH - Whats a Canadian Football 07/29/2025

7MIH - Whats a Canadian Football WTF is the Canadian Football League doing? MLB: -Fantasy Studs & Duds NFL: -Preseason Starts Thursday -Jefferson already injured -Rough start for some QBs -ESPN might be acquiring NFL Network & Redzone? FSU: -FSU Hoops Non-Conference -Buying into Norvell/TC passion from ACC Kickoff? Follow us at Cuptocupshow ON ALL SOCIAL (no-spaces) The CTC Onlyfans on FB /episode/index/show/cuptocup/id/37593665

He Wore Lawn Shoes to the Aquarium 07/24/2025

He Wore Lawn Shoes to the Aquarium This week, the boys are back from vacation and full of hot takes, deep regrets, and even deeper shoe shame. Kevin opens up about the $200 aquarium mistake (and we mean mistake), Jose coughs his way into a 5-minute timeout, and Chase gets roasted from head to toe — mostly because both are covered in gear from 2005. We also dive into: Vacation beard compliments gone too far The Florida Man who stuffed what down his pants?! Our all-time favorite shows (drama, comedy, and sci-fi) Why “The Bear” might just be therapy for men with baggage And what happens when your wife doesn’t trust you behind the wheel Oh — and there's a “Would You Rather” that spirals into space (literally). If you’ve ever overpaid for a family outing, worn your mowing shoes to a public place, or just needed to hear your friends call you out — this episode’s for you. 26:03-27:07 Kevin’s Other Crew 39:11-39:41 Condoms Expensive 48:10-49:03 Old Man Chase 51:20-52:34 Let it Go Chase 52:50-53:48 Lawn Mowing Shoes CuptoCupLife.com /episode/index/show/cuptocup/id/37529400

7MIH - World Champions 07/22/2025

7MIH - World Champions -Would you rather be a fan of a team that nobody talks about or a team that everyone hates? NFL: -ChatGPT predicted the 2025 NFL Playoffs -Which NFL team is currently America’s team? - Where do you have the Steelers now? Additions of Ramsey and Jonu Smith (with Rodgers and DK Metcalf) MLB: -Fantasy Studs & Duds -Make one bold prediction about your team for the rest of the season -Acuna’s Amazing Throw FSU: -Recruiting Class improving 2026 class #11 on 247sports, #12 on On3 or Rivals, #12 ESPN - Odell Haggins new role after 31 years coaching…35 total -No shot FSU is a third tier coaching job? Follow us at Cuptocupshow ON ALL SOCIAL (no-spaces) The CTC Onlyfans on FB Visit our site at Cuptocuplife.com (nospaces) /episode/index/show/cuptocup/id/37503425

FILLED UP BY JOSH! 07/10/2025

FILLED UP BY JOSH! 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 also planning drama, New Year’s chaos, Jose maybe moving, and Kevin catching stray bullets for his hatred of fun. We wrap it up with DAD TIP and some hands-on history, VR war trauma, and a sobering realization that Snoop Dogg still hasn’t replied. Also—major shoutout to our first-time listener Brian… buddy, we’re sorry. /episode/index/show/cuptocup/id/37357165

The Kevin Chronicles: Beards, Beers & Bad Rankings 07/03/2025

The Kevin Chronicles: Beards, Beers & Bad Rankings 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 someone tries to be deep—and gets immediately mocked for it. Also: tailgating stories, podcast shoutouts, and the weekly tradition of saying “Yeah” 93 times. Highlights include: • 🍻 Beers and loneliness: a love story • 🧔 Beards, shirts, and possibly gender identity confusion • 🎮 Twitch follow rage • 🏳️‍🌈 Pride Month... and why it somehow made things worse • 🎤 Kevin getting absolutely torched • 🔥 The worst ranking take of all time (again) It’s all here, wrapped in sarcasm, swear words, and enough inside jokes to alienate new listeners. Classic. Chris's Moments 7:30-8:14 Thanks Dad 29:05-29:43 Florida Man Debates 39:00-39:35 Jose’s Hibernation 1:08:25-1:09:13 Disappointed Dad 1:17:50-1:18:43 Those Types of Books 1:25:15-1:25:53 America’s Favorite State CuptoCupLife.com /episode/index/show/cuptocup/id/37268055

7MIH - Best Sports Logo 07/01/2025

7MIH - Best Sports Logo 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 Steelers – Wild Card (10‑7) Denver Broncos – Wild Card (10‑7) 🌟 National Football Conference (NFC) Detroit Lions – NFC North Champions (15‑2) Philadelphia Eagles – NFC East Champions (14‑3) Tampa Bay Buccaneers – NFC South Champions (10‑7) Los Angeles Rams – NFC West Champions (10‑7) Minnesota Vikings – Wild Card (14‑3) Washington Commanders – Wild Card (12‑5) Green Bay Packers – Wild Card (11‑6) -Jalen Ramsey to the Steelers for minkah Fitzpatrick and a 5th -Is Mahomes a douche for refusing an autograph? Play video FSU: -TC’s comments about Alabama….cocky or confident? FSU QB Thomas Castellanos calls out Bama: "They don't have Nick Saban to save them. I just don't see them stopping me." -Jamir Watkins drafted Follow us at Cuptocupshow ON ALL SOCIAL (no-spaces) The CTC Onlyfans on FB Visit our site at Cuptocuplife.com (nospaces) /episode/index/show/cuptocup/id/37232690

All Those Addictions 06/26/2025

All Those Addictions 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. Special thanks to Antonio and Henderbeard for the voice nuggets. Grab a Twisted Tea or Brisk and enjoy! 13:15-3:38 North Face Jason 25:30-26:45 We Measure Up 27:33-28:20 Who is Taller? 32:20-33:23 More 5’9 Debating 47:30-48:35 Sandwich Debates 57:20-58:05 I Just Wanna…. CuptoCuplife.com /episode/index/show/cuptocup/id/37157275

A PIERCED SAUSAGE 06/19/2025

A PIERCED SAUSAGE 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 Fake for a spot on the Big Board. Grab your favorite drink (maybe a whiskey drink like Kevin) and enjoy. Cheers! /episode/index/show/cuptocup/id/37066605

SAVANNAH BANANAS SUCK? 06/18/2025

SAVANNAH BANANAS SUCK? 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? /episode/index/show/cuptocup/id/37050420

TOP HEAVY, WE READY! 06/12/2025

TOP HEAVY, WE READY! 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 Big 300. We wrap it up with Correct Me If I’m Wrong. Special thanks to Henderbeard and Blair for the voice nuggets. Cheers! /episode/index/show/cuptocup/id/36966475

7MIH - NOLES ARE DEAD AND SO ARE WE!! 06/10/2025

7MIH - NOLES ARE DEAD AND SO ARE WE!! ITS SPORTS....WE DONT REALLY WANNA TALK ABOUT IT THIS WEEK BUT WE DID. FSU, BRAVES, RODGERS, JAIRE ALEXANDER....EVERYTHING SUCKS!!! /episode/index/show/cuptocup/id/36933685

The Big 300! 06/05/2025

The Big 300! 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 us where we messed up and more chances at the Big Board with Name That Show and Name That Sound. Kevin wraps it up with the wildly popular Rapid Fire. Special thanks to Naomi for the voice nugget. Grab some shots or an entire bottle of liquor and enjoy your favorite chaos. Cheers! Chris's Top Moments 5:17-6:07 Not Quite Pride Month 31:25-32:05 Special Date Night 33:00-34:03 Blading Thursday 37:10-38:08 Bears are Cuddly 52:40-53:40 Kev Doesn’t Get the Segment 58:08-58:55 J so Aggressive 1:20:10-1:21:00 Thongs Only Cuptocuplife.com /episode/index/show/cuptocup/id/36838700

Broccoli Salad Sucks 05/29/2025

Broccoli Salad Sucks 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 another edition of Movie Time. Special thanks to Henderbeard for the voice nugget. Grab a drink or a shot and enjoy. Cheers! 8:40-9:55 Kev Still Hates Drinking Games 11:15-12:21 Chase is so Awkward 16:05-16:45 Chris Goes to Timeout 29:50-30:45 Shout Out Sheila 31:05-31:51 Broccoli Salad Sucks 32:00-32:47 Jason’s Broccoli Salad Rant 1:04:47-1:05:25 You Like Books 1:12:20-1:13:10 Don’t Skip Seasons CuptoCupLife.com /episode/index/show/cuptocup/id/36764070

7MIH - Best NLF Records in 2025 05/27/2025

7MIH - Best NLF Records in 2025 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) /episode/index/show/cuptocup/id/36727475

Rage in the Apples 05/22/2025

Rage in the Apples 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 Mike and Henderbeard for the voice nuggets. Grab your favorite drink and enjoy! Cheers! Chris's Top Moments 5:10-5:43 Cringe Top Gun 9:05-9:43 Rage in the Apples 17:30-18:25 Kevin’s Hearing Problem 31:40-32:40 Taco Bell Nuggets 41:30-42:05 Flubber 2 53:50-54:16 Amazing Moment of Cringe 1:00:23-1:00:52 Kevin’s Reactions Cuptocuplife.com /episode/index/show/cuptocup/id/36663990

7MIH - Guess the Year 05/20/2025

7MIH - Guess the Year 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) /episode/index/show/cuptocup/id/36635855

It’s Small But It Works 05/15/2025

It’s Small But It Works 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 TV shows. Special thanks to Blair and Henderbeard for the voice nuggets. Get ready for all the breaking news on the episode. Cheers! Chris's Top Moments 6:04-6:30 Small But Works 9:30-10:31 Kevin Hates the Beach 31:05-31:35 Them Biceps 48:54-49:24 The Safe Word 50:55-51:30 Dirty Talk 54:10-55:00 We Suck at Dirty Talk 57:30-57:55 Where is She? 58:40-59:20 Don’t Tell Me What To Do Cuptocuplife.com /episode/index/show/cuptocup/id/36573255

7MIH - The Most Toxic College Football Fan Bases 05/13/2025

7MIH - The Most Toxic College Football Fan Bases 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 /episode/index/show/cuptocup/id/36547005

Leave the Swans Alone 05/08/2025

Leave the Swans Alone 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 Henderbeard for the voice nuggets. Grab a loaded Corona and enjoy. Cheers! 9:15-10:13 Worst Movies Ever? 12:50-13:48 Friday Night Movies 21:06-21:46 Chase Feeling Frisky 27:15-27:58 No Itching 35:15-36:10 Middle School Chris 44:58-45:31 Only at Spencer’s 53:40-54:25 Not Having the Talk CuptoCuplife.com /episode/index/show/cuptocup/id/36480055

7MIH - Top 5 Nole QBs 05/07/2025

7MIH - Top 5 Nole QBs 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) /episode/index/show/cuptocup/id/36462915

Being Pickled 05/01/2025

Being Pickled 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 thanks to Naomi and Henderbeard for the voice nuggets. Grab a seltzer and make sure to charge your computer. Cheers! Chris's Top Moments 4:00-5:05 Good For You Chase 22:00-22:26 Awkward Segment Opening 36:00-36:38 Ham is Bold? 39:45-40:13 Join the CDC 54:25-54:50 Kev Loves Pork Chops 1:10:25-1:10:57 Do You Check? 1:11:15-1:12:00 Basic Burger Kevin Cuptocuplife.com /episode/index/show/cuptocup/id/36381520

7MIH - The Winningest Pro Teams 04/29/2025

7MIH - The Winningest Pro Teams 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 /episode/index/show/cuptocup/id/36354560

The Safety Is On 04/24/2025

The Safety Is On 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 Tip and Chris wraps up the episode with Movie Talk. Special thanks to Henderbeard and Blair for the voice nuggets. Grab a chicken tender and enjoy. Cheers! Chris's Top Moments 8:00-8:35 Swing And a Miss 29:30-30:13 The Bus Driver 35:10-36:20 “It’s Not a Gun” 52:00-52:45 Jason is so Happy 56:30-57:30 Kevin Big Mad 1:31:00-1:31:35 Every Single Week 1:51:45-1:52:44 No Maids at Kevin’s Cuptocuplife.com /episode/index/show/cuptocup/id/36292645

7MIH - Live Sporting Events 04/22/2025

7MIH - Live Sporting Events Its sports... Opening: How many sporting events have you been to in the last year? MLB: Fantasy Studs & Duds NFL: **PLAY DRAFT SOUND AT THE BOTTOM** The Draft is this week. Hopes for your team? Jalen Ramsey leaving the Dolphins? NHL Playoffs! FSU Update: FSU United Should the MC be at more baseball games? Charlie Ward to FAMU CFB Notes: Corso retiring; Colorado jersey retirements are stupid Follow us at Cuptocupshow ON ALL SOCIAL (no-spaces) The CTC Onlyfans on FB Visit our site at Cuptocuplife.com (nospaces) /episode/index/show/cuptocup/id/36261390

Soggy Salads 04/17/2025

Soggy Salads It’s a full squad and Jason is keeping us on a tight schedule. We open up talking about food we dislike now but loved as kids. Florida Man visits North Carolina and invokes a machete. Jose has a special I Don’t Get It and we have our second Final Four matchup of the Chicken Tender Bracket featuring #2 Zaxby’s vs. #3 Chick-fil-A. Jose has a longer edition of WWFU and also surprises us with his own Dad Tip. Special thanks to Blair and Henderbeard for the voice nuggets. Grab your favorite soggy salad and enjoy your favorite podcast. Cheers! Chris's Top 5 6:25-6:52 Little Kid Chris 13:50-14:33 Geography Lesson 25:50-26:42 Don’t Call Jose 40:10-40:56 Kevin’s Bracket Vote 41:40-42:50 No Tenders for Kevin TWITCH!!!!!! VIDEO ON SPOTIFY (FOLLOW AND COMMENT) Follow us at Cuptocupshow ON ALL SOCIAL (no-spaces) The CTC Onlyfans on FB Visit our site at Cuptocuplife.com (nospaces) Check out our merch store /episode/index/show/cuptocup/id/36204500

7MIH - NFL Superlatives 04/15/2025

7MIH - NFL Superlatives MASTERS—BOOM MLB: -Fantasy Studs & Duds -Biggest shock of the season so far NFL: -NFL Superlatives FSU Update: -Baseball vs VT -Football Savior QB is out -Shout out J Follow us at Cuptocupshow ON ALL SOCIAL (no-spaces) The CTC Onlyfans on FB Visit our site at Cuptocuplife.com (nospaces) /episode/index/show/cuptocup/id/36151730

Which is the Pre-C*m Baby? 04/10/2025

Which is the Pre-C*m Baby? It’s the full squad this week with all the chaos. We open up talking about useless things that we remember. Florida Man involves yet another arrest involving drugs and a firearm. It’s time Final Four of our Chicken Tender Bracket between #1 Publix and #5 Guthrie’s. Chase has a What’s That Sound for the Big Board and Kevin has his weekly Dad Tip. Jose has the latest WWFU and Kevin has a Picture Time that he had planned for weeks. Special thanks to Henderbeard, Naomi and Blair for the voice nuggets. Grab your favorite drink and enjoy the arguments. Cheers! Chris's Top 5 6:05-7:00 They Do Exist 14:30-14:58 Candace Cameron Letter 30:00-30:35 Which One Was It? 44:00-45:17 Publix Worth The Wait? 56:00-57:01 More Tenders Debate CuptoCupLife.com /episode/index/show/cuptocup/id/36081875

7MIH - Most Frustrating Things about Sports 04/08/2025

7MIH - Most Frustrating Things about Sports Its sports... Most frustrating things in sports? NFL…Tyreek gettin traded? PLAY VIDEO -March Madness update -Duke have one of the biggest MM chokes ever? https://www.facebook.com/share/v/1AGLR6fLSW/?mibextid=wwXIfr -FSU Update: -Baseball v Jacksonville/WF -Terance Mann Hoops Assistant GM -MLB: -Fantasy Studs & Duds -Ovechkin sets record Blind Rankings Cuptocuplife.com /episode/index/show/cuptocup/id/36051350

Go To Better States 04/03/2025

Go To Better States It’s a full squad for the first time this month! We open up talking about childhood snacks that have disappeared. Florida Man takes us to Martin County and involves an arrest. We continue the Chicken Tender Bracket with the final Elite Eight matchup between #10 KFC and #3 Chick-fil-A. Chase has his latest Name That Movie/Show and Kevin has his weekly Dad Tip. Jose has some content for WWFU this week and Chris wraps it up with a Random Twitter Finds that seems awfully familiar. Grab your favorite drink and enjoy the chaos. Cheers! 4:20-5:05 Face Your Fears 5:45-6:43 Tornado Alley 10:58-11:35 Who Likes Butterfingers? 11:45-12:37 Kevin’s ADD 16:35-17:38 We know RICE 37:59-38:50 Guthrie’s Coast to Coast 55:00-55:34 Sober Chase v Drunk Kev 57:19-57:57 The Man Ring CuptoCupLife.com /episode/index/show/cuptocup/id/35984030

Cup to Cup | The Comedy Podcast

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