Kadeem Phillip & Jack Simon

Wrestling With Wromance

Sports EN ↓ 68 episodes

Discover the unlikely connection that emerged from a Zoom watch-along of our favorite weekly wrestling show, evolving into a captivating conversation about our greatest passions: life and ‘wrasslin.’ Welcome to ‘Wrestling with Wromance,’ where Wrestling zealot Kadeem and romantic wreck Jack Simon take center stage. Every week, we unite to dissect the latest wrestling news, unravel the possibilities of the wrestling world’s future, and embark on a journey into Jack’s tumultuous dating life. Join us as we share moments of unbridled optimism, plunge into the depths of despair, doom and delve into...

Author

Kadeem Phillip & Jack Simon

Category

Sports

Podcast website

redcircle.com

Latest episode

May 21, 2026

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Episodes

“Caffeinated Chaos (Extra Shots of Wrestling Opinions)” 21.05.2026

On this episode of Graps & a Cup of Coffee , it’s nothing but caffeinated chaos as we dive into everything happening across wrestling right now. We start in AEW with something we’re really enjoying—the Darby Allin title reign. What it is, what it’s building toward, and why it might mean more than it looks on the surface. From there, we break down the Will Ospreay storyline, the road to Double...

Venti Double Shot Express-o 28.04.2026

After a two-week break, Graps & a Cup of Coffee is back on the grind with a Venti Double Shot of conversation. With WrestleMania season in the rearview and AEW continuing to shift and evolve, we’re catching up on everything that’s been happening across the wrestling world. From current title pictures and ongoing storylines in AEW to breaking down the recent WWE releases, there’s a lot to unpac...

Brewing Chaos in the Wrestling Community 11.04.2026

Grab yourself a cup of coffee and tap in—this is another episode of  Graps and a Cup of Coffee . ☕🎙️ This time, we’re diving into the weird and wild dynamics of the internet wrestling community, starting with Ricochet and his… complicated relationship with it. From there, I’m sharing my thoughts on the debut of Blackheart Lio Rush, and what it all means in the bigger picture. We’re also getting i...

Life, Drama, and a Brown Sugar Espresso 18.03.2026

On this episode of Graps and a Cup of Coffee, we’re playing catch-up on everything life pulled me away from—because yeah… life really be life-ing, fam. While sipping on a smooth brown sugar espresso, we get into all the latest, from the Roman/Punk/“dead father” drama to Jade and Rhea making waves. I also talk about the excitement around Oba Femi stepping into the Brock Lesnar lane, plus that stern...

Graps & A cup of coffee Ep1: A new day 28.02.2026

It’s been a long time… so excuse the rust. Welcome to a new era of Graps and a Cup of Coffee. You may have heard the name before — but starting now, it means something different. This isn’t just a quick wrestling talk. This is a reset. A rebrand. A retooling of everything you thought this series was. Hosted by Kadeem “LifeofDeem,” this version of Graps and a Cup of Coffee is where passion meets pe...

“Back Like We Never Left” 20.04.2025

After an unexpected hiatus,  Wrestling with Wromance  is back! Life’s been wild for both of us—new chapters, new chaos—but we’re back in the ring (well, the podcast booth). In this episode, Jack spills the tea on his Russian sugar mama before we dive headfirst into the madness that is  WrestleMania week . From the PR disasters WWE’s been juggling, to our honest takes on the build-up, and the match...

“Room Temperature Takes & Real-Time Risks” 28.03.2025

After a short hiatus, Wrestling with Wromance is back! Jack and Deem return to the mic, catching up on the whirlwind of life that’s been keeping them busy. Jack opens the episode with a story about someone from his past — someone who once ghosted him — and asks Deem for advice on whether he should reach out. What follows? Jack actually tries Deem’s advice live on air, and let’s just say… things ge...

Soul for a Soul & Naive mistakes 04.03.2025

On today’s episode of  Wrestling with Romance , Jack kicks things off with a story about a hilariously naïve mistake he made. From there, we break down the Cody Rhodes vs. The Rock promo segment, specifically when Rock said he  wants  Cody’s soul—what does it mean for WrestleMania? Quick heads-up: This episode was recorded  before  Elimination Chamber, so if some of our predictions sound outdated,...

Love, Lost Opportunities, and WrestleMania Predictions 18.02.2025

On today’s episode, Jack and Kadeem kick things off with a conversation about Valentine’s Day. Jack reveals that he’s never had a relationship last through the holiday, leading to a deeper discussion about his past relationships and how that experience has shaped him. Things take an unexpected turn when Jack opens up about nearly landing a run in Pro Wrestling NOAH, only for WWE to bring him back—...

The Trial of John Cena (Rumble Recap) 11.02.2025

On today’s episode of  Wrestling with Wromance , Kadeem and Jack kick things off with a debate on what truly counts as ghosting. At what point does a conversation—or lack thereof—cross into ghosting territory? This discussion stems from a recent conversation Kadeem had with a friend. From there, the duo dives into the  Royal Rumble , breaking down their thoughts on the show. They share their mixed...

Let’s get ready to Rumble 04.02.2025

On today’s episode of  Wrestling with Wromance , we kick things off with a conversation sparked by an off-air chat Kadeem had with a friend who had never heard the podcast before. As they caught up, the friend had some interesting thoughts about Jack, which led to Kadeem bringing a thought-provoking question to the pod. What followed was a deep, unexpected, and very interesting discussion. From th...

Love is Priceless 25.01.2025

In today’s episode of  Wrestling with Wromance , Kadeem and Jack dive into a thought-provoking conversation that stems from a playful debate with their friends: “Is Jack’s love cheap?” This leads to a heartfelt discussion about Jack’s approach to love and relationships, offering an unexpectedly emotional moment for the duo. From there, they shift gears to recap the past week in wrestling, reflecti...

What a week 14.01.2025

Welcome back, and happy 2025! We’re kicking off the new year with a brand-new episode of Wrestling with Romance ! After an unexpected hiatus (life happens), Kadeem and Jack are back to bring you the wrestling talk you’ve missed. This week, we’re diving into some exciting and unexpected topics: • First, we wrap up the story Kadeem teased in our last episode—a relationship tale that took a surprisin...

“Whole Lotta Wrestling“ 13.12.2024

On today’s Wrestling with Romance, Kadeem and Jack dive into an intriguing mix of personal stories and wrestling takes. First, Jack recounts his latest date—with a sexologist—and shares some eye-opening insights about her and her fascinating job. (Heads up: Viewer discretion is advised, and headphones are recommended if you’re at work!) From there, the duo jumps into a recap of this week’s wrestli...

The Big 30 under 30 13.12.2024

In this episode, Kadeem tackles the topic of getting back out there after a disappointing dating experience. As someone newly single, he’s exploring how to find his footing, and with Jack’s unique, Darby Allin-style approach to dating, Kadim tries to pick his brain. The conversation then shifts to a GCW vs. AEW discussion, and Jack takes a moment to give TNA its long-overdue flowers in light of th...

Thanksgiving Slamboree 30.11.2024

On today’s episode of Wrestling with Wromance , Jack kicks things off with one of his wild and unforgettable life stories, the perfect follow-up to a cozy Thanksgiving break. From there, we dive into the drama surrounding GCW and AEW. We break down Effie’s controversial comments about Tony Khan, the backlash they sparked, and whether GCW truly has a reason to be upset with AEW. Next, we tackle the...

Mega Church, War Games, Death Riders & C2 “50th episode!” 21.11.2024

🎙️  Today on Wrestling with Wromance , we’re bringing you a mix of storytelling, wrestling analysis, and fantasy booking! Jack kicks things off with a palate-cleansing tale about his unexpected experience at a mega church event in the Barclays Center, a surprising connection he made, and how a simple interaction can leave a lasting impression. From there, we dive into the Moxley  Death Rider  stor...

The Sex Fight Club Dungeon 11.11.2024

On this episode of Wrestling with Romance , Jack takes us on a wild ride, sharing his unexpected adventure at a Fight Club-themed party with a twist. He dives into all the unforgettable moments, setting the stage for some deep conversation. From there, we shift to the world of wrestling as we explore the appeal of “glorified jobbers” and the unique roles they play in the industry. Next up, we disc...

Rose-tinted Nostalgia Glasses 30.10.2024

On this episode of Wrestling with Romance , we’re back and excited to reconnect with you! Jack kicks things off with a story fresh from his recent trip to Chile—a tale unfolding in real time that’s sure to surprise. Then, we dive into Jack’s aversion to ’90s wrestling and the fans who seem stuck in nostalgia. We discuss how “rose-tinted glasses” affect perspectives on wrestling’s past and share so...

Graps & A Cup of Coffee 17.10.2024

We’re trying something brand new with today’s episode! Welcome to the pilot of our latest series: Graps and a Cup of Coffee ☕️. When life gets busy, we still want to keep the wrestling talk going, so this is our way to have a quick chat while sipping coffee. Think of it as a casual, catch-up conversation—just 10-30 minutes of pure wrestling fun. No need for the hour-long deep dives, just short an...

This Isn’t Cinema 27.09.2024

On today’s episode of Wrestling with WRomance, Jack and Kadeem dive into the challenges of handling rejection in the dating world. They discuss their strategies for coping, how they push forward, and keep their heads held high. Jack then shifts gears to share what’s been on his mind: wrestling fans using the term ‘cinema’ and why, as a film critic and filmmaker, it bothers him. Kadeem follows up w...

The enemy of my enemy 19.09.2024

On this week’s episode of *Wrestling with Wromance*, Kadeem continues to share the story behind his situationship/relationship with “S” and how it eventually comes to a conclusion. Following that, Jack introduces Kadeem to *Wrestle Society X*, a show he had never heard of before, leaving him completely mind-blown. Kadeem then dives into a conversation about how wrestling fans often exhibit racism...

The Darkest Timeline 13.09.2024

In this week’s episode of Wrestling with Wromance, Jack kicks things off by asking Kadeem about his worst date experience, which leads to a hilarious and unforgettable story about a date with an ex. From there, the duo dives into a review of AEW All Out, sharing their favorite matches and standout moments from the show. To wrap it up, they discuss the biggest missed opportunities in wrestling due...

Going All Out 04.09.2024

In this week's episode of *Wrestling with Wromance*, Jack kicks things off by discussing potential relationship deal breakers. The conversation then shifts to the surprising news of Odyssey Jones' possible release. Kadeem touches on this during a segment about recent developments involving Triple H and some allegations made by MVP, emphasizing that this was recorded before the domestic abu...

Hell Of A Show 30.08.2024

In this episode of Wrestling with Romance, Jack kicks things off with an incredible story about introducing his friends to the world of wrestling by showing them the chaotic match between Necrobutcher and Samoa Joe—a choice that leaves Kadeem questioning his sanity. From there, we dive into a full review of AEW’s All In, sharing our thoughts on how the show delivered, highlighting our favorite mom...

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