We Should Date

Episode

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  Deb Chubb 20.09.2026 1j

  Deb goes from The Challenge to another challenge trying to avoid Michael’s tactics. They also dive into relationship dealbreakers, why you should never leave a hamster near a staircase, and debate whether owning a boat makes someone a catch. This episode is a constant battle of wits. Will this date end with a real connection, or are they destined to just be friends after evaluating each other’s dating red flags? Watch the full episode to find out!
• 
  Andrea Jin 13.09.2026 54mnt

  Things get incredibly interesting on the podcast today as we put our chemistry right on the table. We get into the brutal honesty of first impressions, the realities of modern dating, and a highly educational (and horrifying) deep dive into internet fetishes.
• 
  Kayden Kross 06.09.2026 50mnt

  Adult film star, director, and author Kayden Kross joins the show for a conversation that gets surprisingly real, surprisingly fast. We dig into modern dating, relationship dynamics, and what actually makes two people click. Against all odds, the chemistry takes over. Stick around until the end to see the exact moment the bit turned real and I got her number live on the mic.
• 
  Mac Lawson 30.08.2026 37mnt

  In this episode, we’re live on location in South Beach at Lobster Shack! Huge thanks to Lobster Shack for sponsoring the show. If you're in Miami, grab their signature lobster roll and seafood platters. This week, Michael sits down with comedian Mac Lawson. Fun fact: they actually matched on Bumble years ago, made zero progress as a couple, but somehow turned it into a hilarious friendship. They dive deep into modern dating app disasters, what it’s like matching with fellow comics, and why South Beach brings out the wild side in everyone.
• 
  Katherine Blanford 23.08.2026 56mnt

  The hilarious Katherine Blanford stopped by the studio, and things got wonderfully silly, real fast. From trading ridiculous stories to figuring each other out in real-time, this episode is full of unexpected laughs and maybe... just maybe... a little bit of chemistry?
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  Taquita Love 16.08.2026 57mnt

  Taquita Love brings her soft nurturing energy to the show. Michael and Taquita know each other from the comedy scene and their familiar banter is something to be seen.
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  Rachel Steinberg 2.0 09.08.2026 54mnt

  Rachel reminds Michael he's in the friend zone and will never have a chance to leave it.
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  Zainab Johnson 2.0 02.08.2026 1j 6mnt

  Zainab returns to the podcast only to remind Michael he's bad at flirting and not even her advice can help him.
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  Julia Theis 27.07.2026 1j

  Julie joins Michael to recap their crazy night in Nashville last year. Did that first impression ruin any chances of a romantic relationship?
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  Natalie Cuomo 19.07.2026 59mnt

  Natalie meets Michael for the first time on the podcast. Natalie is very aware of Michael's tactics but he insist what they have is special and real. Will she fall for his charm?
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  Joey Camasta 12.07.2026 50mnt

  Joey Camasta fantasies what it would be like to date Michael. Michael learns what he drastically needs to change about his appearance to become worthy of Joeys love.
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  Kelsey Jensen 05.07.2026 58mnt

  Michael introduces Kelsey with his very first preliminary interview. Will Kelsey & Michael find chemistry? Kelsey is one of the very few dates Michael found from sliding in her DMs.
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  Gabby Bryan 28.06.2026 1j 5mnt

  Gabby Bryan meets Michael for the first time on the podcast. Sparks fly from the start, could this be a new favorite guest? Find out if this New Jersey sweetheart steals Michaels heart.
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  Dana Moon 4.0 21.06.2026 1j

  Dana Moon returns to the podcast, she's grown emotionally and Michael no longer has control of her heart. What does her family think about him though?
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  Madison Lazo & Callista Somers (3some) 14.06.2026 49mnt

  Madison Lazo & Callista Somers flirt with each other while Michael tries to convince a Lesbian to date him.
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  Jiaoying Summers 07.06.2026 54mnt

  Jiaoying Summers is 9 months pregnant but still allowed to flirt with Michael. Just when you thought it couldn't get any weirder, an unexpected guest that interrupts the podcast.
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  Jamie Lee 31.05.2026 1j 11mnt

  Jamie and Michael are on completely different ends of the spectrum when it comes to dating and sexuality.
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  Monarey Martinez 24.05.2026 57mnt

  Monarey and Michael met over 10 years ago in Los Angeles when Monarey first started stand up. They revisit something from their past, was it something or just a friendship?
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  Rayna Greenberg 17.05.2026 1j 10mnt

  Rayna Greenberg & Michael try to keep there hands off each other, the sexual tension is beaming on this episode.
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  Galina Rivina 10.05.2026 57mnt

  Michael makes Galina open up more than she wants, are they compatible?