Josh and Craig are joined by Dave Hemmingson to revisit “Third Wheel,” the Season 3 fan-favorite where newly single Ted unexpectedly finds himself navigating the possibility of a threesome with returning guest stars Busy Philipps and Danica McKellar. Dave talks about joining the writers’ room during a pivotal moment for the series, helping launch the “free-range Ted” era after the Robin breakup, and crafting the episode’s frantic, almost real-time energy inspired by farce and physical comedy. The group digs into Barney’s surprising vulnerability, Marshall and Lily’s enthusiastic “mission control” support of Ted’s big night, the origins of the tramp stamp storyline, and whether Ted actually “won the belt.” Along the way, they reflect on why the episode still works: balancing absurd comedy, emotional honesty, and one of the weirdly sweetest stories HIMYM ever told.

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Josh and Craig talk about “We’re Not From Here,” the second half of the Gael mini-arc, and how the episode feels a little more like a classic sitcom with three separate storylines: Robin trying to make a vacation romance work in real life, Ted and Barney pretending to be tourists to pick up women, and Marshall freaking out over Lily’s “death letter.” They laugh a lot about Jason Segel’s completely committed insanity, Robin almost pulling a gun on people, Ted passionately defending New York over New Jersey, and how absurdly old they made Marshall and Lily look in the 2029 flash-forward. They also talk about Chris Harris’ writing style, Enrique Iglesias’ guest spot, and how Ted in early Season 3 is trying really hard to become less “romantic Ted” after the breakup. The episode ends with a really sweet surprise letter from producer Emily Blumberg about growing up loving HIMYM and eventually winding up working on the podcast.

CONNECT WITH THE SHOW:

Official Website (Send us your audio and written messages)

Instagram

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READ JOSH’S MUSELETTERS ON SUBSTACK:

Subscribe HERE

CRAIG’S BOOK IS AVAILABLE!

Head over to CRAIG’S WEBSITE to order your copy of THAT’S NOT HOW IT HAPPENED.

SUPPORT PEDIATRIC CONGENITAL HEART DISEASE RESEARCH:

Click HERE to learn more and donate today.

FOLLOW THE OFFICE LADIES:

Check out "Office Ladies" at https://officeladies.com/ or wherever you get your podcasts!

Follow on Instagram: OfficeLadiesPod

Follow on TikTok

AND MORE:

Josh’s Official Website

Josh on Spotify

Craig’s Official Website (with links to his published writing)

Alek’s “Dead Fathers Society” on Substack

On another very special Bonus Episode of HWMYM, we’re bringing you a table read of Gimme Five, a second pilot that Craig and Carter (wrote not long after HIMYM ended). And once again, this pilot never got made (until now!). They co-wrote this pilot with legendary writer Peter Tolan, whose credits include The Larry Sanders Show, Rescue Me, Analyze This, Analyze That, and many more.

Here's the log line: It's 1985, and Gimme Five is the number two family sitcom in America. But behind the scenes of this feel-good show is a dysfunctional workplace family on the verge of self-destruction. Showrunner Cliff McConnell must somehow keep it together and keep being funny in the midst of his newborn son's health crisis.

Sharp, outrageous, and wildly funny, Gimme Five gives a behind-the-scenes look at comedy writing that feels both absurd and strangely authentic. It may also be one of the funniest pilots ever featured on Dead Pilots Society.

Major Content Warning *salute* — Definitely think twice about listening to this one with small children in the room. You may hear something that offends you early on in this pilot, but please stick with it.

Our cast for the show includes Taran Killam (SNL, High Potential, Stumble), Chris Diamantopoulos (Beavis and Butthead, Silicon Valley), Scott Foley (Scandal, Scream 7), Dallas Goldtooth (Reservation Dogs), Tami Sagher (Inside Amy Schumer), Chris DiStefano (stand up), James Urbaniak (Venture Brothers), Isabella Gomez (One Day at a Time, Shrinking), Cyrina Fiallo (High Potential, 911 Lonestar), Alyssa Limperis (What We Do In the Shadows), Burl Moseley (Crazy Ex-Girlfriend).

Follow Dead Pilots Society on ⁠Apple Podcasts⁠, or wherever you get your podcasts.

CONNECT WITH THE SHOW:

⁠Official Website⁠ (Send us your audio and written messages)

⁠Instagram⁠

READ JOSH’S MUSELETTERS ON SUBSTACK:

Subscribe ⁠HERE⁠

CRAIG’S BOOK IS AVAILABLE!

Head over to ⁠CRAIG’S WEBSITE⁠ to order your copy of THAT’S NOT HOW IT HAPPENED.

SUPPORT PEDIATRIC CONGENITAL HEART DISEASE RESEARCH:

Click ⁠HERE⁠ to learn more and donate today.

FOLLOW THE OFFICE LADIES:

Check out "Office Ladies" at ⁠https://officeladies.com/ ⁠or wherever you get your podcasts!

Follow on Instagram: ⁠OfficeLadiesPod⁠

Follow on ⁠TikTok⁠

AND MORE:

⁠Josh’s Official Website⁠

⁠Josh on Spotify⁠

⁠Craig’s Official Website⁠ (with links to his published writing)

⁠Alek’s “Dead Fathers Society” on Substack⁠