In this episode of How We Made Your Mother, Josh and Craig revisit “Best Prom Ever,” which features Alek’s memorable (well, to him) cameo as Todd. They reflect on the episode’s big themes—Lily’s growing doubts, the anxiety of adult commitment, and the bittersweet grief that comes with making life choices. The conversation also includes a heartfelt listener message from Jesse, a longtime trans fan of the show, which prompts a thoughtful, honest discussion about how comedy evolves, the importance of inclusive language, and owning past mistakes. The team also unpacks behind-the-scenes stories from filming the prom sequence, shares how Scooter (David Burtka) was introduced, and celebrates the first appearance of the show’s unofficial house band, The 88.

Read Craig’s piece “Hollywood and the R-Word” here in the Boston Globe.

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CONNECT WITH THE SHOW:

Official Website (Send us your audio and written messages)

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HOW YOU MAKE A DIFFERENCE

Donate to our ongoing campaign to support congenital heart disease research

AND MORE:

Josh’s “Museletters” on Substack

Josh’s Official Website

Josh on Spotify

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

Alek’s “Dead Fathers Society” on Substack

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In this General Questions episode following Mary the Paralegal, Josh, Craig, and Alek explore fan-submitted questions ranging from the origins of catchphrases like “Lawyered” and the logic behind character names, to deeper themes like miscommunication and the emotional cost of avoiding vulnerability. They reflect on moments from the show that became iconic (telepathic conversations, Barney’s antics, mustache-on-TV gags), and share behind-the-scenes details like how Buzz Aldrin inspired Lily’s last name. They also dive into how assumptions, pretending, and silence shaped the story of Mary the Paralegal, and how telepathy became a comedic counterpoint to all the unspoken truths.

Questions Alek asks in this episode:

Who came up with “Lawyered”?

Was Marshall based on your friend Noah?

How did you decide on the characters’ last names?

What was the original idea behind “Aldrin”?

What was the inspiration for the “telepathic conversation” bit?

Was the “MadTV” VHS tape on purpose?

How much damage do we do when we make assumptions instead of asking the hard questions?

And why is pretending always easier than being vulnerable?

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CRAIG’S BOOK IS AVAILABLE FOR PRE-ORDER!

Head over to CRAIG’S WEBSITE to pre-order your copy of That’s Not How It Happened today.

And if you’re a business with big orders to fulfill, Amplifier is there to help growing consumer brands and influencers create a unique experience for their customers during the fulfillment process. Visit AMPLIFIER to learn more, and name-drop How We Made Your Mother for special pricing for your emerging brand's program.

CONNECT WITH THE SHOW:

Official Website (Send us your audio and written messages)

Substack (Join the mailing list, get announcements, and read more from Josh and Craig)

Instagram

HOW YOU MAKE A DIFFERENCE

Donate to our ongoing campaign to support congenital heart disease research

AND MORE:

Josh’s “Museletters” on Substack

Josh’s Official Website

Josh on Spotify

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

Alek’s “Dead Fathers Society” on Substack

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This episode features the long-awaited guest appearance of director Pam Fryman, who helmed nearly every episode of How I Met Your Mother. Josh and Craig share stories of how Pam shaped the show’s tone, protected its emotional core, and created a supportive, joyful set culture that lasted nine seasons. They also look back at the episode “Mary the Paralegal,” reliving Sandy Rivers’ debut, Ted’s misguided date, and the first-ever “lawyered” and telepathy jokes. The group reflects on the challenges of shooting without a live audience, the benefits of breaking sitcom norms, and one outdated line they wouldn’t include today. The show opens and closes with moving fan letters that highlight just how deeply HIMYM continues to connect.

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CRAIG’S BOOK IS AVAILABLE FOR PRE-ORDER!

Head over to CRAIG’S WEBSITE to pre-order your copy of That’s Not How It Happened today.

And if you’re a business with big orders to fulfill, Amplifier is there to help growing consumer brands and influencers create a unique experience for their customers during the fulfillment process. Visit AMPLIFIER to learn more, and name-drop How We Made Your Mother for special pricing for your emerging brand's program.

CONNECT WITH THE SHOW:

Official Website (Send us your audio and written messages)

Substack (Join the mailing list, get announcements, and read more from Josh and Craig)

Instagram

HOW YOU MAKE A DIFFERENCE

Donate to our ongoing campaign to support congenital heart disease research

AND MORE:

Josh’s “Museletters” on Substack

Josh’s Official Website

Josh on Spotify

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

Alek’s “Dead Fathers Society” on Substack

THANK YOU TO OUR SPONSORS:

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In this General Questions episode following Nothing Good Happens After 2 A.M., the hosts dive into the fan reactions and deeper themes behind Ted and Robin’s decisions, exploring moral ambiguity, emotional neediness, and the push-pull dynamics of late-night choices. They reflect on the enduring relevance of these situations—romantic longing, blurred boundaries, and personal regrets—and how the show’s framing device allows for layered interpretation of behavior that’s questionable but deeply human. Production details come up too, including why they didn’t shoot a costly Ashley Williams cutaway and what wedding episodes really cost. They also reflect on the end of season one, revealing how uncertain and scrappy things still felt, even after renewal.

Fan Questions We Attempt to Come Close to Answering:

How were the questions this week for “Nothing Good Happens After 2 A.M.”?

Is Robin to blame, and was it written that way or left open to interpretation?

Was there pushback about showing Ted in such a morally gray light?

Do you feel the show’s narrator softens the blow of Ted’s behavior?

What was the inspiration behind Victoria?

How much did that wedding episode really cost?

Were you excited or nervous approaching the end of season one?

Is Buttercup a real bakery in New York?

GET YOUR MERCH!

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CRAIG’S BOOK IS AVAILABLE FOR PRE-ORDER!

Head over to CRAIG’S WEBSITE to pre-order your copy of That’s Not How It Happened today.

And if you’re a business with big orders to fulfill, Amplifier is there to help growing consumer brands and influencers create a unique experience for their customers during the fulfillment process. Visit AMPLIFIER to learn more, and name-drop How We Made Your Mother for special pricing for your emerging brand's program.

CONNECT WITH THE SHOW:

Official Website (Send us your audio and written messages)

Substack (Join the mailing list, get announcements, and read more from Josh and Craig)

Instagram

HOW YOU MAKE A DIFFERENCE

Donate to our ongoing campaign to support congenital heart disease research

AND MORE:

Josh’s “Museletters” on Substack

Josh’s Official Website

Josh on Spotify

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

Alek’s “Dead Fathers Society” on Substack

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Josh and Craig dive into the season one favorite “Nothing Good Happens After 2 A.M.” and talk about ghost stories, juice excuses, and bad decisions made in the middle of the night. They break down why this episode feels more like a play than a sitcom, how Ted gets pulled in every direction (and lies to everyone), and why the moral center of the show still holds up. They celebrate Alexis Denisof’s perfect intro as Sandy Rivers, shout out the music choices, and read two moving fan letters about how the show helped people through hard times.

GET YOUR MERCH!

We’ve got HWMYM merch, which is now just a FEW CLICKS AWAY.

CRAIG’S BOOK IS AVAILABLE FOR PRE-ORDER!

Head over to CRAIG’S WEBSITE to pre-order your copy of That’s Not How It Happened today.

And if you’re a business with big orders to fulfill, Amplifier is there to help growing consumer brands and influencers create a unique experience for their customers during the fulfillment process. Visit AMPLIFIER to learn more, and name-drop How We Made Your Mother for special pricing for your emerging brand's program.

CONNECT WITH THE SHOW:

Official Website (Send us your audio and written messages)

Substack (Join the mailing list, get announcements, and read more from Josh and Craig)

Instagram

HOW YOU MAKE A DIFFERENCE

Donate to our ongoing campaign to support congenital heart disease research

AND MORE:

Josh’s “Museletters” on Substack

Josh’s Official Website

Josh on Spotify

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

Alek’s “Dead Fathers Society” on Substack

THANK YOU TO OUR SPONSORS:

PrettyLitter: Save 20% on your first order and get a free cat toy at prettylitter.com/HWMYM

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Josh and Craig dive into Season 1, Episode 17, “Life Among the Gorillas,” where Marshall starts to lose himself in a toxic corporate job, raising big questions about identity, money, and what it means to be a man. They talk about peer pressure in your 20s, the real cost of selling out, and how the show handled financial stress in a way most sitcoms didn’t. They also touch on the long-distance struggles of Ted and Victoria, the genius of the episode’s cliffhanger, and share stories about early mentors who helped them believe in their creative paths. Plus, a surprise and sweet letter from production designer Steve Olson.

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We’ve got HWMYM merch, which is now just a FEW CLICKS AWAY.

CRAIG’S BOOK IS AVAILABLE FOR PRE-ORDER!

Head over to CRAIG’S WEBSITE to pre-order your copy of That’s Not How It Happened today.

And if you’re a business with big orders to fulfill, Amplifier is there to help growing consumer brands and influencers create a unique experience for their customers during the fulfillment process. Visit AMPLIFIER to learn more, and name-drop How We Made Your Mother for special pricing for your emerging brand's program.

CONNECT WITH THE SHOW:

Official Website (Send us your audio and written messages)

Substack (Join the mailing list, get announcements, and read more from Josh and Craig)

Instagram

HOW YOU MAKE A DIFFERENCE

Donate to our ongoing campaign to support congenital heart disease research

AND MORE:

Josh’s “Museletters” on Substack

Josh’s Official Website

Josh on Spotify

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

Alek’s “Dead Fathers Society” on Substack

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Was Victoria going to be the mother if the show was canceled early? Find out!

In this General Questions episode of How We Made Your Mother, Josh, Craig, and Alek dive deeper into episode 16, “Cupcake,” prompted by listener questions. They discuss how rare and satisfying it was to see Victoria choose her career over love, a choice echoed in Robin’s character arc as well. The team explores the value of fan theories—whether or not the creators intended certain meanings—and the power of unconscious storytelling, comparing it to dream logic, color theory, and even Hemingway’s deflection of symbolism. They reflect on the permanence of small writing decisions, the difficulty of letting go of a character like Victoria, and the seduction of career compromises in your late 20s, as embodied by Marshall and Barney’s plotline. They also dig into how “Cupcake” encapsulates the series’ core themes: timing, ambition, love, and missed chances.

Questions from Fans:

What do you think your role is now that you can respond to years of fan theories?

Is there value in correcting or affirming fan fiction and rumors?

Was Victoria ever planned to be the Mother if the show was canceled after Season 1?

Was it hard to let Victoria go as a character?

How long did it take before you realized Marshall and Barney working together was fun?

Can you describe the moment when you know a story decision is the right one?

Is “Cupcake” the emotional core of the series?

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We’ve got HWMYM merch, which is now just a FEW CLICKS AWAY.

CRAIG’S BOOK IS AVAILABLE FOR PRE-ORDER!

Head over to CRAIG’S WEBSITE to pre-order your copy of That’s Not How It Happened today.

And if you’re a business with big orders to fulfill, Amplifier is there to help growing consumer brands and influencers create a unique experience for their customers during the fulfillment process. Visit AMPLIFIER to learn more, and name-drop How We Made Your Mother for special pricing for your emerging brand's program.

CONNECT WITH THE SHOW:

Official Website (Send us your audio and written messages)

Substack (Join the mailing list, get announcements, and read more from Josh and Craig)

Instagram

HOW YOU MAKE A DIFFERENCE

Donate to our ongoing campaign to support congenital heart disease research

AND MORE:

Josh’s “Museletters” on Substack

Josh’s Official Website

Josh on Spotify

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

Alek’s “Dead Fathers Society” on Substack

Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this episode of How We Made Your Mother, Josh and Craig revisit “Cupcake” (Season 1, Episode 16), reflecting on the pivotal crossroads for Ted and Victoria as she prepares to leave for Germany. They praise Ashley Williams’s performance and discuss the episode’s unique structure—showing the same day from both characters’ perspectives. The conversation dives into how HIMYM grapples with adult issues like money, long-distance relationships, and self-identity in your 20s, highlighting the show’s emotional honesty beneath its humor. They explore Barney’s manipulative but needy attempts to recruit Marshall to the “dark side,” Lily’s cake-sitting disaster, and the subtle foreshadowing of relationship trouble through visual metaphors like ill-fitting suits and wedding dresses. A recurring theme is the tension between “I” and “we” in young relationships, with insight from a clinical psychologist (and Josh’s wife) about emotional development and timing. They end with a heartfelt listener letter about how HIMYM led one fan to the love of his life—and the perfect yellow umbrella.

GET YOUR MERCH!

We’ve got HWMYM merch, which is now just a FEW CLICKS AWAY.

CRAIG’S BOOK IS AVAILABLE FOR PRE-ORDER!

Head over to CRAIG’S WEBSITE to pre-order your copy of That’s Not How It Happened today.

And if you’re a business with big orders to fulfill, Amplifier is there to help growing consumer brands and influencers create a unique experience for their customers during the fulfillment process. Visit AMPLIFIER to learn more, and name-drop How We Made Your Mother for special pricing for your emerging brand's program.

CONNECT WITH THE SHOW:

Official Website (Send us your audio and written messages)

Substack (Join the mailing list, get announcements, and read more from Josh and Craig)

Instagram

HOW YOU MAKE A DIFFERENCE

Donate to our ongoing campaign to support congenital heart disease research

AND MORE:

Josh’s “Museletters” on Substack

Josh’s Official Website

Josh on Spotify

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

Alek’s “Dead Fathers Society” on Substack

THANK YOU TO OUR SPONSORS:

Mint Mobile - If you like your money, Mint Mobile is for you. Shop plans at mintmobile.com/yourmother

HelloFresh - Go to ⁠HelloFresh.com/YOURMOTHER10FM⁠ now to get 10 Free Meals with a Free Item For Life.

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In this General Questions episode, the team brings back Chris Harris (writer of the HIMYM episode “Game Night”) to answer fan questions and explore deeper elements of storytelling from the early seasons. They discuss how HIMYM balanced large, event-style episodes with character development, whether Chris was intentionally given “scope” episodes like “Subway Wars,” and how character traits (like Marshall’s love of games) were assigned in the show’s early, more flexible days.

They touch on the importance of continuity in a serialized sitcom, the organic nature of callbacks, and the evolving creative relationships between writers, actors, and the broader crew. They also reminisce about fan theories, including a popular one about who left Robin the welcome mat, and offer a behind-the-scenes look at the collaborative dynamics that shaped HIMYM’s signature tone and complexity.

Questions From Fans:

Can you talk about putting together the scope versus the character?

How did you decide how many episodes you and Carter would write and how many you would give away?

Were you planning ahead for continuity details, like Barney mentioning the Peace Corps before his backstory was revealed?

What was the inspiration for Marshall’s love of making board games? Was that knowingly a character trait you were building?

In the writers’ room, how did continuity work? Was it a hive mind, or did someone “own” the show’s memory?

Who gave Robin the welcome mat—Ted or Barney? (posed via fan questions)

GET YOUR MERCH!

We’ve got HWMYM merch, which is now just a FEW CLICKS AWAY.

CRAIG’S BOOK IS AVAILABLE FOR PRE-ORDER!

Head over to CRAIG’S WEBSITE to pre-order your copy of That’s Not How It Happened today.

And if you’re a business with big orders to fulfill, Amplifier is there to help growing consumer brands and influencers create a unique experience for their customers during the fulfillment process. Visit AMPLIFIER to learn more, and name-drop How We Made Your Mother for special pricing for your emerging brand's program.

CONNECT WITH THE SHOW:

Official Website (Send us your audio and written messages)

Substack (Join the mailing list, get announcements, and read more from Josh and Craig)

Instagram

HOW YOU MAKE A DIFFERENCE

Donate to our ongoing campaign to support congenital heart disease research

AND MORE:

Josh’s “Museletters” on Substack

Josh’s Official Website

Josh on Spotify

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

Alek’s “Dead Fathers Society” on Substack

Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this episode of How We Made Your Mother, Josh and Craig are joined by writer Chris Harris to reflect on the making of Season 1, Episode 15: “Game Night.” The trio breaks down the episode’s structure, the origin of Barney’s backstory, and how the writers constructed a compelling present-day story to balance the flashbacks. They talk about the decision to reveal Barney’s past as a heartbroken hippie and the challenges of maintaining both comedic pacing and emotional depth. Chris shares memories from the writers’ room, including how “Marshgammon” came to life, legal hurdles around parodying Monopoly, and Neil Patrick Harris’s incredible physical comedy (even while sick). They also discuss HIMYM’s early use of narrative flexibility—flashbacks, unreliable memory, evolving tone—which laid the groundwork for later storytelling innovations. A fan letter from the Faroe Islands brings the conversation full circle, reminding them how the show continues to offer comfort and connection to viewers around the world.

GET YOUR MERCH!We’ve got HWMYM merch, which is now just a FEW CLICKS AWAY.

CRAIG’S BOOK IS AVAILABLE FOR PRE-ORDER!Head over to CRAIG’S WEBSITE to pre-order your copy of That’s Not How It Happened today.

And if you’re a business with big orders to fulfill, Amplifier is there to help growing consumer brands and influencers create a unique experience for their customers during the fulfillment process. Visit AMPLIFIER to learn more, and name-drop How We Made Your Mother for special pricing for your emerging brand's program.

CONNECT WITH THE SHOW:Official Website (Send us your audio and written messages)Substack (Join the mailing list, get announcements, and read more from Josh and Craig)Instagram

HOW YOU MAKE A DIFFERENCEDonate to our ongoing campaign to support congenital heart disease research

AND MORE:Josh’s “Museletters” on SubstackJosh’s Official WebsiteJosh on SpotifyCraig’s Official Website (with links to his published writing)Alek’s “Dead Fathers Society” on Substack

THANK YOU TO OUR SPONSORS:

Quince: Get free shipping and 365-day returns at https://quince.com/yourmother

MeUndies: Support the show by going to meundies.com/yourmother and using my code YOURMOTHER to get 20% off your first order, plus free shipping.

Learn more about your ad choices. Visit podcastchoices.com/adchoices