How We Sat on a Cake | S1E16 "Cupcake"

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