Podcast Summary: Introducing How We Made Your Mother Season 2!

Podcast: Jill on Money with Jill Schlesinger
Date: November 1, 2025

Episode Overview

In this special crossover announcement, Jill Schlesinger departs from her typical financial topics to spotlight the beloved sitcom How I Met Your Mother and introduce fans to the return of its official rewatch podcast: How We Made Your Mother Season 2. Hosted by series star Josh Radnor (Ted Mosby) and creator Craig Thomas, the podcast promises behind-the-scenes stories, thoughtful analysis, and fan engagement as they revisit and dissect the show’s key moments, characters, and legacy.

Key Highlights and Discussion Points

Introduction to the Rewatch Podcast

• Jill Schlesinger (00:00):
  • Sets a nostalgic tone, inviting listeners who loved How I Met Your Mother (HIMYM) to join an insider journey behind the scenes.
  • "The stakes are higher, the stories are deeper, and yes, the pineapple mystery still comes up."
  • Distinguishes the podcast as an immersive experience: "Sitting in the writers room minus the deadlines."
• Encourages listeners to take a break from finance talk and enjoy the fun recaps.

Meet the Hosts and Mission

• Josh Radnor (01:09):
  • Introduces himself as “Ted Mosby, the ‘I’ in How I Met Your Mother,” joined by creator Craig Thomas.
  • Outlines the format: an episode-by-episode reflection on the show.
• Craig Thomas (01:31):
  • Marks major anniversaries: "Somehow it has been 20 years since the show premiered... Ten years since it went off the air."
  • Emphasizes the motivation: examining why the show endures worldwide.

New Network and Community Vibes

• Josh Radnor (01:47):
  • Announces the podcast joining the Office Ladies Network, collaborating with Jenna Fischer and Angela Kinsey from The Office’s rewatch podcast.
• Jenna Fischer & Angela Kinsey (01:58):
  • Express delight at welcoming Josh and Craig:
    • "Something we love about How We Made Your Mother is the amazing community... the fans and people that write in—they are awesome."
  • Highlight the mix of fun and depth, including philosophical musings.

The HIMYM Storytelling Magic

• Angela Kinsey (02:12):
  • Praises the hosts' ability to “get philosophical”—delving into love, friendship, and forgiveness alongside the comedy.
    • "Josh suddenly starts quoting Einstein or some ancient philosopher. And then he and Craig basically break down the meaning of love..."
• Josh Radnor (02:33):
  • Recalls emotional highlights from season one of the podcast:
    • "I was so into him being with Robin when he goes up in the suit... really quite sexy for primetime."
• Behind-the-Scenes Humor (02:51):
  • Ashley Williams describes setting boundaries during on-screen kisses:
    • "Every time we kissed, I would go—like, I had, like, hard... the only way I can describe it... hard lips."
  • Josh humorously:
    • "You're kissing me weird, right? I think that's all I was saying." (03:26)

Generational Relatability

• Cobie Smulders (03:32):
  • Observes the show’s cross-generational appeal:
    • "There are people who are our age who are like, I remember being in my 20s watching this show... And then I'll meet somebody who's like, 15. I'm like, you were not alive."

Teasing Season 2 Guests & Surprises

• Josh Radnor (03:50):
  • Reveals exciting upcoming interviews, including:
    • Joe Manganiello
    • Bryan Cranston
• Bryan Cranston (04:11):
  • On knowing a show’s future:
    • "Whether it's How I Met Your Mother, whether it's Breaking Bad, the question we always get asked is, did you know it was going to be a hit? No one ever knows. But what you do know... is that it was good."

Fan Involvement and Global Community

• Craig Thomas (04:26):
  • Invites fans to interact via their website, sharing messages, emails, and stories—many of which are featured in episodes.
• Fan Montage (04:36):
  • Diverse fan voices from around the world—Florida, the UK, Brazil, Colombia, the Netherlands, Bulgaria, India, Chile, Estonia, Bosnia, and more—express thanks and connection.
• Craig and Josh (closing):
  • Thank fans for their support and emphasize their charitable initiative supporting congenital heart disease research for children (05:00).

Call to Action

• Josh & Craig (05:04):
  • Encourage subscriptions and regular listening:
    • "Follow and listen to How We Made Your Mother wherever you get your podcasts."

Notable Quotes & Memorable Moments

• "The stakes are higher, the stories are deeper, and yes, the pineapple mystery still comes up." — Jill Schlesinger (00:05)
• "Somehow it has been 20 years since the show premiered... Ten years since it went off the air." — Craig Thomas (01:31)
• "Josh suddenly starts quoting Einstein or some ancient philosopher. And then he and Craig basically break down the meaning of love..." — Angela Kinsey (02:12)
• "You're kissing me weird, right? I think that's all I was saying." — Josh Radnor (03:26)
• "There are people who are our age who are like, I remember being in my 20s watching this show... And then I'll meet somebody who's like, 15. I'm like, you were not alive." — Cobie Smulders (03:34)
• "Did you know it was going to be a hit? No one ever knows. But what you do know... is that it was good." — Bryan Cranston (04:11)
• International fan montage: Warm global community spirit (04:36–04:56)

Timeline of Key Segments

| Timestamp | Segment | |-----------|---------| | 00:00–01:09 | Jill’s introduction and pitch for the HIMYM rewatch podcast | | 01:09–01:46 | Josh Radnor and Craig Thomas introduce themselves and the podcast’s mission | | 01:47–02:33 | Announcement of joining Office Ladies Network; community shout-outs | | 02:33–03:50 | Hosts discuss favorite moments, on-set anecdotes, and generational relatability | | 03:50–04:26 | Teasers for upcoming season and interview guests | | 04:26–04:56 | Fans worldwide share their appreciation; invitation for interaction | | 04:57–05:11 | Closing remarks, charity plug, and how to subscribe |

Tone & Language

Reflective, warm, humorous, and welcoming. The banter and affection among cast and creators shine through, matched by Jill’s lighthearted bridge from finance to fan culture.

Summary

For both devoted HIMYM fans and new listeners, this preview episode of How We Made Your Mother Season 2 blends cast insights, fan energy, and a promise of both laughter and thoughtful discussion. Listeners are invited not just to revisit the show, but to become part of an international community—and to expect legendary entertainment in every episode.