Therapuss with Jake Shane

Session 105: Hilary Duff (November 6, 2025) – Episode Summary

Episode Overview

In this highly anticipated season finale, host Jake Shane welcomes actress and pop culture icon Hilary Duff for an intimate, lively, and deeply nostalgic conversation. The session delivers a mix of humor, vulnerability, and behind-the-scenes stories, tracking Hilary’s evolving career, personal growth, and the return to music after a decade-long hiatus. Fans of Lizzie McGuire, Duff’s 2000s films, and her new single “Mature” will discover fresh insights into Hilary’s teen stardom, motherhood, mental health journeys, and her ever-growing connection with fans.

Key Discussion Points & Insights

1. Reflections on the Past and Season Finale Vibes

• Jake expresses deep gratitude to listeners for two successful seasons and his awe at landing Hilary as a guest ([00:10]).
• Emotional note on the podcast’s growth and his excitement for “bigger and better things” in Season 3.

2. Lizzie McGuire and the Making of an Icon

• Hilary shares candid memories of filming The Lizzie McGuire Movie and performing “What Dreams Are Made Of” ([04:23]).

  “I don’t even remember recording that song. But I will say now I love it… It wasn’t technically my song, it was a Lizzie McGuire song.” — Hilary ([05:09])

• Distinction between recording music for herself vs. for Lizzie McGuire.
• On the whirlwind of sudden fame as Lizzie:

  “One weekend, Lizzie McGuire posters appeared at all the malls... all of a sudden, I got mobbed.” — Hilary ([13:10])

3. Pop Stardom and New Music

• The 10-year gap between albums: Hilary felt ready to reconnect with fans and channel adulthood into her music ([07:52]-[09:10]).

  “I just felt like I had a lot of... I can finally fill in the blanks and I’m ready to share with people and connect with them on the level of now.” — Hilary ([07:57])

• The creative journey behind her new single, “Mature,” and the interplay of nostalgia and growth ([31:58], [32:01]).
• Discussion about touring in her teens, the challenges, joys, and why she’d approach it differently today ([34:57]).

  “I had very little training, but I had these songs and I was just gonna go for it… It was just, like, really scrappy.” — Hilary ([34:57])

4. Acting, Identity, and "Outgrowing" Lizzie

• On transitioning from Lizzie McGuire to films like A Cinderella Story and Raise Your Voice ([12:13]).
• Letting go of the Lizzie persona and the differences from her later characters, esp. her role in Younger ([22:56]).

  “Kelsey had this confidence that Lizzie never had… she was a little bit more beast mode.” — Hilary ([22:56])

5. Disney Channel Legacy & Mentoring the Next Generation

• The Disney Channel formula and Hilary’s exhaustion after intense schedules ([16:36]).
• Brief interactions with younger Disney stars like Selena Gomez and Demi Lovato ([18:03]).

  “It’s been so fun to watch all of them pave their way and watch the journey.” — Hilary ([18:24])

6. Motherhood, Growing Up, and Finding Community

• Parenting in an era of screens and short attention spans ([19:00]).
• Challenges of early motherhood, making "mom friends", and redefining priorities ([47:28]).
• The evolution of confidence, friend groups, and the importance of editing relationships as Hilary reached her thirties ([71:17]).

7. Celebrity Culture: Then vs. Now

• Nightlife nostalgia: clubbing pre-social media, when privacy felt possible and phones weren’t everywhere ([60:13]-[64:53]).

  “Now you can curate your entire life how you want people to see it. You couldn’t do that back then.” — Hilary ([63:01])

• Celebrity tabloid culture, paparazzi, and the impact of sites like Perez Hilton ([61:46]).

8. Candid Fan Advice: “Tell Me What’s Wrong”

• Hilary and Jake answer fan questions about relationships, friendship, and personal growth ([51:22] onward).
• Thoughtful insights on advocating for your needs, finding new friends, handling falling-outs, and dealing with unsupportive parents re: mental health ([55:53]-[77:56]).

  “Our nanny… will join a pickleball group or... just find some things that you like to do and go join a group and it will expand your life.” — Hilary ([55:23]) “It’s okay to edit. Sometimes you have to friend cleanse. It’s okay.” — Hilary ([71:18])

9. Mental Health and Generational Change

• Open discussion about OCD, mental health stigma, and the progress in how openly people share now ([75:33]-[80:14]).

  “Even just one generation ago, it was really tough for people to talk about their problems and their imbalances.” — Hilary ([78:00])

10. The Return: “Mature” and the Music Video

• Hilary describes the concept for the “Mature” video—meeting her younger self and themes of self-acceptance, growth, and nostalgia ([81:18]-[82:56]).

  “Being where I am now, it's really nice to send love back to yourself, you know, that's gone through whatever it's taken you to get wherever you are.” — Hilary ([82:22])

Notable Quotes & Memorable Moments

• On Not Feeling Cool:

  “Jake, we haven’t spent that much time around each other. I never feel cool.” — Hilary ([14:22])

• On Navigating Fame Young:

  “There was before, and then there was after. And was that kind of a tent pole moment… or did it take some time?” — Jake
  “It was instant. It was really fast.” — Hilary ([16:04])

• On Performing in Clubs Before Social Media:

  “No phones. Yeah. We used to spend three hours getting ready to go out… and we wouldn’t go out until like, midnight.” — Hilary ([60:13], [60:34])

• On Friendship and Editing People Out:

  “It’s okay to edit. Sometimes you have to friend cleanse.” — Hilary ([71:18])

• On Parenthood and Gray Hairs:

  “I'm really pissed about getting gray hairs... It's happening. It's crazy. And I'm just not ready.” — Hilary ([45:11])

• On Being Direct with Friends:

  “If I had to do that, I was like, you have to just own it and be like, ‘I can't show up for you in this capacity right now. It feels overwhelming. I need some space.’” — Hilary ([71:50])

• On the Power of Generational Openness:

  “This generation being so forthcoming about their struggles… is giving such a comforting space for people that... aren’t on TV or aren’t... It’s them not feeling alone.” — Hilary ([78:00])

Important Segments (with Timestamps)

• Intro, Gratitude, and Hilary’s New Music (00:10–04:06)
• Lizzie McGuire Movie & “What Dreams Are Made Of” (04:23–06:41)
• Transition to Music, “Metamorphosis” Years (09:10–12:13)
• Stepping Outside Lizzie, “Cinderella Story” (12:13–14:47)
• Fame, Pressures, and Paparazzi Stories (13:10–18:40)
• Motherhood and Her Children’s Perception of Her Career (19:00–22:03)
• On “Younger” & the Unmade Lizzie Reboot (22:56–24:21)
• Touring Experiences & Granny Hobbies (34:57–36:56)
• Celebrity Culture: Then vs. Now (60:13–64:53)
• Advice Segment: “Tell Me What's Wrong” (51:22–77:56)
• Discussing OCD, Therapy, Generational Change (75:33–80:14)
• Making the “Mature” Music Video (81:18–83:22)
• Final Reflections and Takeaways (84:00–86:16)

Tone & Atmosphere

• Warm, irreverent, and deeply honest—a mix of nostalgia, humor, and self-reflection.
• Jake’s enthusiasm, fandom, and empathy balance perfectly with Hilary’s relaxed candor and mature insights.
• The episode moves easily from pop culture memories to serious personal topics, keeping a breezy yet meaningful flow.

Final Takeaways

• Hilary Duff’s journey mirrors the ups and downs of many who found fame young—her humility, humor, and clarity shine as she reconnects with music and fans, older and wiser.
• Listeners are treated to rarely heard “behind the scenes” moments from 2000s pop culture, plus valuable life advice.
• Jake’s “therapuss” approach draws out introspection, laughter, and genuine connection, ending the season on a high, heartfelt note.

Key quote to sum up the session:

“It’s really nice to send love back to yourself… that’s gone through whatever it’s taken you to get wherever you are.” — Hilary Duff ([82:22])