Work in Progress with Sophia Bush: Lilly Singh (Aired September 10, 2025)

Overview

In this dynamic and heartfelt episode, Sophia Bush sits down with her friend, comedian, author, producer, and changemaker Lilly Singh. The conversation oscillates between deep personal insights and playful banter, exploring themes such as the art of true human connection, healing inner child wounds, the value of storytelling, gender equity, representation in Hollywood, and Lilly’s mission to dismantle shame—particularly around sex and taboos.

Much of the episode centers around Lilly’s new film “Doom In It,” which serves as both an entertaining sex comedy and a personal, cultural intervention. The dialogue is open, vulnerable, and purpose-driven, interspersed with laughter and pragmatic life strategies.

Key Discussion Points & Insights

1. The Art of Connection & Presence

• Press Tour with Intention

  • Lilly describes her “era of connection,” aiming for real conversations on every stop of her press tour rather than superficial interactions. (06:19)
  • Lilly Singh [06:19]: “I’m here. I’m doing a little bit of a press tour for my movie, but I’m committed to enjoying every single second of it...just have good conversations and genuinely connect with people and be present.”

• Friendship in Hollywood

  • Both lament the rarity of genuine friendships in their field, where meaningful talk often loses out to small talk at big events.
  • Sophia Bush [12:02]: “I’m always in the corner having a deep talk with someone and then like, my agent yells at me and says I didn’t do my job. And I’m like, yeah, I didn’t go meet 18 producers. Cause I was learning about someone’s inner child.”

2. Inner Child Work, Rituals, and Healing

• Facing Trauma & Rewriting the Narrative

  • Lilly discusses her ongoing therapy and “inner child work,” describing how shifting her attitude from blaming her younger self for her adult wounds to celebrating her resilience has been transformative.
  • Lilly Singh [10:35]: “For most of my life, it’s been so painful to look at that little girl...Over the past couple months, I have really switched that narrative to be like, actually I have everything I have because of that little girl...So I’ve completely flipped the narrative to be like, thank you, little girl.”

• Practical Rituals

  • Lilly shares tangible rituals, like dancing to a song with her inner child before big events.
  • Lilly Singh [12:05]: “Before an audition...I always take a moment for that inner child. And I have a song that I play that I dance with her in...I dance with that little girl and I protect her.”

• Control and Pragmatism

  • Both women unpack eldest daughter/only-daughter syndrome and the urge to control chaos through lists, structure, and rituals.
  • Lilly Singh [13:17]: “The too long don’t read is control freak...I fully own my control freakness.”

3. Storytelling as Healing and Power

• How TV and Movies Modeled Humor and Life

  • Lilly shares about being “raised by The Simpsons and Fresh Prince” and how TV crafted her comedic instincts and emotional understanding.
  • Lilly Singh [15:01]: “I was raised by the Simpsons. A lot of my humor comes from the Simpsons...it’s how I understood myself and the people around me.”

• Comedy as Medicine

  • Both agree storytelling is a powerful intervention (“It’s the medicine”—Lilly [16:30]) and discuss how narrative shapes the way people view themselves and social systems, including gender.
  • Sophia Bush [17:06]: “Everything is a story.”
  • Lilly Singh [16:46]: “It’s made up. Everything is made up.”

4. Navigating Age, Self-Rediscovery, and Liberation

• Sophia’s 40s “Death and Rebirth”
  • Sophia opens up about feeling more confident, happy, and alive in her 40s than any prior decade.
  • Sophia Bush [27:35]: “I turned 40, I had like a complete death and rebirth of the soul...there’s nobody meaner to me than me...But honestly, I’ve never felt cuter. My style has never been better. I’ve never had better sex. I’ve never had better relationships.”

5. Gender Equity, Sports, and Social Investment

• Lilly’s Involvement with Angel City, Toronto Tempo, and Investing in Girls

  • Lilly details her investments in women’s soccer teams as strategic moves to uplift girls and women, citing sports’ transformative power, especially in India.
  • Lilly Singh [28:58]: “The greatest investment you can actually make is in girls and women. There is no greater return on investment. And I’ve seen it firsthand.”

• Representation with Purpose

  • Both highlight the ripple benefit of girls’ advancement for entire communities, including boys.
  • Lilly Singh [30:11]: “It is actually factually and statistically true that if you invest in girls, the whole world will benefit.”

6. Embracing Cultural Diversity and Challenging the Mainstream

• The Privilege of Exposure
  • Lilly and Sophia reflect on growing up with diverse communities and cultures in Toronto and LA, and the privilege that brings.
  • Lilly speaks passionately about not letting Hollywood box her culture as “niche” and actively showcasing her Indian-Canadian heritage.
  • Lilly Singh [37:24]: “I just got beaten down over years...which is why I now so proactively go out of my way to be like, no, my culture is really cool.”

7. Creating “Doom in It”: A Sex Comedy as Cultural Intervention

• Personal and Cultural Healing

  • The film incorporates nods to Lilly’s upbringing and her mother’s, with her mom serving as a cultural consultant to ensure authenticity.
  • Lilly Singh [45:37]: “My mom is actually factually the cultural consultant on the movie...Anytime there’s Punjabi or Hindi, my mom’s making sure we say it right.”

• Dismantling Shame—Onscreen and Off

  • The film unapologetically addresses sex taboos, aiming to liberate women from shame and awkwardness through humor and honest storytelling.
  • Lilly Singh [48:51]: “I wrote it with one thing in mind, which was this is gonna be a completely unapologetic love letter to girls and women who have just felt shame around this subject their whole life.”
  • Discusses fighting to keep in jokes about tampons, pubic hair, and the importance of not sanitizing conversations that matter.

• Healing Across Generations

  • Making the film sparked conversations with her own mother she never anticipated—and even led to her mother making sex jokes on set.
  • Lilly Singh [50:07]: “We try to talk about those nuances in this film a lot. But, yeah...I never got the talk. Growing up, me and my mom had to talk for the first time during this movie.”

• Practical Tools for Unlearning Shame & Finding Liberation

  • Safety (reassuring oneself with “I am safe” prompts)
  • Listing out all life’s options to remind oneself of agency
  • Dedicating a day just to operate out of “what do I actually want?”
  • Lilly Singh [54:31]: “Just to remind yourself that you actually have the freedom to do whatever the hell you want.”

8. Hollywood, Representation, and The Real Table-Building

• On Building New Tables and Real Representation

  • Lilly is clear that true representation means more than tokenism; it’s about handing the mic to those who live the experience, resisting homogenization, and valuing specificity over palatability.
  • Lilly Singh [61:38]: “I want stories to be told from the people experiencing those stories. And I want to create a system where...I don’t want notes that make my stories more palatable for people because they don’t have that experience.”
  • Sophia underscores that specificity, not “vanilla-izing,” is what compels audiences.

• Diversity Is Profitable

  • Lilly Singh [62:55]: “Every time diversity does really well, it’s an exception. The Barbie movie. Black Panther. It’s like, no, people want diversity. If you look at the box office numbers...they’re the ones that are driving the box office.”

9. Unicorn Island: Lilly’s Production & Philanthropy Mission

• Unicorn Island Productions & Fund

  • Unicorn Island aims to change how girls and women are valued globally through storytelling and culture change, de-weaponizing shame.

  • Lilly Singh [65:44]: “One of the greatest injustices is that 50% of the world population doesn’t get the opportunity, doesn’t have the rights...It makes no sense, no matter how you look at it, to not give girls and women the opportunities...And so Unicorn Island is all about: how do we change the culture around how girls and women are treated?”

  • Tells the story of a real-world Indian village soap opera that changed attitudes and delayed child marriage—proof of storytelling’s power.

10. Gender Equity Benefits Everyone

• Liberating Men and Boys Too
  • Both highlight how gender equity and dismantling the patriarchy liberates men from restrictive roles and emotions.
  • Lilly Singh [70:11]: “...if you really think that the patriarchy and the stuff doesn’t impact you, like, I want you men to reflect on every moment. You feel so stressed and anxious because you are just burdened with expectations of...can’t talk about your mental health...all of that is the patriarchy.”

11. “Work in Progress”: Identity Beyond Achievement

• Lilly’s Ongoing Journey
  • Her real work in progress? Remaining a student for life, valuing growth and self-awareness above accolades.
  • Lilly Singh [72:57]: “My work in progress is always going to be my mind and my spirituality and my growth.”

Notable Quotes & Memorable Moments

• On Flipping Your Trauma Narrative
  “Actually I have everything I have because of that little girl...So I’ve completely flipped the narrative to be like, thank you, little girl.” — Lilly Singh [10:35]

• On the Power of Story
  “I really do believe in the power of stories. And I first and foremost call myself a storyteller for that reason.” — Lilly Singh [17:12]

• On Investing in Women
  “There is no greater return on investment...When you invest in a girl, she goes to school and then her family benefits.” — Lilly Singh [28:58–30:07]

• On Representation in Hollywood
  “They want unique points of view and unique characters, but we’re going to give you all these notes to turn them into a generic, watered down version of that...I don’t want notes that make my stories more palatable for people.” — Lilly Singh [61:38]

• On Gender Equity
  “When we talk about gender equity, we’re also talking about liberating men and boys in a very, very real way.” — Lilly Singh [70:44]

• On Work in Progress
  “My work in progress is always going to be my mind and my spirituality and my growth.” — Lilly Singh [72:57]

• Humorous Highlight

  • On Sophia’s sex life:
    “Say it again. Sophia Bush is having the best sex of her life. You heard it here, y’all. This is the clip—editors, if you want the viral clip for the socials...” — Lilly Singh [51:58]

Timestamps for Key Segments

• The Value of True Connection: 06:07–07:37
• Inner Child Work & Rituals: 08:40–12:30
• Storytelling as Intervention: 15:01–17:44
• Pragmatism & Control: 13:16–14:23
• Cultural Diversity in Upbringing: 36:06–39:35
• Investing in Girls and Women, Sports: 28:31–32:50
• Building Unicorn Island & Changing Culture: 64:40–67:56
• Dismantling Shame with Comedy and “Doom In It”: 45:27–51:36
• Liberating Men & Gender Equity: 68:36–72:26
• Lilly on Identity & Growth as a ‘Work in Progress’: 72:57–74:07

Final Thoughts

This episode is a masterclass in vulnerability, wit, and activism through storytelling. Both Sophia and Lilly model the kind of authentic, non-performative dialogue they wish for the world—one where trauma is transformed into strength, where culture and identity are sources of pride, and where laughter and pragmatism are powerful tools for healing.

Lilly’s new film, “Doom In It,” epitomizes her mission: dismantle the shame around sex, amplify marginalized voices, and do it all with honesty and humor. Whether discussing inner child work, the power of specificity in storytelling, or why equity benefits all, this conversation is as rich and layered as the women at its center.

Highly recommended for anyone interested in cultural change, personal growth, or just a damn good conversation.