Podcast Summary

Podcast: BFFR with Sydney Leroux & Ali Riley
Episode: Lilly Singh on Her New Movie Doin’ It, Investing in Angel City & Supporting Women
Date: October 13, 2025
Hosts: Sydney Leroux & Ali Riley
Guest: Lilly Singh

Overview

In this energetic and candid episode, Ali Riley (co-hosting solo this week) sits down with comedian, creator, and trailblazer Lilly Singh. The conversation ranges from Lilly’s groundbreaking feature film "Doin’ It," her vital role as an investor in Angel City FC, breaking taboos and stereotypes around sex education, supporting women, mental health practices, and the realities of life, love, and dating as a public figure. Expect honest insights, laughter, and heartwarming exchanges as these two friends explore vulnerability, identity, and female empowerment.

Key Discussion Points & Insights

1. Lilly Singh’s Journey with “Doin’ It”

• Seven-Year Creative Process
  • The movie took 7 years to create, healing many personal issues for Lilly, including her discomfort around open conversations about sex.
  • “I did it for little Lilly and I did it for other people. Honestly, it has healed so many parts of my sex self… I never used to be able to say the word sex before shooting this movie.” — Lilly Singh (05:28)
• Plot and Significance
  • The film is a sex comedy about Maya, a reserved, 30-something virgin forced to teach sex ed to teenagers, holding a comedic mirror to the failures of current sex education, especially for women and people of color.
  • “It’s a commentary on sex education, it’s a commentary on women, and learning, shame—but you know, it’s mixed in with a bunch of sex jokes, which I think comedy is the best vehicle for.” — Lilly Singh (07:24)
• Family Reactions
  • Lilly was nervous for her parents to see the film, given its explicit content.
  • Her father’s open-minded reaction: “He was like, honestly, Lilly, I thought it was really good… I learned a lot from it.” — Lilly (10:15)
  • Making the movie allowed for more open family conversations about sex, helping to heal generational taboos.

Notable Moment

“If that can happen for people that watch the movie, that would be really cool.” — Lilly (11:49)
(On families having conversations about sex after watching the film)

2. Representation, Producing, and Barriers in the Film Industry

• Necessity of Representation Behind the Scenes
  • Lilly underscored the critical importance of being a producer on her own movie to avoid cultural insensitivities:
  • Hilarious anecdote about ensuring a prosthetic used on set was realistic for a South Asian man, resulting in a “penis mood board.”
  • “If I wasn’t a producer, Utkarsh would have a pink penis… I need to fight for every single thing, every step of the way.” — Lilly (16:44)

3. Investing in Angel City FC and the Power of Women in Sport

• How Lilly Became an Angel City Investor

  • Approached because of her work supporting women and girls; she had no background in soccer but a deep commitment to women’s empowerment.
  • “People always are like, did you grow up playing soccer?... I don’t need to know the rules. I will blindly support girls and women.” — Lilly (19:03)

• Impact and Community

  • Lilly emphasized that investing in girls and women yields the greatest return for communities worldwide.
  • Describes Angel City games as the “Gay Met Gala”—a space of inclusion, pride, warmth, and joy.
  • “It is one of the most inclusive, positive sporting environments I’ve ever been to.” — Lilly (21:54)

Notable Quotes

“I have a rule: If anyone is performing, in any capacity… they’re gonna get 100 of this energy.” — Lilly (20:30)

“Everyone I bring, they’re all like—this is such a positive, just warm environment.” — Lilly (22:54)

4. Lilly’s Broader Investments and Personal Motivations

• Toronto Tempo and Beyond
  • New part-owner of Canada’s first WNBA team, the Toronto Tempo.
  • “Women in sports, women in sports.” — Lilly (28:03)

5. Reflections on Career & Identity

• From “Superwoman” to Lilly Singh

  • Reflects on her early YouTube days as “Superwoman”—a name born from a song and a desire to feel empowered.
  • Transitioning to using her real name symbolized personal growth and true self-acceptance.
  • “That was the first time in my life I felt more empowered being called Lilly than Superwoman.” — Lilly (34:25)

• Balancing Work and Wellness

  • Early career was all “hustle” with little thought to physical or mental health.
  • Now prioritizes boundaries, morning rituals, and mental routines.
  • “My job is like 20% acting... 80% is just making sure my mind is right.” — Lilly (31:10)

Self-Care Practices

• No meetings before 10am; mornings are for self, reflection, and grounding.
• “I have three hours to make myself tea, cuddle with my dogs, journal, stretch, pray, meditate, be, eat breakfast, take a shower—just be a full human.” — Lilly (31:42)

6. Friendship, Community, and Social Life

• Highly Structured Social Calendar
  • Lilly’s dedication to friendship is “type A,” scheduling monthly time with friends to ensure community doesn’t fall to the wayside amid work.
  • Critiques LA’s culture of “flakiness”: “People are way too comfortable with dismissing their flakiness as self-care, and those two things are not the same.” — Lilly (41:42)

7. Dating as a Public Figure

• Challenges & Insights
  • Dating is “harder” as a celebrity, often due to safety, privacy, and not being able to share fully with prospective partners.
  • Only uses Raya (industry-invite dating app), which is both helpful and restrictive.
  • “Everything I feel or want to say has to go through a filter of some sort, and it makes it really tough to have an authentic, genuine connection.” — Lilly (47:22)
• Best Date Story
  • Recalls a sweet moment when a date remembered her favorite drink—“acts of service, small things.”
  • “Maybe my bar is in hell, I don’t know. But that was really, really sweet.” — Lilly (49:19)

8. Advice Segment: Audience Questions

Relationship & Dating Advice

• Communicating About Intimacy
  • Advice for a listener with a “bad kisser” boyfriend: Use positive, playful direction to guide intimacy rather than negative feedback.
  • “I believe when it comes to intimacy… there’s a very lighthearted way to address things.” — Lilly (50:46)
• Long-Distance Relationships
  • Emphasizes the importance of intentional communication and proactively planning visits to maintain the spark.
  • “Get that side hustle, book those flights… The real advice I have for you is you both need to commit to making that side bag.” — Lilly (52:18)
• Finding Love at Angel City Games
  • Encourages listeners to put themselves out there: “I feel like you could literally hold up a sign saying looking for a date… No one would judge you.” — Lilly (54:29)

Memorable Moments & Quotes

On Meaningful Representation

• “When we talk about battles I wasn’t prepared for, it’s things like this. If I wasn’t a producer… Utkarsh would have a pink penis… I need to fight for every single thing.” — Lilly (16:44)

On Feeling Seen & Creating Change

• “What you said about wishing a movie like this had been made sooner is very similar to how I feel about Angel City and this league. We are making a difference.” — Ali (09:36)

Heartfelt Friendship

• “You are something special… You have this magnetic energy that just makes people feel really, really good… I will cheer you on just the same in whatever you do.” — Lilly (55:15)

Timestamps for Key Segments

• [03:16] Introductions and checking in
• [05:28] Lilly details the journey and personal impact of making "Doin’ It"
• [07:24] Explaining the film’s plot and purpose
• [10:15] Family reactions and importance of breaking generational silence
• [13:24] Producing, representation, and “penis mood board” story
• [19:03] How Lilly became an Angel City investor and why women in sport matter
• [21:54] Angel City’s unique, inclusive atmosphere
• [28:30] Reflecting on the evolution from YouTube to today
• [31:42] Importance of self-care, morning routines, and mental health
• [41:42] LA’s flakiness vs. real friendship; social calendar strategies
• [45:40] Dating as a celebrity, using Raya
• [49:19] Sweetest date experience
• [50:24] Relationship advice segment
• [52:18] Advice on long-distance love
• [54:29] How to find a date at an Angel City game
• [55:15] Lilly’s heartfelt message to Ali on retirement
• [57:23] Closing remarks

Tone and Style

The episode is a blend of hilarious, unfiltered commentary, heartfelt confession, and candid insight. The camaraderie between Ali and Lilly makes for warm, uplifting listening, peppered with the sort of practical wisdom and playful banter that defines the BFFR podcast.

Final Thoughts

This episode is essential listening for anyone interested in representation in media, women’s sports, comedic storytelling, friendship, and the power of vulnerability. Lilly’s honest reflections on creative risk, investing in women, and personal growth deliver inspiration and plenty of laughs, while Ali provides warmth and thoughtful connection throughout.

For full laughs, inspirational moments, and real talk about doing it all as a woman and a friend, listen to the full episode wherever you get your podcasts.