CHEERS! with Avery Woods

Episode: "rebuilding + rebirth | gigi gorgeous"
Air Date: February 2, 2026
Guest: Gigi Gorgeous

Episode Overview

In this warm and candid episode, host Avery Woods shares a glass of wine and a deeply open conversation with Gigi Gorgeous, the trailblazing beauty creator and transgender advocate. Together, they discuss Gigi’s journey from a pioneering online makeup artist to an influential voice for the trans community, her experiences growing up in a supportive family, the difficult process of coming out, resilience through personal rebirth after divorce, and practical advice for open, accepting parenting. With characteristic humor and authenticity, the conversation spans everything from social media toxicity to body confidence, family bonds, transition surgeries, and the reality of rebuilding one’s life.

Key Discussion Points & Insights

1. Early Days & Impact on the Beauty Community

• Gigi’s Start
  • Avery reflects on discovering Gigi online as one of the first “boys doing makeup,” and how it opened her eyes to the trans community.
  • Gigi shares the importance of humor and uniqueness in her early videos, like her “morning routine” parody — "just, like, silly." (02:38)
• Childhood and Family Acceptance
  • Growing up in Toronto with two brothers, Gigi reveals her first makeup experiments were her "dirty little secret."
  • Despite the initial secrecy, her brothers were always accepting: “My brothers would invite me out to hang with their friends… That’s a way to show love. Actions speak louder than words.” (04:06)
• Finding Community Online
  • The internet became a vital escape and source of connection: “There’s people out there like me. They’re just not in my real life.” (03:21)

2. Journey of Self-Realization and Coming Out

• Early Awareness of Identity
  • Gigi knew she was “different” from an early age, often expressing femininity in private and feeling pressure from society to hide it. (06:32)
  • Acknowledges the common experience where “a breaking point” leads to finally living authentically, sometimes later in life for some. (07:29)
• Family’s Reaction
  • Coming out as gay at 15: “My dad is… stoic, wanted to hold it together. My mom just, like, cried. But I get it now because she just wanted me to be safe.” (28:03)
  • She later came out as trans at 19, with varied family responses but ultimately acceptance from her brothers and, over time, her father.
  • On her mother: "She was always very accepting... but I think for her kid, it’s different; she just didn't want me to get beat up or bullied more." (28:59)

3. Navigating Social Media & Building Resilience

• First Platforms and Rise to Fame
  • Gigi started on MySpace before YouTube (2008): "I uploaded my daily makeup routine and put Rihanna's Disturbia behind it.” (23:02)
  • Early YouTube experience was isolating: “I felt very alone… there really was no community.” (23:59)
• Dealing with Backlash & Hate
  • Faced significant hate comments for being one of the first visibly queer beauty creators, but positive comments “gave me the confidence to come out.” (25:28)
  • She held onto the encouragement: “If you can change one person's opinion by sharing your story, then it's worth it.” (34:18)
• Changing Climate of Social Media
  • Both agree the environment has become “toxic,” but acknowledge the growth in acceptance and presence of LGBTQ+ identities online.
  • Gigi notes: “It is a responsibility to be trans… You don't sign up to be a teacher, but you kind of have to be that bitch who walks into a room and is like, hey, this is me.” (33:35)

4. Parenting, Gender, and Identity Education

• Avery’s Parenting Philosophy
  • Shares anecdotes about letting her son wear nightgowns and her careful approach to language and body image with her children.
  • Expresses her intention to raise open-minded and kind children: “I’m not gonna raise hateful kids. We need more kindness and empathy in this world.” (40:49)
• Gigi’s Advice for Discussing Trans Issues
  • Suggests starting from curiosity: “Do you guys know what trans is? Is there anybody in your class that identifies as trans?” (39:18)
  • Recommends a dialogue-based approach: “I would just ask them, and then... tennis match them. So why do you think this? Who do you know?” (41:21)
  • Stresses importance of not prescribing identity but letting children discover themselves.

5. Transition Surgery & Medical Realities

• Language/Education
  • Clarifies correct terminology: “It’s gender reassignment surgery or confirmation surgery.” (34:53)
• Personal Decision & Community Experiences
  • Gigi shares that she hasn’t had bottom (genital) surgery and has realized over time she’s happy with that choice:
    • “I would have regretted getting that surgery, because now I'm so happy that I did not…who’s to say, you know, down the line?” (36:00)
  • Expresses empathy for trans friends who regretted their surgeries due to complications: “It is life or death a lot of the time.” (38:02)
  • Hopes for better medical outcomes: “I just want it to be always 100% success rate, and that's obviously never…”

6. Rebuilding and Rebirth After Divorce

• Personal Upheaval
  • Gigi recounts her difficult divorce: “I was almost with my ex-husband for like ten years…It's like, you kind of have to relearn how to live.” (52:45)
  • Details mourning the loss and personal identity beyond the relationship: “Even in happy marriages, you can lose yourself… snap back.” (53:41)
• Moving Forward
  • Focuses on pouring energy “back into my cup” and embracing new projects and opportunities, even if currently under wraps.
  • On dating again: “It’s a lot different…Now I step into a room with my full chest—this is me.” (62:50)
  • Expresses possibility of love in the future but doubts about ever marrying again: “I've said before publicly, I will never get married again. That’s off limits. But...I love love so much.” (54:26, 55:03)
• Praise for Grace and Maturity
  • Avery commends Gigi for her grace and class in publicly handling her divorce:
    • “The respect I have for you for being so kind... you really handled it with such grace and class.” (58:44)

7. Industry Musings & Staying Grounded

• Beauty Community Culture
  • Gigi and Avery discuss the double-edged sword of the influencer world: “Once you find a few people, it’s cute, but for the most part, I just like the environment of creativity and people that are just, like, different.” (47:02)
  • Both prefer grounding themselves among friends outside the industry for humility and normalcy.
• On Humility and Kindness
  • Gigi: “People make it far because they are nice. I won’t ever understand why you’d act like they're below you.” (51:05)
  • The importance of kindness rings as a refrain throughout the episode.

Notable Quotes and Memorable Moments

• On the Power of Positive Influence
  • “You gave me the confidence to wear makeup to school today, gave me the confidence to start transitioning, whatever—for me, that made it worthwhile.” (25:28, Gigi Gorgeous)
• On Parental Support
  • “My brothers were always really accepting...That’s a way to show love. Actions speak louder than words.” (04:06, Gigi Gorgeous)
• On Authenticity
  • “In a way, you have to put on...Command the, you know, vibe of it all. You can't go in meek...No, you kind of have to put on your best face.” (33:26, Gigi Gorgeous)
• On Protecting Children’s Innocence Online
  • “When will they get, like, devices? For safety, yes, but social media...as long as I can hold off, I would say, because once you’re in, you’re in.” (17:23, Gigi Gorgeous)
• On Kindness in the Industry
  • “Will it kill you to be kind? I will never understand that.” (52:01, Avery Woods)
  • “People make it far because they're nice...I can't even imagine going through something that was very detrimental and we hated each other...that gives me peace.” (61:02, Gigi Gorgeous)
• On Rebirth After Divorce
  • “Now I’m focused on pouring back into my cup...It is like a process.” (54:12, Gigi Gorgeous)
  • “It is like divorce is like death… you're mourning someone who's alive.” (56:59, Gigi Gorgeous)
• On Parenting and Gender
  • “I want them to discover that on their own…if you tell me something that I should think that way, I will challenge it and probably think my own way.” (41:26, Gigi Gorgeous)
• On Survival and Legacy
  • “We walked so they could run.” (30:31, Gigi Gorgeous)
• Lighthearted Ending
  • On a possible future dating show: “Should I do a dating show? Gigi’s new boyfriend...” (62:14, Gigi Gorgeous)
  • “They’re sitting pretty and they’re here to stay. I’m done. Come on, Garth Fisher.” (63:31, Gigi Gorgeous)

Important Timestamps

• Gigi’s Childhood and Sibling Support: 03:12—04:32
• Coming Out Experiences: 27:19 (gay at 15), 31:47 (trans at 19)
• Social Media Rise and Impact: 23:02—25:28
• Parenting Approaches & Discussion of Gender: 39:08—41:56
• Transition Surgery and Regret: 34:53—37:22
• Divorce and Personal Rebuilding: 52:26—61:47
• Dating Again & Life After Divorce: 61:55—64:39

Tone and Takeaways

The episode maintains a conversational, humorous, and nurturing tone. Both Gigi and Avery are unfiltered but always kind, moving fluidly between laughter and vulnerability, and never shying away from the difficult realities of both online life and deeply personal transformation. Standout themes include the importance of living authentically, the critical impact of a loving support system, and the vital need for ongoing empathy and kindness—both online and off.

Find Gigi Gorgeous:
"I am Gigi Gorgeous everywhere. And, yeah, just Google me." (68:08)

Closing Cheers:
"Cherish every phase, own your truth, and remember—actions (and kindness) speak louder than words. Cheers!”