Podcast Summary: Long Winded with Gabby Windey

Episode: The Robby Hoffman
Date: December 18, 2025
Host: Gabby Windey
Guest: Robby Hoffman

Episode Overview

This episode sees Gabby Windey in conversation with her wife, comedian and Emmy-winning writer Robby Hoffman. The conversation is an intimate, witty, and heartfelt deep dive into career milestones, their relationship, creative process, family history, resilience, art in the age of AI, and the joys and struggles of growing up and "making it"—with plenty of self-aware humor and warmth. Central to the episode is the celebration of Robby's new Netflix stand-up special ("Wake Up," directed by John Mulaney, out December 14) and reflections on authenticity, ambition, partnership, and pride.

Major Topics & Key Discussion Points

1. Introducing Robby & Setting the Tone (03:00–04:15)

• Gabby introduces Robby with a loving, comedic list of credits—Emmy-winning writer, actor on "Hacks," and most importantly, her wife.
• Robby jokes about being nervous recording in Gabby's Colorado hometown, praising the cozy home studio and referencing the cold and altitude.

2. The Realities of Distance & Relationship Dynamics (06:25–08:40)

• Both discuss what it’s like to spend significant time apart due to their careers, including long-distance between Toronto (for Gabby’s Netflix project) and other cities (for Robby’s tour).
• Gabby notes: “The worst part is when you’re not there and I look over and your side of the bed is empty.” (07:37)
• Robby shares the ongoing joke about their dog Nardo filling the gap at home.

3. Coping with Altitude and Vices (08:50–10:30)

• Gabby teases Robby’s obsession with canned oxygen for altitude sickness, calling it “placebo,” while Robby defends it as a cheap, practical hack.
• “I always say I do not trust people without a vice. Whether her vice is the oxygen or the vape, either way…” —Gabby (00:45)

4. Inside Robby’s Netflix Special: “Wake Up” (10:44–26:52)

a. Aesthetic & Creative Choices (10:44–14:10)

• Gabby expresses genuine pride and emotion watching Robby’s special, praising its cinematic intro, careful decisions, and overall “chic” vibe.
  • “I cried at the intro because I’m just like, so proud of you.” —Gabby (10:30)
  • “There’s really nothing that special about it except that it’s just… good.” —Robby (13:55)
• Robby highlights her philosophy: No gimmicks—“just good,” leading with heart and simplicity.

b. Career Journey + Integrity (12:10–26:27)

• Robby reflects on being a “slow and steady wins the race” type; her special felt earned, not rushed.
  • “The special just feels like I’m walking into my apartment. Like I’m walking home.” —Robby (15:41)
• She notes her refusal to cater to late-night TV’s demands for a sanitized five-minute set, holding out for opportunities that allow full honesty and creative integrity.
  • “I got to say it how I got to say it. I can’t be reading off your prompter and doing this.” —Robby (24:30)
• Netflix gave her “no notes,” letting her perform authentically.

c. Reflections on Risk and Artistic Bravery (26:52–29:52)

• Robby recounts the leap from a reliable day job to pursuing stand-up with “nothing to fall back on”—taking creative risks as a necessity and form of self-respect.
  • “You don’t get to just, like, take a risk creatively… I did have a lot to lose.” (28:24)
• Full-circle validation includes not just the Netflix spot but also being invited to late-night couches and being interviewed for her own special without having to “dance for her food.”

5. Artistic Authenticity in the Age of AI (17:24–20:51)

• Discussion on fears surrounding AI and how existential threat could spark a “renaissance” of human-created art.
  • “Some of the last art, as if to say we were here.” —Robby (18:33)
• Both believe that despite technological advances, art needs “heart and soul”—which only humans can create.

6. Family History & Growth (30:13–44:44)

• Robby tells emotional and funny stories from her childhood—sharing cake mishaps, growing up poor, and the deep kindness of her Uncle Eddie, who housed her family during hard times.
  • “We move in on a moment’s notice, middle of the year. Supposed to be temporary. My great uncle ended up dying in that house.” (40:29)
• She reflects regret at childhood rudeness to Uncle Eddie but redeems herself by later caring for him when he was ill.
  • Memorable moment: Robby describing the moment she put ointment on her uncle’s neuropathic feet—choosing to see the human in front of her. (35:07–36:31)
• Parallels drawn between caring for Uncle Eddie and later hand-feeding their dog Nardo when he was sick.

7. Birthday Surprises & Vintage Shopping (46:39–53:06)

• Gabby surprises Robby with a “Bachelor-style” private shopping spree at Robby’s favorite secondhand shop, BSB Consignment.
  • “I remember having a dream... a bike would go by and I could just grab it... That’s what this birthday surprise felt like.” —Robby (47:19)
• Discussion about their dynamic when vintage shopping—how it always starts as “all about Robby” but Gabby inevitably finds treasures for herself too.

8. The Evolution and Power of Vintage & Secondhand (56:07–58:48)

• Robby gets real about growing up shopping at Canadian Goodwill (Value Village), how it once brought her shame but now is a source of pride and self-expression.
  • “Now it’s come full circle where I only—everything I’m wearing is secondhand.” —Robby (57:54)
  • “Poverty is an epidemic and it’s only worsening. And I speak to it now and I don’t have shame.” —Robby (58:11)

9. Friendship, Gossip, and Social Spaces (60:27–63:51)

• Gabby raises the topic of gossip as communal fun and essential female bonding—making a case against shaming women for enjoying it.
  • “The best thing about if you have a 9 to 5, your only saving grace… is talking about the other people stuck there with you.” —Robby (62:11)
• Asserts the importance of “safe space” gossip (not online, not malicious) for well-being.
  • “Keep it. Close the door. Get a bottle of wine. Get cozy on some pillows... This is a safe space.” —Gabby/Robby (63:15–63:32)

Notable Quotes & Memorable Moments

• “I always say I do not trust people without a vice. Whether her vice is the oxygen or the vape, either way…”
  — Gabby (00:45)

• “I cried at the intro because I’m just like, so proud of you.”
  — Gabby (10:30)

• “I think to just do good is very difficult. Some people rely on gimmicks… But just by leading with heart and simplicity.”
  — Robby (13:24)

• “Some of the last art, as if to say we were here.”
  — Robby (18:33)

• “The worst part is when you’re not there and I look over and your side of the bed is empty.”
  — Gabby (07:37)

• “Poverty is an epidemic and it’s only worsening. And I speak to it now and I don’t have shame. I’m shamed about everybody else… That is what’s shameful. Not the fact that I was born poor.”
  — Robby (58:11)

• “The best thing about if you have a 9 to 5, your only saving grace, your only silver lining, is talking about the other people stuck there with you.”
  — Robby (62:11)

Important Timestamps

| Timestamp | Segment | Notes/Highlights | |-----------|------------------------------------------|--------------------------------------------------------| | 03:00 | Gabby’s playful intro of Robby | Sets intimate, irreverent tone | | 06:25 | Distance + relationship struggles | Tender moments about missing each other | | 08:50 | Canned oxygen anecdote | Humphorous take on vices and wellness trends | | 10:44 | Discussing the new Netflix special | Gabby gets emotional about Robby’s accomplishments | | 13:24 | “Just do good” philosophy | Robby on rejecting gimmicks, leading with heart | | 17:24 | AI/Art Renaissance Segment | Optimistic take on creativity in tech era | | 30:13 | Family stories + Uncle Eddie | Touching and funny reflections on growing up | | 47:19 | Birthday/birthday surprise | Joy of ‘Bachelor’ fantasy shopping comes true | | 56:07 | Vintage shopping: from shame to pride | Robby’s personal and societal evolution | | 60:27 | Female friendship/gossip | Closing playful riff on the essential fun of gossip |

Concluding Notes

The episode is an engaging blend of humor, vulnerability, creative insight, and mutual admiration. Robby and Gabby’s chemistry as spouses and creative partners makes for a naturally flowing, candid conversation where laughter and depth go hand in hand. They move from industry talk and Netflix specials to stories of family, love, and overcoming shame, always returning to the theme of authenticity—in art, in relationships, in life.

Don’t miss Robby Hoffman’s Netflix special "Wake Up," out December 14, 2025.

For more: Follow Robby Hoffman (@robbiehoffman) and Gabby Windey (@gabby.windey) on Instagram.