"Robby Hoffman"

A Life in Comedy and Hasidic Roots [0:00]

• Comedian Robbie Hoffman joins the podcast, sharing details about her upbringing.
• Raised in a Hasidic household in Montreal, she is the seventh of ten children.
• Her mother took the children to the library on weekends due to financial constraints.
• Hoffman pursued accounting and began stand-up while in college.

  "She is the seventh of 10 children raised in a Hasidic household in Montreal where money was tight."

Early Career and Mulaney's Endorsement [0:00]

• Hoffman once posed as a courier to deliver a script to HBO Canada.
• She won an Emmy for her writing.
• John Mulaney directed her Netflix special, calling her "one of the funniest people living."

  "He directed her Netflix special, calling her one of the funniest people living, I agree, wholeheartedly."

Identity and Fearlessness [0:00]

• Hoffman describes herself as a "73-year-old man."
• She discusses her perceived fearlessness in comedy, stating she is actually "extremely afraid" all the time.
• This fear, combined with confidence, drives her to address difficult topics.

  "I don't think I'm fearless. I think I'm extremely afraid. Oh, wow. All of the time."

Humor in a Strict Upbringing [0:00]

• Hoffman explains that in her religious community, nothing was off-limits for humor.
• Her family and community were "brutal and funny at the same time."
• There were no concepts of "too soon" or "not the time" for jokes.

  "It's brutal and funny at the same time always."

Family and Childhood Humor [0:00]

• Her mother and father were both funny, but the entire family was known for their humor.
• Childhood involved constant joking, but also physical fights and abuse.
• Laughter and hardship were intertwined.

  "The whole family is funny, but the whole family was also brutal."

The Experience of Wealth [0:00]

• Hoffman shares anecdotes about encountering wealth for the first time, like Sarah Silverman's house.
• She was surprised by the concept of "new towels."
• The idea of luxury items like new towels was foreign to her.

  "I said, new towels? Right. Like, to me, a towel's built with the house."

Social Dynamics of Rich vs. Poor [0:00]

• Hoffman contrasts socializing in wealthy homes with visiting friends' apartments.
• Wealthy homes have strict rules, large islands, and untouched refrigerators.
• Poorer homes are more relaxed, with readily available snacks and a casual atmosphere.

  "And you're just shitting on people. You're sitting there, you're shitting on everyone."

The Ideal Home Setup [0:00]

• Hoffman suggests a compromise: a luxurious mansion with a small, messy kitchen.
• This would combine the dream of wealth with the comfort of a more relatable space.
• The idea is to have a "shit kitchen" behind a beautiful facade.

  "Build out beautiful fucking towels, six sets of towels, sheets, fucking whatever, but the kitchen is a fucking wreck."

Personal Growth and Identity [0:00]

• The conversation touches on Hoffman's experience of growing up Hasidic and questioning her identity.
• She recounts a story about a "camping intensive" gym class in college.
• This experience led to her realizing her attraction to women.

  "And she goes, what if I kissed you? She tells me this. And I'm like, what are you fucking gay?"

Coming Out and Family Reaction [0:00]

• Hoffman discusses her realization of being gay at 17.
• Her father, still religious, sent an email calling her behavior "promiscuous and not befitting."
• Her mother and less religious family members did not take the news well.

  "He wrote me one email, This is not befitting behavior for a daughter of Israel."

Relationship with Gabby Windey [0:00]

• Hoffman is married to Gabby Windey, who was a contestant on "The Bachelorette."
• Windey had 25 boyfriends during her time on the show.
• Hoffman jokes that she "got the final fucking rose."

  "My wife had 25 boyfriends four years ago and I got the final fucking rose in the end."

Meeting Gabby Windey [0:00]

• They met in Los Angeles after Windey's season of "The Bachelorette."
• Hoffman initially mistook a friend of Windey's for someone hitting on her.
• Their initial conversation was filled with excellent banter.

  "And she goes, oh, this Gab, you know, the bachelor. I was like, the bachelor's gay?"

The Bachelorette Experience [0:00]

• Windey described her time on "The Bachelorette" as a paid vacation.
• Contestants had one date per week and traveled extensively.
• As the show progressed, Windey felt pressure and realized her true feelings.

  "She's like, they take you everywhere. You have one shooting day a week."

Vegas Wedding [0:00]

• Hoffman and Windey got married in Las Vegas for $799.
• The package included a limousine, an officiant, and a photographer.
• They opted for a non-religious ceremony.

  "And it included the Reverend, Reverend Nature. Yeah. And it included Nathan, the photographer."

Mulaney's Support for Netflix Special [0:00]

• John Mulaney reached out to Hoffman about creating a Netflix special.
• He had been a fan of her work and offered his support.
• Hoffman described the experience as "shocking, horrifying, and anxiety inducing, surreal, and thrilling."

  "I have been a big fan of your work for a while and really enjoyed you on WTF."

Dream Cars and Father's Legacy [0:00]

• Hoffman discusses her dream car, a Porsche, which connects to her father.
• Her father, despite their estrangement, bought himself a Porsche when their family fell apart.
• Hoffman sees a part of her father in herself through her love for Porsches.

  "And when I'm in the car, I always think of him. This is the car he wants."