Long Winded with Gabby Windey
Episode: Merry Christmas with Robby Hoffman!!
Date: December 25, 2025
Host: Gabby Windey
Guest: Robby Hoffman
Overview
This festive episode of Long Winded brings Gabby Windey and returning guest/girlfriend Robby Hoffman together for a no-holds-barred conversation: part irreverent holiday hang, part deep dive on American healthcare, sexuality, and the quirks of their relationship. The pair bounce between personal anecdotes, sociopolitical critique, and emotional listener questions — all delivered with Gabby’s signature warmth and Robby’s razor wit.
Main Themes
- Navigating holidays and different backgrounds (Christmas/Hanukkah)
- Scathing, impassioned analysis of the US healthcare system and insurance
- Relationship dynamics: living together, communication styles, and arguments
- Advice on sexuality, queer identity, and relationship anxieties
- Listener call-ins about bisexual awakenings, gender expression, relationship doubts, and more
Key Discussion Points & Insights
1. Holiday Traditions, Interfaith Joy, and Gifting Anxiety
[01:02–05:28]
- Opening banter reflects their mixed religious backgrounds — jokes about “Klausman” and “put on your yarmulke, it’s time for Hanukkah.”
- Both confess to loving Christmas, with Robby joking, “Last year I gave up Hanukkah. Christmas, they just nailed it.” [04:03]
- Anxiety and swapping too many gifts: “Why are we doing this to each other? … if you think you have to get me one more thing and I think I have to get you—maybe we should stop.” — Gabby [02:46]
- Sweet anecdote about Robby’s “pre-gift” on their flight to Cabo, showing how they blend love languages with logistical quirks.
Notable Quote:
“Shout out to the blind community. That’s why podcasts so good. You can be blind and enjoy the podcast.” — Robby [02:13]
2. Life Updates & Jury Duty Snafus
[06:32–07:47]
- Robby receives a jury duty notice in real time, fantasizes about being on the Menendez case, jokes about her suitability for jury service.
- Gabby recalls her own jury experience, using a Bronco’s tryout as an excuse to be dismissed:
“I was like, I’m trying out to be a Denver Broncos cheerleader. This is my plea to be let go. And they let me go.” [08:19]
3. The American Healthcare System, Insurance, and the 'Luigi Mangioni' Case
[08:47–28:01]
- Deep, winding conversation about the failings of the US healthcare system, prompted by “Luigi Mangioni” — a character representing those who take justice into their own hands when insurance denies care.
- Robby launches into a fiery critique of insurance, government, and pharmaceutical “cartels”:
“Insurance companies operating like a cartel with pharmaceutical companies and the government to withhold, deny, depose people's claims. ... This felt more like an anarchist—yeah, you know—like a coup.” [11:21]
- Comparison with other countries:
“We're the only wealthy nation to not... We're the only first world country to offer it.” — Robby [13:38]
- Pointed discussion about how insurance companies are incentivized to deny care and profit from illness:
“When you incorporate profits in that, you're incentivized to keep people sick, to deny their claims, to charge them the most possible amount for health care that they need. It's just, it's immoral and it's not necessary.” — Robby [15:09]
- Gabby and Robby compare the invisible violence of corporate decisions with visible crimes:
“That person has killed so many people because they didn't pull a trigger. That's not how they killed them. They slowly suffocated them. We don't take it as viscerally.” — Robby [26:32]
Notable Exchange:
Gabby: “How does it work? You pay taxes, you get health care. The government subsidizes.”
Robby: “We are not a part of the government. The government has long ago started going—to sit on the phone with customer service… there’s just no way.” [22:42–21:13]
4. Relationship Dynamics, Living Together & Arguing (With Love)
[28:01–38:13]
- Gabby and Robby check in about their relationship—supporting each other's careers, adjusting to living together, and the stress of not having a space that feels mutual.
- Ongoing spat about dishwashers, cleaning, and household tasks provides insight into their communication style and affection beneath the bickering.
“She hates the house. House. She hates it.” — Gabby [34:35] “I don't hate the house... When I don't know the lay of the land ... we keep having a sense that we're moving on the hunt.” — Robby [34:41–37:08]
- They reflect on conflicts, learning “not to take it personally,” and striving to speak up more honestly.
5. Listener Questions: Sexuality, Gender, and Queer Advice
[39:25–76:13]
a. Bisexuality & “Am I Gay?”
[39:32–41:24]
- Caller wonders if her curiosity about women is a sign she's a lesbian.
“Straight girls don't wonder this. ... If you've thought you're bisexual and you've never acted on it, and now you're leaning even more gay—okay, you've had the male counterpart. Now dabble into the woman.” — Robby [39:49–41:11]
- Gabby shares her own experience realizing she was attracted to women.
b. Queer Representation and Gender Expression
[41:25–44:01]
- Another caller thanks them for “super mask/super fem representation” and expresses how rare such couples are in media.
"We're holding up the entire community at this point. I don't know if I'm the right example for this, but thank you for your call." — Robby [43:13]
c. Chest Dysphoria & Top Surgery
[44:18–54:25]
- Caller asks about chest dysphoria during strap-on sex and whether Robby’s surgical decision was influenced by sexual experiences.
“For me, I don't know that it had anything to do particular with me in sexual experiences. ... For me, it's more day in and day out. I just didn't like having a chest.” — Robby [45:48–46:15]
- Robby details her journey, years binding her chest, why she waited, and how top surgery improved her mental health and sense of self.
“As soon as I heard about top surgery, I wanted it. ... I gave myself two years to think about it. ... For me it was way better than I thought it was, like I was. I also had this thing about regret.” — Robby [47:24–51:16]
d. Relationship Security: Dating Non-Cis Men & Insecurities
[55:30–59:38]
- Caller asks how Gabby and Robby handle security in their relationship given Gabby's high-profile dating history.
“If you’re into me, I’m like, so secure because I’m like, there’s something—like, that’s a. I feel like cilantro or something.” — Robby [57:48]
- Gabby describes navigating internalized homophobia and growing comfort, especially after positive experiences as a queer couple.
e. Bisexual Awakening in Hetero Relationships
[61:25–67:47]
- Caller wonders if, after discovering she’s bi while in a relationship with a man, she’ll always have longing.
“You're always giving up something, whether you're giving up the [other gender] to be in a relationship. ... You're giving up other encounters. That's what a committed relationship is.” — Robby [62:56]
- Both acknowledge the temptation of “what ifs”, the value of long-term commitment, and working through feelings in therapy.
f. Travel Compatibility & Wanting More From a Partner
[70:10–74:24]
- Caller loves her boyfriend but worries his lack of worldly experience (and phobia of travel) clashes with her adventurous side.
"You have to decide what's a deal breaker or what's not. ... In any relationship, like Gabby was saying earlier, it's always a compromise." — Robby [71:35] "My thing I'm kind of taking away is: she's afraid to live a boring life." — Gabby [72:25]
g. Relationship Drama & Revenge Hookups
[74:24–76:04]
- Caller seeking revenge on her ex by hooking up with his (revenge) partner’s brother says things are “getting messy.”
“On and off, off again ex—this is nothing. ... If you're single, have fun. ... If he's left you once, it's done.” — Robby [75:13]
Notable Quotes & Memorable Moments
- Healthcare as Violence:
“They're institutionalizing violence. They say it's legal to deny people for services that they purchase.” — Robby [24:33]
- Relationship Check-in:
“I think our biggest obstacle is going to be our careers ... like, staying close.” — Gabby [30:15]
- Long-term, Committed Love:
“I can't wait to see what does 10 years of love look like, what is 15 years? ... It’s the hard-earned drama, but it’s as dramatic in a better way.” — Robby [66:06–69:17]
- Security in Queer Relationships:
“If you’re into me, you’re really just into me, baby.” — Robby [57:48]
- On Being Role Models:
“We're holding up the entire community at this point.” — Robby [43:13]
Timestamps for Important Segments
- [01:02] – Holiday banter, Christmas vs. Hanukkah, relationship dynamics
- [08:47] – Start of deep healthcare discussion
- [16:55] – Comparison to Canadian/European healthcare models
- [26:32] – Institutional vs. direct violence
- [28:01] – Relationship check-in, living together, cleaning disputes
- [39:25] – Listener call: Bi/gay awakening
- [44:18] – Listener call: Chest dysphoria and top surgery
- [55:30] – Listener call: Security in queer relationships
- [61:25] – Listener call: Bisexual awakening in a straight relationship
- [70:10] – Listener call: Partner’s reluctance to travel
- [74:24] – Listener call: Revenge hookups
Tone and Style
- Humorous, irreverent, unapologetic: Gabby and Robbie riff, tease, and digress, but continuously pull meaningful insight from their banter.
- Vulnerable and relatable: Both hosts are candid about their insecurities and admit their flaws.
- Unfiltered social critique: Especially around healthcare, with passionate, pointed delivery.
- Welcoming and supportive: Genuinely affirming to listeners and each other, especially on issues of sexuality and queer identity.
For new listeners, this episode is a perfect microcosm of Long Winded: simultaneously hilarious, fiercely political, and deeply felt — blending holiday antics, complex queerness, real-world woes, and relationship wisdom.