Bad Friends – "Rudy Loves Chocolate" (October 27, 2025)

Episode Overview

In their signature blend of wild, irreverent, and brutally honest banter, Andrew Santino and Bobby Lee host a raucous Halloween episode with regulars Isa (“Rudy”), Carlos, and guest Dax Flame. The gang dives into recent adventures, romantic escapades, dominatrix culture, dating dilemmas, a hilarious game of Halloween trivia, and plenty of self-deprecating, pointed observations. This episode leans into themes of experimentation in life and love, group dynamics, money etiquette, and the primal realities of human connection—with all the sharp, silly, and chaotic energy fans love.

Key Discussion Points & Highlights

1. Birthday Party Stories & Halloween Vibes (00:33–03:00)

• Reminiscing about an epic birthday party featuring Chef Yoon, a sake Super Soaker, and wild grill stunts.
  • Andrew: "Show the Saki squirt gun...there's Max getting right in the mouth."
  • Carlos: "He hits himself in the face. Not once...He does it twice." (01:30)
• Giddy, Halloween-centric energy as they launch into a messy, improvised jam celebrating the spooky season.

2. Rudy's Dating Life & 'Chocolate' Preference (03:19–04:07)

• The group teases Isa about her new romantic flings, emphasizing her current preference for "chocolate" (dating Black men).
  • Andrew: "Sleeping over at black guy's houses...Walking out bow-legged, Jewels. What have you been doing?" (03:29)
  • Isa: "Just seeing a couple of people."
  • Carlos: "[To Isa] Every time...it's this gigantic, handsome Black guy. Every time." (03:46)
  • Andrew: "You like a little bit of chocolate now, huh?...You love chocolate." (03:52)

3. Trying New Things & Furry Costumes (04:07–05:54)

• Debate over dating diversity, Carlos’s desire to try a furry costume, and the comedic fascination with the furry community.
  • Carlos: “I’ve always wanted to try [a furry suit] since I saw it on Entourage.” (04:29)
  • Andrew: "Shout out to the furry community..."
• Andrew discusses meeting dominatrices in Vegas:
  • "I was like, how many guys get like genital mutilation? She’s like, a ton. A high amount of people." (08:13)

4. Dominatrix & Sexual Experimentation (07:55–10:55)

• Hilarious, graphic descriptions of dom/sub fantasies and pain thresholds.
  • Andrew: "I'm missionary for a minute and a half and then go to bed." (08:49)
  • Carlos: “Level two is what? Two cheeks?...Maybe stick a toothpick inside the penis hole.” (09:40)
  • Andrew: "That's level five or six. You're skipping!" (09:46)
• Honest discussion about the psychology and economics of kink culture.

5. The Porn Industry & the Role of 'The Cuck' (10:57–12:01)

• Andrew recounts meeting a small Filipino porn actor who specializes in cuckold roles.
  • Andrew: "He started off as a shooter...Now...I'm the cuck...I just have to watch." (11:21)

6. The 'Hot Wife' / Cucking Discourse (12:05–13:18)

• The white-hot, comedic explanation of "hot wives" and the hierarchies within non-monogamy.
  • Andrew: "Consensual, non-monogamy."
  • Carlos: "I want to be with that ugly wife...I'll be the hot husband." (12:48)

7. Dating Out of Your League (13:02–13:47)

• Andrew ribbing Carlos on the punchline that men routinely “date out of their league.”
  • Andrew: "Every guy we know dates women out of their league." (13:22)

8. Adventures in Vegas and Gambling Woes (13:52–15:18)

• Andrew details a packed Vegas weekend: emo festivals, gambling losses, intergenerational hijinks with Shane Gillis and his dad.
  • Andrew: "Shane on fire...He was winning...I lost all my money." (14:50)

9. Entourage Dynamics, Comedy Touring & Paying for the Crew (15:22–20:02)

• Carlos complains (humorously) about footing huge dinner bills for his entourage while on tour.
  • Carlos: “I have a lot of entourage now. But my problem is...No one has money.” (15:56)
  • Andrew: “There is a code of standup. You are supposed to pay for your openers.” (18:54)
• The etiquette and burdens of travel, hospitality, and comedy hierarchies (“the hierarchy pays”).

10. Who Pays on Dates? Gen Z Perspective (24:50–25:06)

• Isa never pays when dating, nor offers to split the check.
  • Isa: “Oh, I don’t pay.” (24:55)
  • Andrew: “You cannot pay. Do you offer half? You don’t even do that.” (24:57)
  • Isa: “No.” (25:00)

11. Dating Women with Kids (25:09–27:35)

• Playful debate on single parent dating, bringing kids to dates, and tolerances for age of the child.
  • Andrew: “5, 5, 6. Kinda the cutoff. If she brings a 10 year old—that's bananas.” (25:34)
• Carlos’s misadventures with a girlfriend’s pre-teen son (26:50).

12. Serial Killers, Childhood Trauma, & Pop Culture (30:03–38:41)

• The crew riffs on the making of serial killers, bedwetting, and their prevalence in American vs. international culture.
  • Carlos: “Highest concentration of serial killers has got to be from here.” (37:37)
  • Andrew: “We’re number one again!” (37:41)
• Short tangent on the BTK Killer and how “the drawing looks like Bobby.”

13. Halloween Trivia Showdown (54:24–63:27)

• Dax Flame acts as quizmaster for Halloween and horror movie trivia, leading to chaos, trash talk, and surprise upsets.
  • Dax: "Which famed horror actor performed the monologue in Michael Jackson's Thriller?"
    Bobby: "Vincent Price." (59:30)
  • Running joke about Carlos always losing and Dax’s “negative energy.”

14. Candy Preferences, Snickers Jokes & Going Solo (64:00–67:30)

• Goofy, slightly risqué riffing on Halloween candies.
  • Andrew: “The Reese’s Peanut Butter Cups are shaped like pumpkins—my favorites.” (64:29)
  • Carlos: "I went roller skating again last night by myself...The most lonesome human experience you could ever have." (65:30, 66:20)
• Meditations on independence, dying alone, and the bittersweetness of solo life.

15. First Kiss Advice & Dating Anxieties (68:00–74:59)

• Bobby and the gang dissect how to initiate a first kiss—directly asking vs. waiting for signals.
  • Bobby: "It's really hard. First kiss is such a hard thing to know how to do. You ever ask?" (68:58)
  • Bobby: "Should we kiss or something?" (70:14)
• Final segment on performative masculinity, intimacy, and goofy “bear” metaphors for kissing.

Notable Quotes

• Andrew Santino:

  • "You like a little bit of chocolate now, huh? You love chocolate." (03:52)
  • "Consensual, non-monogamy." (12:48)
  • “There is a code of standup. You are supposed to pay for your openers.” (18:54)
  • "Every guy we know dates women out of their league." (13:22)

• Carlos:

  • “Maybe stick a toothpick inside the penis hole.” (09:40)
  • "I have a lot of entourage now...my problem is...no one has money." (15:56)

• Isa ("Rudy"):

  • "I love chocolate." (03:54)
  • "Oh, I don't pay." (24:55)

• Bobby Lee:

  • “It’s stupid to talk about this crap. Let’s talk about something smarter.” (53:43)
  • "First kiss is such a hard thing to know how to do. You ever ask?" (68:58)
  • "Should we kiss or something?" (70:14)
  • “I love you.” (71:36)

Segment Timestamps

• [00:33]–[03:00]: Chef Yoon & Halloween jam
• [03:19]–[04:07]: Rudy’s dating preferences, “chocolate” jokes
• [04:07]–[06:09]: Fur-suits, Dominatrices, Vegas hijinks
• [08:13]: "Genital mutilation" kink culture
• [10:57]–[12:01]: Cuckold roles in porn
• [12:05]–[13:18]: “Hot wife,” hierarchy of non-monogamy
• [13:02]–[13:47]: Dating out of your league
• [13:52]–[15:18]: Vegas trip recap
• [15:22]–[20:02]: Entourage, comedy touring, paying etiquette
• [24:50]–[25:06]: Who pays on dates
• [25:09]–[27:35]: Dating with kids, cut-offs for tolerance
• [30:03]–[38:41]: Serial killers, trauma, pop culture
• [54:24]–[63:27]: Halloween trivia game
• [64:00]–[67:30]: Candy favorites, Snickers joke, solo skating
• [68:00]–[74:59]: First kiss advice, performative masculinity

Memorable Moments

• Andrew and Isa’s “chocolate” jokes become a running callback throughout the episode, setting a bawdy, playful tone.
• Carlos’s escalation from “light smack” to “toothpick in the penis” when discussing BDSM levels—a highlight of the group’s outrageous humor. (09:20–09:46)
• Group trivia turns into an absurd battle with frequent accusations of unfairness (and Bobby’s surprise win on a Beetlejuice question!).
• Carlos's solo roller-skating saga told as both comedy and existential crisis.
• End-of-episode play-by-play on how to master a first kiss, culminating in a ridiculous “bear and honeycomb” metaphor.

Tone & Style

The episode is fast-paced, raunchy, and deeply self-aware. The hosts’ chemistry comes through in relentless teasing, ego clashes, and an undercurrent of genuine affection. Jokes are dark, playful, and occasionally provoke the boundary between earnest vulnerability and raw, punchline-driven chaos.

For listeners new and old, ‘Rudy Loves Chocolate’ is classic Bad Friends: fearless, filthy, and deeply human beneath the madness.