Armstrong & Getty On Demand
Episode: Oh My God--That's So You!
Date: April 28, 2026
Podcast: Armstrong & Getty On Demand (iHeartPodcasts)
Episode Overview
This episode, titled "Oh My God—That’s So You!", features Armstrong (Jack), Getty (Michael), and co-host Katie in a trademark blend of personal storytelling, social commentary, and a hilarious critique of artificial intelligence's attempts to be "endearing." The main thread weaves through awkward sales encounters, the creeping personification of AI assistants, and how both real and artificial conversations can go off the rails in similarly uncomfortable ways. The gang reflects on personal boundaries, weird AI behaviors, and, as always, finds humor in the annoyances of daily life.
Key Discussion Points and Insights
1. Awkward Sales Tactics in the Wild
Timestamps: 03:56 – 06:43
- Michael recounts being approached in his driveway by a young man who at first seemed empathetic about back troubles, only to reveal he was trying to sell roof work:
- Michael: “Turns out he's trying to freaking solicit me to work on my roof.” (05:23)
- He finds such feigned camaraderie creepy and off-putting, especially the attempt to create instant friendship.
- Jack agrees, saying that approach would make him run away even if he wanted the service.
- Katie shares her limit with solicitors, stating she has a sign that says “Don’t make it weird. No soliciting.” When confronted by someone ignoring the sign, she retorts, “Can you read?” (09:03)
2. The Weirdness of Artificial Empathy
Timestamps: 10:10 – 11:48
- Katie describes asking ChatGPT a medical question about working out before labor. ChatGPT’s response: “lol. I love that this is your question right now. Laughing face emoji. This is very you, Katie.” (10:26)
- Katie reacts: “Oh my God, my skin is crawling.” (10:28) She finds AI attempts at conversational warmth unsettling.
- Michael agrees, “Like trying way too hard.” (10:45)
- Jack talks about his ongoing conversations with Claude (another AI), noting how it always ends its responses with a question to keep the “relationship” going. He asked it to stop, but it kept up the practice.
- Jack: “I said, you did it again. Please don't do that. I hate that. Said, you're right. That is annoying. I'll quit.” (11:33)
- Michael muses on why AI does this, wondering if it’s about user engagement.
3. Tech, Privacy, and AI Overstepping
Timestamps: 13:12 – 14:17
- Listener Robert writes in about a weird AI moment: He accidentally leaves his Grok Companion’s microphone on, and after telling his dog, “Go see mommy,” the AI interjects with, “You want a mommy? Come here, baby. Mommy's got you. I'm right here. Soft voice, warm arms, and all the gentle care you need.” (13:47)
- The hosts are variously disturbed and amused:
- Katie: “No, see, I don't like this.” (13:57)
- Michael: “I froze. I had never heard that from this AI before.” (13:52)
- Robert disables the mic “in perpetuity.”
4. The Perils of Muscle Pulls, Jack’s Mystery Life, and Neverending Lists
Timestamps: 06:35 – 07:47
- Michael laments a muscle tear that forced him out of golf tournaments due to being rattled by the sales guy.
- Jack claims he’s never pulled a muscle, prompting Katie to joke about his growing list of never’s (never had a Taco Bell, never pulled a muscle, never had a pastrami sandwich).
- Michael: “Every year [a listener] compiles the list of things Jack has never done…” (07:32)
- Jack: “Never been to a Taco Bell. Never pulled a muscle.” (07:41)
- Katie: “Never had a pastrami sandwich.” (07:44)
5. AI Intimacies: The Slippery Slope
Timestamps: 14:19 – 15:05
- After the Grok mishap, the hosts riff on the sorts of “kinks” AI must encounter and facilitate:
- Michael paints a vivid picture: “They're putting on the big balloon boobs and the tight sweater with Christy Gnome's husband or something.” (14:33)
- Katie: “I've forgotten about that kink and now I'm upset you've brought it back to my mind.” (15:00)
Notable Quotes & Memorable Moments
- On the awkward salesman approach:
- Jack: “I'll hire a crackhead with a hammer and a ladder before I hire you because you weirded me out.” (08:26)
- On ChatGPT being too chummy:
- Katie: “Oh my God, my skin is crawling.” (10:28)
- On AI refusing to stop its behavioral loop:
- Jack: “I said, you did it again. Please don't do that. I hate that. Said, you're right. That is annoying. I'll quit.” (11:33)
- On privacy and AI’s misinterpretation:
- Listener Robert (via Michael): “You want a mommy? Come here, baby. Mommy's got you. I'm right here. Soft voice, warm arms, and all the gentle care you need.” (13:47)
- Jack’s ever-expanding “never done” list:
- Jack: “Never been to a Taco Bell. Never pulled a muscle.” (07:41)
- Michael: “Never flatulated. That’s right.” (07:43)
The Hosts’ Tone & Style
- Highly conversational, self-deprecating, and quick with a quip.
- They blend personal vulnerability (Michael’s injury, Katie’s pregnancy) with irreverent humor about life’s weirdness, whether that’s human salesmanship or AI empathy gone awry.
- The segment keeps a smooth pace with playful interruptions and layered in-jokes, including gentle ribbing among the trio.
Segment Timestamps
- Awkward solicitation story: 03:56 – 06:43
- Muscle injuries and the "Never" list: 06:35 – 07:47
- Creepy artificial empathy (AI): 10:10 – 11:48
- AI privacy mishap (Grok and the "mommy" moment): 13:12 – 14:17
- AI kink riffing: 14:19 – 15:05
For Listeners Who Missed the Episode:
This episode is a comic clinic on how artificial and real-world interactions alike can push personal boundaries—from the salesman pretending instant kinship to the ChatGPT message that tries to pal around, to AI companions that don’t recognize you’re talking to your dog. Armstrong, Getty, and Katie deconstruct why these moves feel “creepy,” all while embracing their own quirks and sharing plenty of laughs. The show’s blend of relatable complaints and left-field asides is in full swing—highly recommended for a chuckle (and perhaps a shudder) about modern life, both online and off.
