The Bert Show: "Vault: Wendy's Creepy Craigslist Adventure"

Air Date: March 18, 2026
Main Cast: Bert, Wendy, Chris, Jeff, Mary, Callers & Listeners

Episode Overview

In this episode, The Bert Show team dives headfirst into the wild, weird world of Craigslist personal ads. The main theme centers on testing the "creepiness" of Craigslist by having Wendy post an ad in the "encounters" section and see how quickly it elicits a response. The hosts and listeners share stories, reactions, and even craft a Craigslist-inspired haiku, all while keeping things light, humorous, and a little risqué. The episode explores internet anonymity, personal boundaries, and online dating mishaps, all in the classic, irreverent Bert Show style.

Key Discussion Points and Insights

1. Kicking Off the Craigslist Experiment

• (00:45) Bert sets the stage: Wendy has just posted a provocative ad in the Craigslist encounters section. The gang is waiting to see how long it will take to get a reply.
• Wendy’s ad:
  “I'm open to trying new things and I love dirty talk, so turn me on. Fetishes Freaky? Yes, please. I'm not picky on appearance. We'll leave work immediately. Please call phone number. Need some asap.”
• They joke about the sheer volume of competition on Craigslist and the speed with which new ads appear, pushing Wendy’s post further down the list.

2. Listener Stories about Craigslist Weirdness

• (01:44) Mary’s story: She shares about receiving a mistaken call from a hotel room in Fayetteville, from a man responding to a Craigslist ad for “Lindsay.” This sparks a discussion about prank posts and the downsides of someone else's mistaken or malicious postings.
• Mary: "I have no idea. I don't know if you dialed the wrong number or somebody put the wrong number. But, like, a couple of people have called me since then thinking that I am this Lindsay person, wanting to hook up with them in a hotel." (03:06)

3. Browsing The Craigslist Encounter Section

• (03:36) Bert’s first time in the Craigslist encounter section: He's shocked and amused, reading aloud actual posts, highlighting the explicit and sometimes bizarre nature of the ads.
• Sample Postings Read by Bert:
  • "Special feet lovin’"
  • "Looking to have fun with a vanilla kitty?"
  • "Any bored housewives looking for daytime encounter?"
  • "Hump day humping."
    ("Seriously? That was their pitch line?" – Listener 1, 04:53)
• The group jokes about how clever or desperate some of the ads are and the colorful language used.

4. Craigslist Pranks and Online Dangers

• (06:11) Listener Call: A male listener admits to once pranking his married friend by posting a "men seeking men" ad with his real phone number, specifying odd roleplay requests. This spins into a playful yet cautionary chat about the risks of these types of pranks.
• Chris: "That's actually funny... say, look, I'm way into role playing, so no matter what, you are my middle school scout leader." (06:29)
• They touch lightly on the fleeting nature of posts—so many go up every few seconds that any embarrassment is short-lived.

5. Success Stories and “Casual Encounter” Nuance

• (07:21) Another caller shares a positive Craigslist story: She met her boyfriend via a Craigslist ad in "men seeking women," distinguishing it from the more salacious "casual encounter" section.
• Caller: "It's actually crazy because I did my own research, and the females are just as nasty." (07:43)
• She emphasizes the different intentions behind the sections—some looking for flings, others looking for genuine connections.

6. Craigslist Haiku Challenge

• (09:15) Chris writes a Craigslist-inspired haiku:
  • "Where should I
    Slap you like autumn leaves
    your pants fall. I don't know your name." (10:02)
• The team debates the correct haiku form and playfully applauds (snapping fingers) for Chris’ poetic effort.

7. The Results: Waiting for Wendy’s Response

• (10:16) Ten, twelve, then thirteen minutes pass with no reply to Wendy’s ad, surprising everyone given Craigslist’s reputation.
• The group speculates about why no one’s calling (maybe Wendy’s ad got lost in the shuffle, maybe Atlanta Craigslist isn’t as fast-moving as rumored).
• Bert: "Maybe Craigslist isn't as creepy as you guys thought it was." (10:19)

8. The Creepy Call Arrives

• (10:40) Wendy finally gets a call: She answers live with encouragement from the crew, but the caller quickly hangs up after a brief, awkward interaction.
  • Wendy: “He’s like, I’m responding to your ad. And then just sat there silently. And then I’m like, where are you? He was like, I’m in my car.” (11:04)

Notable Quotes & Memorable Moments

• Wendy: "Nobody really wants to do me on Craigslist yet." (00:51)
• Listener 1: "People post the most disgusting things on that, like, pictures and everything." (03:00)
• Bert: “Looking to have fun with a vanilla kitty? What is that?” (04:25)
• Listener 1: "That was their pitch line? Hump day humping." (04:53)
• Chris's Haiku:
  • "Where should I / Slap you like autumn leaves / your pants fall. I don't know your name." (10:02)
• Wendy (on the call): “He’s like, I’m responding to your ad. And then just sat there silently. And then I’m like, where are you? He was like, I’m in my car.” (11:04)
• Bert: "Maybe Craigslist isn't as creepy as you guys thought it was." (10:19)

Timestamps for Key Segments

• Craigslist Ad Goes Live: 00:45
• Mary's Wrong-Number Story: 01:44–03:06
• Bert Reads Craigslist Ads: 03:36–04:57
• Craigslist Prank Call Story: 06:11–06:48
• Caller Shares Craigslist Relationship: 07:21–08:38
• Haiku Challenge & Readings: 09:15–10:13
• First (and Only) Call to Wendy's Ad: 10:40–11:04

Tone and Style

The episode is light, irreverent, and at times, gleefully naughty. The crew’s reactions are quick, humorous, and authentic, balancing curiosity and caution as they explore Craigslist’s wilder side. Listeners join in with their own candid—sometimes cautionary, sometimes heartwarming—stories.

For Listeners Who Missed the Episode

• Expect lots of laughter, a bit of shock, and the kind of honest, anything-goes conversation The Bert Show is known for.
• This episode peeks behind the digital curtain at Craigslist’s personal ads, showing both the absurdity and the occasional sweetness of strangers reaching out online.
• It’s a playful warning about online anonymity and a testament to the bizarre, unpredictable world of Internet connections—plus, don’t miss Chris’s legendary Craigslist haiku!

Note: Ads, intros, and outros are omitted in this summary.