The Bert Show – “Vault: Did This Wedding Crasher Succeed?”

Release Date: January 15, 2026
Podcast Host: Pionaire Podcasting
Episode Theme:
This episode dives into a real-life “wedding crasher” mission. The Bert Show crew reconnects with a listener named Charlie who set out to “crash” a wedding in Tennessee over the weekend. The hosts check in after his adventure to find out if Charlie’s bold attempt to hook up with someone at an out-of-town wedding—where he was not exactly a close invite—actually succeeded, what tactics he used, and get the inside scoop on guest drama and hijinks. With their trademark banter, the team dissects Charlie’s story, pokes fun at his bravado, and adds layers of playful skepticism.

Key Segments & Discussion Points

1. Setup: Charlie’s Wedding Crashing Plan

[01:18–02:46]

• The hosts revisit a call with Charlie, who’s excited to “crash” a wedding and, in his words, “do well” with the guests.
• Charlie believes, “The worse the groom, the better chance I have.” ([01:26], Charlie)
• He plans to present himself as a nice, maybe “a little shy” guy, leveraging being slightly older and more successful than most of the young guests.
• The show teases skepticism about Charlie’s confidence but sets up a Monday morning check-in to see how his plan unfolds.

2. Monday Recap: Did Charlie Get Lucky?

[02:49–07:42]

• Back on the voice disguiser, Charlie describes arriving at the wedding and ultimately getting together with the bride’s sister, who was the maid of honor.
  • “But I did get laid.” ([03:42], Charlie)
  • He jokes that if he’d said he didn’t, the hosts would believe him, but as he claims success, they remain skeptical.
• Tactics Explained:
  • Charlie notes he couldn’t concoct too many stories about himself as his own sister was at the wedding.
  • The actual “in” was to bond with the maid of honor over humorous gripes about the other maid of honor, rather than poking fun at the bride or groom.
  • “The tactic that we used like that was making fun of the other maid of honor, but not the bride, of course.” ([06:07], Charlie)
• Wedding Night Details:
  • Charlie admits to a night of drinking and flirting that ended “by 4:30 in the morning” in the maid of honor’s family suite.
  • “It was already like 4:30 in the morning, so it had to be quick, you know.” ([07:21], Charlie)
  • The hosts jokingly grill him on whether alcohol was involved and poke fun at his “gentlemanly” conduct.
  • “I don’t take advantage of anyone who’s passed out. But if they’re drunk, it’s all right.” ([06:31], Charlie)
  • Show’s Tone: The Bert Show crew responds with characteristic sarcasm and humor, feigning admiration while calling out Charlie’s dubious standards.
  • “A guy with a heart, no wonder why they fall for you.” ([06:48], Burt Show Host 2)
• Charlie's Retrospective:
  • He claims, tongue-in-cheek, that he “just did it for you guys”—referring to the show and its listeners.
  • “Change my ways. But I thought I had to prove something.” ([07:34], Charlie)
• The hosts close the segment by playfully questioning Charlie’s truthfulness but thank him for the entertaining update.

Notable Quotes & Memorable Moments

• Charlie on wedding “strategy”:
  • “The worse the groom, the better chance I have…” ([01:26], Charlie)
• On being a good catch:
  • “I’m sort of a good catch, you know…but maybe I’ll just be like a little self-effacing.” ([02:15], Charlie)
• On his confidence:
  • “It’s a sure thing, man.” ([02:46], Charlie)
• On his ‘success’:
  • “But I did get laid.” ([03:42], Charlie)
• Regarding being a ‘gentleman’:
  • “I don’t take advantage of anyone who’s passed out. But if they’re drunk, it’s all right.” ([06:31], Charlie)
  • “When she’s unconscious and you don’t do her—oh, man.” ([06:44], Burt Show Host 3, sarcastic tone)
• Hosts questioning veracity:
  • “…we’re not sure if you’re telling the truth or not, but we just gotta go with what we hear.” ([07:36], Burt Show Host 2)

Key Timestamps

• [01:18–02:46]: Charlie’s wedding crashing plan and expectations
• [03:09–04:20]: Charlie’s persona at the wedding and the mechanics of his flirtation
• [05:24–06:13]: The mechanics of “picking up” the maid of honor and establishing rapport
• [06:17–07:26]: Drinking at the wedding, ending up together, and post-party antics
• [07:31–07:42]: Charlie’s humorous justification for his actions and the hosts’ wrap-up

Overall Tone & Takeaways

• The episode features Bert Show’s hallmark mix of real talk, ribbing among hosts, bold listener stories, and a touch of voyeuristic drama.
• The conversation is irreverent and cheeky, at times pushing boundaries of taste but always self-aware.
• The hosts keep the mood light even as they scrutinize Charlie’s claims, poking fun at both him and wedding culture.
• The story highlights the comic absurdity and social dynamics of weddings, the phenomenon of “wedding crashing,” and the role of alcohol, group dynamics, and lighthearted scheming in such events.

For Listeners:
If you enjoy stories of social daring and wedding shenanigans, or are just into fun, unfiltered morning radio dynamics, this episode is a lively and irreverent look at what goes down behind the scenes at someone else’s special day. Expect laughs, skepticism, and plenty of side-eye for Charlie’s “gentlemanly” exploits.