The Bert Show – ‘Vault: Bert Solves Wendy’s Dating Desperation’ (March 25, 2026)

Episode Overview

This lively Bert Show classic centers on helping Wendy overcome her persistent dating struggles, which the team lovingly dubs “dating desperation.” Hosts Bert, Kristin, and additional cast members offer Wendy blunt but supportive advice: how to let go of desperation, stop trying too hard, and allow romance to unfold naturally. They invent a unique experiment—Bert will take over Wendy’s dating messages for a weekend, to demonstrate “the game” and reclaim her dating mojo.

Key Discussion Points & Insights

1. Wendy’s Dating “Desperation” and its Perception

• The hosts confront Wendy about projecting desperation when single, with Bert stating plainly that “guys can smell it.”
  • Bert: “I’m not trying to come down hard on you, but the truth of the matter is… you come from a place of desperation, and guys can. We can smell it.” (00:56)
• Kristin (and others) clarify their critique is meant to empower Wendy, reminding her she has plenty to offer and doesn’t “need” to try so hard.

2. Specific Behaviors That Signal Trying Too Hard

• The group recalls an incident where Wendy dressed up far too formally for a casual lake outing—an example of trying to impress too much.
  • [A]: “Everybody’s in the driveway with flip flops... and you come down in a black dress, full makeup, and heels. Like, that is a desperate move right there.” (02:02)

3. The Dating “Game”—Is it Necessary?

• The hosts debate the need for game-playing in modern dating.
  • Wendy resists the idea, wanting to be honest and authentic:
    • C: “Games are stupid. Someone’s gonna like you whether you play a game or not, right?” (03:59)
  • Bert and the others push back, insisting that withholding some interest or access increases attraction:
    • B: “In the dating world, that doesn’t work. You gotta play the game.” (03:47)
  • The “Rules” book is discussed, illustrating old-fashioned “don’t call back right away” strategies. The group admits results vary, but maintains boundaries are key.

4. Demonstrated Experiments: Bert Takes Over Wendy’s Dating

• The on-air team recounts a prior instance of Bert managing a man’s romantic communications with success—until the man reverted to old, too-eager habits, and the relationship fizzled.
  • [A]: “…it worked perfectly—95% of the time. …It all fell to pieces when…he took matters into his own hands, and he lost the girl in, like, 24 hours.” (06:19–06:43)
• A new experiment is proposed: Bert will handle all text exchanges with men Wendy meets, using a secondary phone. The plan is to:
  • “reel in” prospects by controlling the pace,
  • show Wendy, via example, how to avoid over-eagerness and preserve intrigue.
  • B: “I am going to be you texting all weekend long, and I’m going to show you how this is done.” (07:48)

5. Listener Wisdom: Let Men “Hunt”

• Brandy, a caller, chimes in to agree that “the chase” is still essential for men.
  • C (Jen): “Men are hunters. Let them hunt.” (09:45)
• The group extends the analogy, humorously likening Wendy’s approach to being a deer that jumps willingly into the hunter’s truck—thus spoiling the challenge.
  • C: “You jump into their truck and you say, here I am. You’re a deer that jumps into the back of the truck…” (09:49)
  • A: “They have the rope in their mouth and, like, tie me to the hood.” (10:02)

6. Encouragement and Final Notes

• The segment wraps with both good-natured teasing and genuine encouragement, reinforcing that Wendy deserves someone who will make an effort for her.
  • A: “You deserve a guy that’s willing to climb in the tree and cover himself in urine…that’s what you deserve.”
  • B: “Just let me get them on the boat. …You can make them a trophy, you can eat them, whatever. But I’m going to bring them in.” (09:08)

Notable Quotes & Memorable Moments

• On Desperation:
  • Bert: "You come from a place of desperation and guys know it. Am I wrong here?" (01:59)
  • [A]: “That is a desperate move right there.” (02:02)
• On Playing the Game:
  • Bert: “You have to act. That’s…the game we’re trying to tell you.” (03:47)
  • Kristin: “Games are stupid. Someone’s gonna like you whether you play a game or not, right?” (03:59)
• Analogy – The Deer in the Truck:
  • Jen: "Men are hunters. Let them hunt." (09:45)
  • Kristin: "You're a deer that jumps into the back of the truck and goes, just says, here, I'm already here. I'm already dead." (09:57)
• Experiment Plan:
  • Bert: “When you meet guys this weekend, you give them this phone number, okay? They’re gonna think they’re texting you, but they’re really texting me. And I’m gonna play it all weekend long.” (07:20)

Timestamps for Major Segments

• 00:47 — Show begins, addressing Wendy’s single status and “zero mojo”
• 02:02 — Example of ‘trying too hard’: Dress at the lake outing
• 03:47–04:04 — Debate about whether “the game” is necessary in dating
• 06:19–06:48 — Recap of prior experiment: Bert coaches a man in dating
• 07:20–09:14 — Announcement and setup of the new “Wendy’s Dating” experiment
• 09:29–10:52 — Hunting analogy & listener calls encourage letting men “chase”
• 11:10+ — Segment wraps with teasing and plans for experimenting

Tone & Takeaways

The episode is frank, comedic, and supportive. While the team pokes fun at Wendy’s “desperation,” their intent is to empower her to be more confident and strategic. The “dating game” is dissected with both skepticism and real-world support. Memorable analogies and innovative radio experiments keep it engaging and relatable throughout.

Key Takeaway:
To find genuine connection, stop projecting neediness and let potential partners come to you—sometimes, a little game playing helps maintain your own value and intrigue. And if you can’t do it yourself, maybe let Bert run your love life (at least for a weekend).