The Bert Show – Vault: One Of The Worst Dates Ever!

Podcast: The Bert Show
Date: November 10, 2025
Hosts: Bert, Kristin, Abby, Cassie, Tommy & The Bert Show Cast
Episode Theme:
A hilariously cringeworthy exploration of one of the most awkward and disastrous first dates ever—and the jaw-dropping aftermath—centered on a viral real-life story. The cast walks listeners through a saga of escalating emails, voicemails, and even a restaurant call, all set off by a $50 dispute after a one-off dinner.

Main Theme / Purpose

This episode dives into the infamous real-life story of Darren Sherman and Joanne—a date gone spectacularly wrong, featuring relentless requests for a $50 repayment after a single dinner. The hosts relive each outrageous step, read direct voicemails and emails, and offer pointed, often hilarious commentary on modern dating etiquette, entitlement, and when persistence simply becomes stalking.

Key Discussion Points & Insights

1. The Setup (01:02–02:45)

• Background:
  Darren Sherman, CEO of a New York financial firm, meets Joanne on JDate ("It's basically match.com for Jewish people," explains Bert. [01:26])
• Venue:
  Their date is at China Grill, a "really nice, fancy" spot in NYC.
• Split or Not?:
  Joanne offers to split the bill. Darren declines, offering to cover it all.

  "Nah, nah, nah, don't worry about it, I'll pick it up." — Bert [02:56]

2. The Fallout (03:00–04:22)

• Change of Heart:
  Darren senses there's no spark/no second date. He sends Joanne an email:

  "Sorry things didn't work out... Here is my address for the 50 bucks." — Bert paraphrasing Darren’s email [03:35]

• Hosts' Reaction:
  The cast is incredulous at the immediate pivot from chivalry to a request for reimbursement.

3. The Voicemails Begin (04:22–07:23)

• Aggressive Follow-up:
  After no reply, Darren leaves a pointed voicemail, threatening “to keep on top of this” and even mentioning “issuing you a summons” if she doesn’t pay up.

  "Be a mensch... Just get it done, drop it in the mail... I don't think you want me to keep on top of this. It's your call. Don't be cheap here."
  — Darren's voicemail [04:47–06:17]

• Hosts analyze:
  They break down Darren’s repeated refrains and assumptions, especially his belief he was owed another date (and reimbursement) because he paid.

4. Escalation & Email Ping-Pong (07:23–09:38)

• Continued Pressure:
  Darren follows with more emails, requesting Joanne to acknowledge she'll repay.

• Joanne’s Boundaries:
  She finally replies:

  "I had every intention of calling you... but your email has completely turned me off and I find it extremely tacky. I will not be sending you any money since I offered that night to pay and you told me no that you would take care of it." — Joanne [08:19]

• Darren’s Response:
  He pastes his American Express bill in an email, writing:

  "Do the right thing, Joanne." [09:06]

• Hosts’ Banter:
  Speculation about Darren’s “10% tipper” vibes and how he’s “absorbing two thirds of the meal” for her [09:09–09:38].

5. Threats Become Legal and Workplace Oriented (09:38–13:46)

• Threats Escalate:
  Darren leaves voicemails threatening to contact Joanne’s employer or “issue a summons at your job for just $15.”

• Joanne Stands Firm:
  She responds calmly but firmly:

  "You may want to rethink the tacky approach about asking someone for money... I will also let your clients and employees know about your erratic and bizarre behavior."
  — Joanne [11:06]

• More Voicemails:
  Darren, undeterred, doubles down:

  "You ate the food, you drank the wine. Finally pay your dinner. Just business at this point." — Darren [13:46]

6. Office Watercooler & China Grill Finale (14:00–17:22)

• Hosts Imagine:
  Cassie, Kristin, and Bert joke about Joanne’s office gathered around to listen to the ever-escalating voicemails.

  “Oh my God, do you think that every time she gets this voicemail, she gets all of her... office, ‘Oh my God, he called again!’” — Kristin [13:49]

• Darren Calls the Restaurant: He contacts China Grill, trying to get them to intervene and collect Joanne’s $50 share.

  "I'm looking to settle this nicely, but... do the right thing." — Darren, one more time [16:13]

• China Grill’s Voicemail:
  The manager calls Joanne to "split the bill" [16:47].

• Resolution:
  Joanne explains the entire ordeal to China Grill, who comp her meal and offer free drinks [17:03].

  "China Grill... completely comp it for her. And they even give her free drinks the next time she's in. So that's how the whole thing ends." — Bert [17:20]

7. Reflection and Final Thoughts (17:22–19:29)

• Hosts’ Outrage & Amusement: The group ponders how Darren could possibly believe he’s right.

  "Do you think his friends are like, right on, man... Because you surround yourself with people that are like you." — Bert [17:43]

• Notable Listener Call:
  Linda calls in:

  "This guy's a stereotype, but... he is a class jerk. There isn't a judge on earth that would listen to half of that plea." — Linda, caller [18:17]

• Takeaways:
  The story spreads online, leaving Darren “with a scarlet letter,” and the hosts hope none of their listeners ever encounter such a disastrous date.

Notable Quotes & Memorable Moments

• "Be a mensch... Just get it done, drop it in the mail... Don't be cheap here."
  — Darren's first voicemail [04:47–06:17]

• "I had every intention of calling you... but your email has completely turned me off and I find it extremely tacky."
  — Joanne’s first response [08:19]

• "You ate the food, you drank the wine, you didn't call back in two and a half weeks."
  — Darren, repeatedly [throughout his voicemails]

• "He wants his $50. So she listens to that very voicemail... and again, she doesn't respond back to him."
  — Bert, exasperated [07:26]

• "I'm going to call the employer and garnish the wages. Okay."
  — Bert, reacting to Darren's message [10:34]

• "After your voicemails, you've now entered the world of a first-class creep. Dating is not business. I offered to go Dutch at the time... you declined. As far as I'm concerned, that's it. End of story."
  — Joanne’s second email [11:22]

• "Oh my God, do you think that every time she gets this voicemail, she gets all of her... office, ‘Oh my God, he called again!’"
  — Kristin [13:49]

• "He’s going to call the restaurant now!… The general manager of China Grill..."
  — Bert, narrating the saga [14:56–16:47]

• "China Grill... completely comp it for her. And they even give her free drinks the next time she's in."
  — Bert [17:20]

Timestamps for Key Segments

• 01:02 – The story premise: Darren and Joanne meet on JDate
• 02:45 – The bill-splitting debate; Darren declines Joanne’s offer
• 03:35 – Darren’s awkward email requesting $50
• 04:47–06:17 – Darren’s first demanding voicemail
• 08:19 – Joanne’s cool but firm email reply
• 09:06 – Darren emails his AmEx bill: “Do the right thing, Joanne”
• 10:34 – Darren threatens workplace involvement and legal action
• 11:06 – Joanne’s thorough and cutting response
• 13:46 – Yet another voicemail: “Just business at this point”
• 14:56 – Darren calls China Grill to intervene
• 16:47 – China Grill manager calls Joanne
• 17:20 – China Grill comps Joanne’s meal—case closed
• 18:17 – Listener Linda calls in: “He is a class jerk.”
• 19:13 – Story’s aftermath and viral status

Tone & Style

As always, The Bert Show brings humor, honesty, and a collective "can you believe this?" incredulity. The cast riff on the ridiculousness, swapping jokes, offering perspective on modern dating, and imagining the office’s response as this drama snowballs. Their relatable, conversational style keeps the cringe comedic and the story lively for listeners.

In Summary

This episode is a true case study in what not to do after a first date—showcasing entitlement, social cluelessness, and the line where assertive follow-up shifts into harassment. With real-life emails, voicemails, and a clueless protagonist whose actions made national rounds, The Bert Show turns what could be an infuriating tale into a masterclass in group comedy and cautionary storytelling.