Vault: One Of The Worst Dates Ever!

Summary

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.

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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.

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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.

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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

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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.

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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.

Transcript

[A]

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[B]

Did I talk too much?

[C]

Can't I just let it go?

[B]

Wish I would stop?

[D]

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[B]

The Birch Show. You guys are gonna absolutely love this. At first I didn't think it was true. I just thought it was kind of urban legend. But it turns out that everything I'm about to tell you is a true story. At least Snopes has looked into it and they said there is nothing that we can find that says that this is not a true story. Okay. All right. So as the story goes, Darren Sherman, who is a CEO of Regulatory Advisory Services in New York, it's a private financial consulting firm. High ranking dude. Really high ranking dude, okay, goes on J Date and finds a woman named Joanne he wants to go out with. Now, for those of you that aren't familiar with J date, it's basically match.com for Jewish people. Okay, okay.

[E]

Okay.

[C]

So because most Jewish people date within their religion, right, Bert?

[B]

I can't comment on that. I've only been Jewish for very convenient.

[E]

Amounts of time, save that.

[B]

I was.

[C]

Only Jewish through my bar mitzvah then once I got the gifts.

[B]

Jeff is right, though, there. I mean, and I think it's no different than in other religions. Also, sometimes you want to just date people within your own religion. So on JDate, these are people that are very serious about being Jewish. So they want to only date and have futures with people that are Jewish. Anyway, very small part of the story. So Darren and Joanne, they go out and they go to a place called China Grill in New York City. I have never been, but from what I understand, it's a really, really nice place in New York.

[E]

I think they have another one in Las Vegas that I've been to and it's awesome.

[B]

It's really good.

[E]

Yeah, super nice, fancy.

[C]

I've never been there, but it's like one of the celebrity spots.

[E]

Yeah.

[C]

Like in both cities. I think there might even be one in LA too.

[B]

So these two go out on their date and I guess have a decent enough time. But at the end of the date, and this is a key ingredient here, she offers to split the bill with him. And he says, nah, nah, nah, don't worry about it, I'll pick it up. Right.

[E]

I'm a big time guy from this private investor firm, I'll take care of it.

[B]

You know, I think most guys probably handle it that way. No, don't worry about it. I'll take care of this one. I'll see you again next week and.

[C]

Then we'll have sex and it'll be.

[B]

All worth it sometime. From the end of their dinner to the next morning, he was starting to think, you know what? That just didn't go so well last night. I know this, that there's not gonna be a second date happens. So when Joanne gets into the office, he has sent her an email already. And the email just says this, it says, sorry things didn't work out. I guess you changed your mind. Here is my address for the 50 bucks. And it has his mailing address. That's all it says. So I'm assuming at this point the bill came to $100, something dollars, and because he feels like it's not gonna work between them, or there's not gonna be another date, he's already saying, look, here's my address, send me a check for 50 bucks.

[E]

So something must have happened at the end of the night where she told him, like, I'm sorry, I'm not gonna see you anymore, or I'm not gonna go to bed with you, or whatever it was.

[B]

I don't know if that's true because I'm gonna read you an email in a couple of minutes here that pretty much, she says to him, I was really thinking about going out with you again, but since all this has happened, I can't. So at least in her mind there was a chance of a second date.

[E]

So she didn't close the door at the end of the day. Okay, I'm sorry.

[B]

Apparently she didn't close the door at the end of the date.

[E]

Gotcha.

[B]

So this was just his assumption. That's why he sends out the email. She looks at it and she's like, this is a little crazy, but doesn't respond to it. Just lets it go. So he goes back to his email, and he sees that he doesn't get a response, and he starts stewing about it a little bit, and he fires off a voicemail message to her, calls her on her phone, and leaves this voicemail message. This is real. Okay.

[F]

Hey, Joe and Darren. I was hoping you were going to do the right thing here, you know, disappointed, but I'm hoping you're going to turn around and do the right thing, because I don't want to really keep calling you and emailing you, you know, issuing you a summons. But it's your call for $50, you know, I suggest you do the right thing. You ate the food, you drank the wine, said you're gonna call. You never called. It's been two and a half weeks, so what do you want me to do? You know, you took advantage as far as I can see. And so you know my policy. It's, you know, first beat, we go dutch. You said you wanted to go out a second time, so I picked up the bill, end of story. But you never called me back after two and a half weeks. So I'm asking for the money. So I'm hoping. Gonna do the right thing. Be a mensch. And the next time you go around dating, you know, you know, be careful because don't leave guys on, which is what you did with me. So anyway, that is on the wayside. This is just business and $50, please. Put it in the mail and we're done. You never have to hear from me again. Otherwise, I'm just gonna, you know, keep on top of this. And I don't think you want me to keep on top of this. It's your call. Don't be cheap here. Just get it done, drop it in the mailonara. Which is what I'm hoping you're gonna do. Do the right thing here. Don't take advantage of people. You ate the food, you drank the wine, you didn't call back in two and a half weeks.

[E]

Okay.

[F]

Do the right thing.

[B]

Okay, so we're starting to piece things together here a little bit. Repeater guy.

[E]

Yeah.

[B]

So I guess the date ends. She says, all right, I'll give you a call in a couple of days. Two and a half weeks goes by, so obviously there's not going to be another date. Now this dude's feeling stiffed, I think.

[C]

What? Because if you read the. We could post the whole thing because somebody sent this out. Like, it got Posted on a blog in New York, and now it's making the rounds, like, you know, whatever, so we could post the whole thing. But it's a very long story. But the short version is they did go out, they had dinner, they went on a date. And she said at the date, according to him, she offered to pay.

[F]

And.

[C]

And then he said, no, you can get the next one. And she agreed. She said, okay. So that's where his. Okay, that's where his hiccup is.

[B]

That's the breach of integrity.

[C]

So there was no right on.

[E]

Okay.

[C]

There was no commitment to another date. There was no whatever. It was just kind of like, you get this and I'll get the next one, whatever. And she didn't like him. So when he started calling her and saying, hey, I had a great time last night. Let's do it again, she just didn't call him back. And we've discussed this on the air. What is it, two or three calls and then you just give up?

[B]

Let it go. Right.

[C]

Well, he didn't give up because he wants his $50.

[B]

So she listens to that very voicemail message, and again, she doesn't respond back to him. She walks into the office and this email is waiting for her. It says, joanne, I wanted to follow up on my email and call to you last night to ensure you receive my Messages for the $50. Please acknowledge by replying to this email that you will be sending me the 50 bucks. I hope you understand from my point of view. Thanks, Darren.

[E]

Okay, why do I feel like we're being led on to, like, some TV movie at the end of this? This is all some big promotion for something else.

[B]

No, there's not. There really isn't. Unless it's China Grill. She responds back with this email to him. Darren, I just received your emails and also your message from last night. I was away and am just sent getting back to it this morning. I had every intention of calling you and meeting to go out, 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. Please do not call me or send me another email. I would rather not hear from you at all. And for future reference, in the dating world, you may want to rethink the tacky approach about asking someone for money like that. Perhaps that is why you haven't met anyone or. Or have seen them again. So he's reading that and he is just Getting pissed, Right? So he cuts and he pastes his American Express bill into an email, and he only writes on it in bold letters. Do the right thing, Joanne.

[E]

No.

[B]

Yes.

[C]

Now, I think in his defense, the total bill actually comes to about 130 bucks. So he's letting her off.

[B]

He's just trying to be nice about it.

[C]

I'm guessing this guy, I'm just guessing, is like probably a 10% tipper. 50%. 50 bucks is that important to him? I'm guessing he's not throwing down the full 18%. So his whole bill came to like, let's say $145. He only wants 50 bucks from her. He's technically absorbing two thirds of the meal. Do the right thing, Joanne. I'm with you.

[B]

The email comes in. She's like, what is. What is this dude's problem? Doesn't respond back to it. Four hours later, he sends another voicemail message and he calls her back and he leaves this message.

[F]

Joan, this is Darren. She's calling to follow up on my email to you. It seems like you're sort of hiding behind emails. If you care to chat, reach out to me. I'm gonna, you know, flesh this out. And you can only hide so much behind emails. And so it's your call, but I'm going to flesh it out and, you know, reach out to your employer and issue the summons and, you know, going to call. You can hide behind the emails or you can drop the $50 bill that you owe me in the mail. My next call is going to be down to your employer, and I'm going to be going down to the courthouse very soon, soon, probably within the next.

[E]

Few days and issuing some garnish her wages for dinner.

[B]

He's going to call the employer and garnish the wages. Okay. She writes back to him. She doesn't want to call him, so she writes back an email and it says this. I'm truly sorry it didn't work out. You seem like a nice guy, but 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 the bill came and you declined. As far as I'm concerned, that's it. End of story. I didn't know that your paying the bill was contingent on me going out with you again. Once again, I think you need to look internally as to why things are not working out for you in the dating world. You'd mentioned that you had been burned several times, and I'm sorry if you feel that it has happened to you again, but perhaps it's your approach in dealing with others that leads to this. Dating and relationships and business are completely different. And there's not a quid pro quo for eating and drinking on a date. If this is how you think it works, perhaps you should consult a professional who could take care of all your needs. If I remember correctly, it was your choice to go out to dinner. I would have been just as happy to take a walk in the park to get to know you. With that said, please, please feel free to call my employer or issue a summons if you think that this will help. Your message has said that you will not drop this, and I am not one to be bullied or threatened. I have saved all your messages, and if you choose to go ahead with your threats, then I'll be more than happy to notify the proper authorities and get a restraining order. I will also let your clients and employees know about your erratic and bizarre behavior, which is certainly what she's doing now by posting these on the Internet. Darren calls her office again. No. He's so ticked off when he gets this email, he calls the office and leaves this message.

[F]

Joan, this is Darren's calling. I just got your email. Obviously, you know, we're at a crossroads. You know, I really would like to leave off in a somewhat leisurely way here, but I am expecting the money and really don't want to have to go above your head and, you know, contact your employer, tell them that you date JDating on JDate, and also issue you a summons at your job for just $15. I can do so, and I will. So it's your call whether you want to get a summons at work. And if your boss wants to get a phone call from me, your call for 50 bucks, I suggest that you pay because I'm going to, you know, I'm going to be on top of you. It's not right what you did, and so I'm not going to be taken advantage of, and so I'm not going to let it go. And so it's your call whether you want to pay up voluntarily or not. But I will be reaching out to your boss by end of day today if I don't hear from you. So it's your call, and I will be issuing a summons to your job for the money. So you ate the food, you drank the wine. Finally pay your dinner. Just business at this point.

[C]

Now I know why she didn't go out with him again. What a boring conversation.

[E]

Oh, my God. Do you think that every time she gets this voicemail, she gets all of her cube like office. Oh my God, he called again. He called again. She sends out like the company wide email and everybody's crowded around the speaker.

[A]

Listen to this.

[B]

Oh my God.

[C]

No work got done in that office that day. None is zero. Because they did. You know what they did is they just sat by her phone and waited for the little light to go big, right? Oh, yeah, somebody going, hey, yeah, listen, I just got a problem with my invoice. Oh, damn it.

[B]

Delete.

[C]

Next.

[B]

And this certainly does not perpetuate any stereotype about them meeting on Jay. I know, I know, right? That's not gonna help, right?

[E]

Yeah, exactly. Is fighting over 50 bucks.

[B]

So she gets that voicemail message and like you say, right? Everybody's probably crowded around listening, you know, 28 minutes goes by, he calls back.

[E]

Again and everybody's going touchdown again.

[C]

I wonder if this little incident right here is one of those wars that Mel Gibson was talking about between Darren.

[B]

And what's her name, you know, somewhere Mel's going. You see? See what I'm talking about? See what I'm talking about? 28 minutes goes by, she hasn't called him back. He leaves this voicemail message for her 28 minutes later.

[F]

Hey, sorry for any inconvenience. This is Darren's calling. I just got off the phone with the general manager of China Grill. I ask the person to reach out to you directly and you can just take it as you wish. If you want to settle the matter directly with China Grill and pay half of your share, it's probably the best way to go. So the person will be calling you up hopefully by end of day today. You can take a proactive approach and call them up directly if you choose to. I would encourage you to do that and just get this matter solved. You know, if we think this matters out, as I said, I'm going to be issuing a summons if we can't get anywhere. So obviously, you know, this doesn't benefit anyone. It's your call and sorry you're upset, but you know, it is what it is. It's really just business at this point. So, you know, obviously I'm going to go forward so hope we can clear the matter up and just part ways and it's your call. All is completely in your corner. What I outlined everything I'm gonna do and I'm gonna do exactly as I said. I think you see that now and it is just on your side whether you want to, you know, not do Anything and just hide.

[B]

You ate the food, you drank the wine.

[F]

Once, twice. So do it. You know, put some money where your mouth is. Look, I'm looking to settle this nicely, but you, you know, you're hiding and you're not acting right. So do the right thing. Bye.

[B]

Do the right thing, Joanne. All right, so he's. Now, he said he's called the China Grill, talked to a manager and said, here's what's going on. Here's the phone number of Joanne. Will you give her a call and try to settle this yourself? All right, Couple of hours later, Darren doesn't call back. China Grill. Now call Joanne.

[G]

Hi, Joanne, this is Carol Serena, the GM at China Grill. I understand there was a discrepancy with the bill today that we want split it between you and your friend Darren. If you could call me back at 2 1,088. I greatly appreciate it. And we'll get this all settled and taken care of.

[F]

Thank you.

[B]

So now she's got the restaurant on her butt also.

[E]

Well, I'm sure that he was badgering the restaurant ten times as much as he was badgering her.

[B]

No doubt, because she ate your food and she drank your water. Now, the good news is China, she calls back China Grill and tells them everything that's been going on, and they 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. But can you believe this dude?

[E]

He's wound so tight. It's like, you know, it's time to leave New York. When do you think that he is sitting there with all his friends? You know, when you have any sort of relationship drama going on, you sit around with your friends and you talk to them about it. And he's sitting there going, this girl, she won't pay the 50 bucks for my meal. You know? And do you think his friends are like, right on, man.

[B]

Yeah, because you get that 50 bucks. Because you surround yourself with people that are like you. So they're like, it's not your fault, dude. I mean, if she's gonna be like this, if she's gonna eat the food and drink the wine, she's gotta pay.

[E]

No, I don't think this guy has any friends. I don't think he has anything to do with his time.

[C]

I was gonna say, he's probably not sitting around talking to his friends because his friends all left years ago when he became the guy who split the bill using the calculator in his checkbook. Okay, my Share with tip is 2308. So I'm gonna need 92 cents back from that.

[D]

Thank you.

[B]

Hey, Linda. Good morning. You're on the Burt Show.

[G]

Hey, this guy's a stereotype, but I don't think it's the one you're using. But he is a class jerk. There isn't a judge on earth that would listen to half of that plea.

[B]

I would. I would almost like it to go to court so we can hear it on and watch it.

[G]

She needs to counter sue him for sexual harassment. You know, idiots like he have been trying to say that if they. If they pay, then you better play. And that isn't dating, that's prostitution. And she ought to be running him up the wires. She ought to be posting it on his company website. And oh, by the way, she ought to find out the dude's wife's name because, you know, that's going on too.

[B]

Well, he already knows. I mean, she posted all of this up online. I mean, and this email that has these voicemails in it and a transcript of everything that's gone down has been circulating now for about a week and a half. So he's got a scarlet letter on him now, right?

[E]

That is too funny.

[B]

And that is all a true story. So consider yourself lucky if you come out on the weekend on a date and this doesn't happen to you. You know, every Jewish person in the city right now is going, no, no, no.

[C]

First Mount Gibson, now Darren of New York.

[B]

The Bird Show.

[D]

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[I]

Are you.

[H]

Are you playing me off? That's what's happening, right? Okay, give it a [e-mail] Switch upfront.

[B]

Payment of $45 for three month plan. $15 per month equivalent required. New customer offer first three months only, then full price plan options available, taxes and fees extra. See mintmobile.com Acast powers the world's best podcasts. Here's a show that we recommend.

[I]

Hello, this is Jessie and Lenny Ware from Table Manners, a podcast direct from our dining table where we talk all things food, family, growing up. And everything in between. And everything in between. This season, we've had Reese Witherspoon reveal the greatest cookie recipe. We had Gary Oldman, who's freshly knighted. Sir Gary Oldman. Sir Gary Oldman. We did some singing with Gloria Estefan. And Jeremy Allen White has shared some culinary stories with us. And it's not just this series. We've had plenty of other brilliant guests where you can listen back to all the episodes. People like Cher, Dolly Parton, Kate Winslet? S, Paul McCartney, John Legend, Benny Blanco and Selena Gomez. We've had them all. And we fed them very. Come and listen to table manners. The podcast with me, Jesse Ware and Lenny Ware.

[B]

Acast helps creators launch, grow and monetize their podcasts everywhere. Acast.com.