Vault: She's got some strong leads to Chelsea Handler

Summary

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The Bert Show: Vault – She's Got Some Strong Leads to Chelsea Handler

Date: July 8, 2026
Hosts: Bert, Jen Hobby, Show Cast
Main Theme:
The quest to secure a face-to-face meeting with comedian Chelsea Handler during her visit to town, and the playful, determined antics of Jen Hobby and the show’s team in trying to make this fandom friendship a reality.

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Episode Overview

This episode centers on Jen Hobby’s determined (yet so-far fruitless) bid to meet Chelsea Handler, who’s in town for two sold-out shows. The Bert Show team and listeners brainstorm and share creative, often hilarious strategies for getting Jen that coveted introduction. The conversation is full of good-natured ribbing and camaraderie, capturing the show’s signature vibe of humorous, relatable struggles with a dash of celebrity-obsessed fun.

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Key Discussion Points and Insights

1. The Challenge of Meeting Chelsea Handler

• Status Update:
  • Bert laments that despite listener enthusiasm, no concrete leads have materialized for Jen to meet Chelsea.
  • Multiple listeners echo Bert and Jen’s admiration for Chelsea, but can’t provide a direct connection.
  • The difficulty of accessing Chelsea is compared to celebrity meets in general, with Jen noting:

    "It shouldn't be as difficult as this has been this week. I mean, it's really not like we're talking about Oprah."
    — Jen Hobby [05:03]

2. Handler’s Event Schedule Complicates Efforts

• Chelsea Handler is playing two sold-out shows at the Fox Theatre (8pm and new 5pm slot).
• The team discusses Chelsea’s scheduled book signing at the Outwrite Bookstore as a potential, albeit chaotic, opportunity for a meet-and-greet.

  "But that's going to be crazy packed. There's no place to make best friends."
  — Bert [03:26]

3. Avoiding “Superfan” Energy

• Bert is adamant that, to foster genuine friendship, Jen must avoid looking like a superfan in a book-signing line.

  "If we are destined to be best friends, then I can't be a fan. Like, I'm not a super fan… then she'll see me as a fan and not a friend. Duh."
  — Bert [04:31]

• The cast jokes about staging Jen’s presence at the bookstore, so it looks casual—buying a gift for a friend, rather than stalking a celeb.

  "Can't you just be happening to be shopping at Outwrite, which is where you normally go… And then, what a surprise. Chelsea's here also."
  — Jen Hobby [04:47]

4. Realistic “Access Points”

• The team assesses their lack of industry or Fox Theatre ties that could cut through red tape.
• The book signing remains the best path, but with odds stacked against them.

5. Listener Ashley's “Strong Lead”

• [05:27] Listener Ashley calls in with a promising offer: she bought a pre-sale book at Flying Biscuit Café and inadvertently scored what’s described as a “press area” spot (number 5 in line) for the signing.

• Ashley invites Jen to attend as her “friend,” which could get her backstage access with Chelsea and the press for photos and conversation.

  "The deal with 1 through 5 is that you get to sit in what they term the press area… you get to sit with the press, you get to hang out with Chelsea. She’s gonna spend a few more minutes with those people. Taking pictures, chatting, drinking coffee."
  — Ashley [06:14]

• The team expresses playful suspicion that Ashley is fandom-networking herself with Jen, drawing parallels to Jen’s own Chelsea quest.

• Ashley gamely responds:

  "I do want to be Jen's bff."
  — Ashley [06:59]

• They joke about their exclusive “press conference media section,” which nobody ever attends, poking fun at their relative “VIP” status.

6. Playful Banter & Closing Jokes

• The exchange is full of self-deprecating humor about friendships with celebrities, faux invitations, and invented media hierarchy.
• Notably, they riff about morning routines and getting “real close” as prep for the signing, ending in a typical burst of irreverent Bert Show energy.

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Notable Quotes & Memorable Moments

• On missed connections and the Chelsea obsession:

  "...if you get a chance to hang out with her, then will you call us and we'll come and meet you and we'll all have drinks before the show and it'll be so much fun. We'll all be BFFs forever. That's what most of the emails said."
  — Bert [01:55]

• On being a ‘real friend’ instead of a fan:

  "Like, I'm not a super fan. Like, I'm not gonna stand in line for an autograph at a book signing because then she'll see me as a fan and not a friend. Duh."
  — Bert [04:31]

• Listener Ashley’s Power Move:

  "She’s gonna spend a few more minutes with those people. Taking pictures, chatting, drinking coffee."
  — Ashley [06:14]

• On Chelsea’s Celebrity Status:

  "She's hotter than Oprah right now. Oprah's on their way out… Chelsea is on her way up."
  — Bert [05:19]

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Timestamps for Key Segments

• [01:39] Bert updates on the cold trail for connections to Chelsea.
• [02:27] Bert shares that some strong leads fizzled out.
• [03:26] Book signing at Outwrite Bookstore is discussed as the next-best shot.
• [04:31] Debate over being a friend vs. a superfan.
• [05:27–07:18] Listener Ashley calls in with her special “press area” invite for Jen.
• [07:28] Outrageously funny suggestions for getting close to Chelsea, wrapping with signature Bert Show humor.

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Episode Tone & Dynamics

• Relatable: The everyday struggle to connect with a celebrity hero is handled with lighthearted honesty and self-deprecating humor.
• Supportive and Playful: Team camaraderie and inside jokes abound, making it feel like a conversation among friends.
• Resourceful: Listeners and hosts both crowdsource, strategize, and seize on new opportunities as they arise.

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In summary:
This episode of The Bert Show is an energetic, laugh-filled ride through the bittersweet joys of fandom—highlighted by creative plotting, clever detours, and fans-turned-co-conspirators all trying to make one heartfelt Chelsea Handler introduction happen. Even if the mission remains unfulfilled (so far), it’s the journey, not just the destination, that brings listeners along for the Bert Show’s morning entertainment.

Transcript

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[Jen Hobby]

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[Bert]

Well, the trail has run a little cold I think. But yeah, I would love to meet and hang out with Chelsea Handler. She's gonna be here this weekend. She's got actually two shows at the Fox on Sunday night. Excuse me. She has an 8pm show that sold out. So now there's a 5 o' clock show and I have heard from a lot of bird show listeners but none that can really help me find her. Just a whole bunch of them that say we feel the exact same way as you do and we totally want to be her best friend. So if you get a chance to hang out with her, then will you call us and we'll come and meet you and we'll all have drinks before the show and it'll be so much fun. We'll all be BFFs forever. That's what most of the emails said.

[Jen Hobby]

We were really hoping some of you guys would know somebody that knows somebody that would be really influential in Chelsea Handler's circle. So somehow, some way we could get Jen a face to face with Chelsea this weekend. And it just hasn't panned out that way yet.

[Bert]

And I've gotten a couple of emails from people who have had some strong leads but no follow ups from them. So they reached out to the people that they knew that they thought either worked for her, worked closely with her or whatever. But I haven't heard any follow up. So it's probably that they haven't heard anything from their contacts. So it's still, I mean there's still, you know, a few days to get this done and I'm hoping that she'll be in town by Sunday. So you know, I could take her to my favorite brunch spot and we could just hang out, of course, get some food, you know, have some of those grapefruit rosewater martinis at Cafe de Soul and just like chill out and like become best friends. Cause that's how I see it happening professionally.

[Jen Hobby]

There's nobody at the venue that we know. Cause there's usually like somebody of a somebody that we sold out.

[Bert]

I don't know anybody at the Fox.

[Co-host]

We know people, but she's not responsive to them. Cause she sold out both shows.

[Bert]

Oh, both are sold out.

[Co-host]

A few tickets left for 5 o', clock, but for the most part sold out.

[Bert]

So she doesn't need to do any promotion.

[Co-host]

She's an Outright bookstore on Sunday.

[Bert]

I did get a couple emails about that because she's gonna do a book sign so I can try to go there. But that's going to be crazy packed. There's no place to make best friends.

[Co-host]

They were working with Tracy, they were hustling to make something happen there.

[Bert]

But I mean maybe you have some herbal tea with her at Outright, you know, because they have a whole bar there, you can have tea and coffee.

[Jen Hobby]

Well, I have a little excuse. Chelsea doesn't drink tea from a guy that has a little experience in this area. I think it would probably be a good idea for you to go down to Outright just to be there. Because if it's going to happen, it's going to happen. But see, Bert, it's the same way. It's the same thing that happened with me and Sanjay when we met. Initially, it was. It was like I knew where he was going to be and I was at the same time. And then, you know, you fast forward six months, and now we're, like, best friends.

[Bert]

And now he, like, doesn't know who you are.

[Jen Hobby]

I see him every day.

[Bert]

You don't even believe yourself.

[Co-host]

Do you see him in person every day?

[Jen Hobby]

Yeah, I see him in person every day.

[Co-host]

So you can reach out and touch him.

[Bert]

Doesn't count.

[Jen Hobby]

I mean, yeah. I mean, there's a screen in between

[Bert]

two of us, but I can touch

[Jen Hobby]

him and I have, you know that brush his cheek.

[Co-host]

You know that I give him some butterfly kisses.

[Bert]

Oh, God. Eskimo kisses with our lashes. I mean, in order. If we are destined to be best friends, then I can't be a fan. Like, I'm not a super fan. Like, I'm not gonna stand in line for an autograph at a book signing because then she'll see me as a fan and not a friend. Duh.

[Jen Hobby]

Can't you just be happening to be shopping at outright, which is where you normally go to shop for all your books? And then, what a surprise. Chelsea's here also.

[Bert]

You're buying me a gift at outright? Yes. See, I have this friend who's giving baby wives.

[Jen Hobby]

She'll be looking at me like, yeah, yeah, sure.

[Co-host]

Wink, wink.

[Jen Hobby]

It doesn't feel like to me, like, Chelsea, although she is a celebrity for sure that she's not, like, an untouchable celebrity. Like, it shouldn't be as difficult as this has been this week. I mean, it's really not like we're talking about Oprah.

[Bert]

Where are you? Where have you been living?

[Jen Hobby]

I mean, she's a big deal. I mean, she's a celebrity.

[Bert]

She's hotter than Oprah right now. Oprah's on their way out.

[Jen Hobby]

You out your mind, girl.

[Bert]

Chelsea is on her way up.

[Jen Hobby]

Like, hey, Ashley, good Morning. You're on Q100.

[Ashley]

Good morning.

[Jen Hobby]

Hi.

[Ashley]

Hi. How are you guys doing?

[Jen Hobby]

Good, thank you.

[Ashley]

Good. Well, I just heard you guys talking, and I happened to be eating at Flying Biscuit a few weeks ago and saw that they were having all this Chelsea Handler stuff and they were doing the pre sale, and so I was like, oh, well, this will save me time. I'll just buy the pre sale book here. And he goes, okay, congratulations. You're number five. Had no idea what he was talking about. She's doing a book signing. At the bookstore. And if Jen wants to go, she can be my quote unquote friend and stand in line number five mean.

[Co-host]

But that's the same thing. You're just gonna be the fifth person in line.

[Jen Hobby]

It's not. She was the one that is there. She just invited Jenn as a friend. Jenna had nothing else to do so she decided to go with her friend Ashley.

[Co-host]

But she's still gonna be in line with a hundred people. And Chelsea's gonna go. What's your name? Ashley. And then?

[Ashley]

Well, the deal with 1 through 5 is that you get to sit in what they term the press area. And they said it was like the little backstage. You get to sit with the press, you get to hang out with Chelsea. She's gonna spend a few more minutes with those people. Taking pictures, chatting, drinking coffee.

[Bert]

How do we know you are the coolest? Ashley is my new bff.

[Jen Hobby]

And Jen, you get to sit with the media. That is cool.

[Bert]

The real media.

[Co-host]

Hold on a minute, Ashley.

[Bert]

I also get media passes.

[Co-host]

Not radio people like TV people like Ashley. How do we know that you are not doing the same thing that Jen's doing to Chelsea Handler? To Jen. Like what if you just want to hang out? Like if I just get around Jen hobby, I could be her friend.

[Bert]

Nobody wants to do that.

[Ashley]

I do want to be Jen's bff.

[Jen Hobby]

We have a media section set up for a daily press conference that Jet Bobby holds. So we'll put you in the top three if you want.

[Co-host]

And you got plenty of seats because we send out tons of passes and nobody ever shows up.

[Bert]

That's really weird.

[Ashley]

Come on.

[Bert]

Totally helps my self esteem issues.

[Jen Hobby]

Jen, would this be something that you would be interested? Should I put her on hold? Would you hang out with us?

[Bert]

Yeah, let me get Ashley's number for sure.

[Jen Hobby]

Thanks Ashley.

[Podcast Host]

Thanks.

[Bert]

My new bff.

[Jen Hobby]

Awesome.

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[Jen Hobby]

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