378: The Wildest Celebrity Relationships Everyone Somehow Forgot ft. Joe Peacock

Summary

Pop Apologists — Episode 378

"The Wildest Celebrity Relationships Everyone Somehow Forgot"

Featuring Chan, Joe Peacock (Guest Host)
Date: August 5, 2026

Episode Overview

In this episode, Chan is joined by her friend Joe Peacock (filling in for Lauren, who's reporting from Italy) for a spirited, sometimes jaw-dropping rundown of celebrity relationships that pop culture has largely forgotten—but which clearly live rent-free in their minds. From shocking age gaps and unlikely pairings to hidden romances revealed years later, Chan and Joe dish on six infamous celebrity couples whose relationships “the culture has moved on from, but we have not.” They weave in personal commentary, highlight the power dynamics and social context, and expertly layer in the cringe, nostalgia, and genuine affection that makes this podcast a pop culture fixture.

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Key Discussion Points & Insights

The Purpose & Tone

• The hosts reflect on why certain celebrity relationships struck or stuck with them, especially those that involved wild age gaps or were out of character for the people involved.
• Chan: “Relationships we have not moved on from.”
• Themes emerge of power dynamics, industry culture, gendered double standards, and the long-term impact of formative romances.

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The Relationships Breakdown

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1. Patrick Dempsey & Rocky Parker

Timestamps: 03:48–13:39

Overview:

• At age 18, a young, pre-fame Patrick Dempsey began dating 44-year-old Rocky Parker, who was playing his aunt in the stage production, Brighton Beach Memoirs.
• They married when he turned 21; she was nearly 48.
• Parker already had children older and the same age as Dempsey.

Key Details:

• “My parents maybe have met, maybe haven’t. Patrick Dempsey certainly isn’t the big star he is now. He’s just being put on the map.” — Joe Peacock (03:56)
• Rocky became Dempsey’s manager, mentor, and romantic partner.
• They kept the relationship secret before going public; Dempsey worried about his heartthrob image.
• Parker: “I taught Patrick how to read and write, so...” — Quoted by Joe Peacock (11:37)
• Their dynamic went beyond a professional connection, raising questions about age, control, and vulnerability.

Notable Quotes:

• “That kind of age gap is striking.” — Joe (08:52)
• “I think he felt very vulnerable and lost and she was an anchor for him.” — Joe (09:31)

Memorable Moment:

• Patrick Dempsey later told Barbara Walters: “I think I needed a mother. There were a lot of negative things that I’m still undoing from it.” — Quoted by Joe (12:17)
• Rocky Parker filed for divorce 10 years after they met; she has since passed away.

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2. Jerry Seinfeld & Shoshanna Lonstein

Timestamps: 13:43–29:13

Overview:

• Comedian Jerry Seinfeld was 39 when he began a relationship with Shoshanna Lonstein, who was 17 when they met in Central Park.
• The romance became public after they were seen at a Knicks game.

Key Details:

• “She is literally 17 at the time. And he’s how old? 39. Oh my God.” — Chan & Joe (16:45)
• Seinfeld denied the actual age difference on Howard Stern’s show, dodging questions about her being underage.
• Media coverage at the time often played the relationship as quirky or “celebratory” (23:24), but retrospectively appears disturbing.
• Shoshanna later transferred colleges to be closer to Jerry in LA.

Notable Quotes:

• “The moment you talk to them and find out you’re in high school, that’s your cue to exit the conversation.” — Joe (17:18)
• “You would Never date a 17 year old? No.” — Jerry Seinfeld denying it, via Howard Stern call (21:24)
• “All through her college… That’s crazy.” — Joe (23:45)
• Power dynamics, gender roles, and media misogyny are discussed critically.

Memorable Moment:

• Howard Stern later joked, “Is that what I’ve got to do to meet a young girl—is have a candy bar on a string and walk around Central Park?” (24:24)
• The relationship lasted four years. Shoshanna later ran a successful fashion brand.

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3. Jake Gyllenhaal & Reese Witherspoon

Timestamps: 29:16–43:14

Overview:

• After her split from Ryan Phillippe, Reese Witherspoon dated Jake Gyllenhaal (five years her junior) for nearly three years; Jake became close with her two young kids.

Key Details:

• They met on the set of Rendition while she was newly single (he was an old friend through her ex).
• Jake, at 26 with no kids, “steps up” to be a loving presence in the family.
• “It is very endearing.” — Chan (34:56)

Notable Quotes:

• “Jake at 26 was like, I’d totally be willing to sign up and play stepdad.” — Joe (34:49)
• “Their little family outings… so cute. So endearing.” — Joe (35:16)
• On the relationship’s end: “This relationship did a number on him because reports point to Reese breaking his heart.” — Joe (39:34)

Memorable Moments:

• Jake Gyllenhaal takes Reese’s kids to a 5K while she gets the morning off—“I mean, is that him taking (the picture)? Yeah.” — Chan (35:53)
• Their break-up reportedly broke Jake’s heart, which, per Joe, “was his villain origin story,” leading into his later well-known romance with Taylor Swift.

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4. Ryan Gosling & Sandra Bullock

Timestamps: 43:20–47:16

Overview:

• Post Murder by Numbers (early 2000s), a then-21-year-old Ryan Gosling dated 37-year-old Sandra Bullock for two years.

Key Details:

• “She does look quite happy with it [Ryan]. He really does look, like, so young.” — Chan (45:09)
• Though the age gap was significant, Chan and Joe characterize it as “respectable and just a win for a woman” because Gosling was established and 21 (45:43).
• The breakup was amicable; Gosling later praised both Sandra Bullock and Rachel McAdams as the best girlfriends he’s had, citing Hollywood “pulling them apart” (46:48).

Notable Quotes:

• “Ryan Reynolds wishes he were Ryan Gosling.” — Joe (47:19)

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5. Ryan Reynolds & Alanis Morissette

Timestamps: 47:32–56:17

Overview:

• The pair dated for five years (engaged for two), meeting at a Drew Barrymore party; Alanis was already at peak fame while Ryan was still ascending.

Key Details:

• “He looks like a Chad who, like, eats chips all day.” — Joe (51:30), on early Ryan Reynolds
• The engagement broke off in 2007; Reynolds almost immediately began dating then wedding Scarlett Johansson.
• Alanis later said she went to therapy five days a week after the break-up, writing the song “Torch” in part about him.
• Joe: “She dodged a bullet for sure.” (53:12)

Notable Quotes:

• “Ryan Reynolds is a love addict.” — Chan (48:50, 56:03)
• “He leaves Scarlett Johansson for Blake Lively… has this man ever really been single?” — Chan (56:12)

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6. Andrew Rannells & Anderson Cooper

Timestamps: 56:35–58:43

Overview:

• Recently revealed: Rannells briefly dated Cooper when Rannells was 25 and Anderson 37, inspiring a subplot on Girls.
• Anderson Cooper played coy when asked about the relationship: “Wait, is that the guy Andrew Rannells is dating? I thought he was more of a Bill O’Reilly character…” (58:02)

Notable Quotes:

• “This is not like we forgot. We had no idea.” — Chan (56:50)
• The lack of photographic proof and secrecy is contrasted with the couples above.

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7. Cameron Diaz & Justin Timberlake

Timestamps: 58:44–63:14

Overview:

• Timberlake (then 25) began dating Diaz (34) soon after his split from Britney Spears.
• Their relationship started after meeting at the Nickelodeon Kids’ Choice Awards (he won “Best Burp,” previously won by Diaz).
• Broke up amid tabloid drama—Diaz reportedly confronted Timberlake and his future wife, Jessica Biel, at a party only a month after the breakup.

Key Details:

• “She looked very in love, and I’m sorry, but I can’t help but think that he has demons and he’s with this angel.” — Chan (60:27)
• They worked together on Shrek the Third and then Bad Teacher after splitting, indicating they remained professionally cordial.

Notable Quotes:

• “Time is the biggest healer of all though, because… they did Bad Teacher together.” — Joe (63:05)

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Notable Quotes & Memorable Moments

• “They were together for years. Get a load of this. He became best friends with her second son, the one that was his age, his contemporary… the way I would love to interview these boys.” — Joe on Dempsey & Parker (06:19)
• “I definitely think… now I want to know what his upbringing was like… did he not have a very stable home life…” — Chan on Patrick Dempsey (10:01)
• “It can shape you in a lot of negative ways if there’s a power dynamic that exists, which, like, exists in all of these…” — Chan on age-gap relationships (26:24)
• “I wonder if her [Jessica Seinfeld] and Taylor have shared notes [about Jake Gyllenhaal].” — Chan (31:25)
• “If Reese Witherspoon dumped me, I would never be the same.” — Joe (40:47)
• “Ryan Reynolds is a love addict… moves on very quickly… has this man ever really been single?” — Chan (48:50, 56:03)
• “She dodged a bullet for sure.” — Chan, on Alanis Morissette leaving Reynolds (53:14)
• “I will never look at Jerry Seinfeld the same again.” — Chan (63:32)
• “Jake and Reese… we have texture there now, thank God.” — Chan (63:40)

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Structural Timestamps for Listeners

• Patrick Dempsey & Rocky Parker: 03:48–13:39
• Jerry Seinfeld & Shoshanna Lonstein: 13:43–29:13
• Jake Gyllenhaal & Reese Witherspoon: 29:16–43:14
• Ryan Gosling & Sandra Bullock: 43:20–47:16
• Ryan Reynolds & Alanis Morissette: 47:32–56:17
• Andrew Rannells & Anderson Cooper: 56:35–58:43
• Cameron Diaz & Justin Timberlake: 58:44–63:14

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Closing Thoughts

• The hosts reflect on how revisiting these relationships brings both “dark places, but also some bright places” (63:40).
• They note the lasting impact of these formative celebrity romances on both the individuals involved and on the culture at large.
• Finale: “You and I are going to blast all too well the entire way home from this recording so we can just get back to homeostasis.” — Chan (63:50)

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Summary

This episode is an unfiltered, frequently hilarious, and sometimes mind-blowing re-examination of headline-making relationships everyone claims to have forgotten, but which outline larger trends in celebrity culture, gender, and nostalgia. Chan and Joe approach each story with a blend of curiosity, critique, and real empathy, punctuated by memorable quotes, original insight, and strong vibes. For anyone wanting to revisit—or re-contextualize—the wildest celebrity pairings of the last several decades, this episode is essential listening.

Transcript

[Joe Peacock]

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[Chan]

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[Joe Peacock]

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[Chan]

I was shocked when you brought up some of these relationships. And so, like, I'm kind of business, like, how are we not talking about these?

[Joe Peacock]

He meets a woman who is 44. He is 18. Her oldest son, though, Chan, is seven years older than Patrick Dempsey.

[Chan]

Wait, so she has a 26 year old son? So Jerry Seinfeld met Shoshanna Lonstein in Central park. She is literally 17 at the time.

[Joe Peacock]

And he's how old?

[Chan]

39.

[Joe Peacock]

Oh, my God.

[Chan]

Yeah. Howard Stern decides on air, he's like, I'm gonna call Jerry Seinfeld and ask him about this girl that people are saying, you know, it's 17. No. So I'm gonna play it for you.

[Joe Peacock]

But I think it's endearing that Jake at 26 was like, I'd totally be willing to sign up and play stepdad.

[Chan]

We need to play. All too well. Someone turn on all too well. Well, well, well. Everybody, if you are joining us, you will notice that I am not sitting beside my lovely sister. I'm sitting beside my husband's best friend, who I stole from him. The one and only Joe Peacock is back on the podcast, gracing us with his. His presence, his brain, his everything today.

[Joe Peacock]

Hey, fam. Happy to be back. Spent the whole week with Chan and excited to spend a few more days.

[Chan]

I know, I know. I was actually going to ask you, are we going on day eight of being together?

[Joe Peacock]

I think, yeah, we are.

[Chan]

Eight or nine.

[Joe Peacock]

Yeah. Yeah.

[Chan]

How are. How would you say we're doing this?

[Joe Peacock]

This throuple is functioning so in such a healthy way.

[Chan]

So healthy. I mean, it's like I think I was pretty closed off to a poly relationship. But after spending the week with you and our friends and now it's just you, me and Ben, I feel more open to it than ever before.

[Joe Peacock]

I feel so taken care of, so looked after. It's been great. Not sick of you yet.

[Chan]

It's been wonderful. But yes, everybody, Joe is here because Lauren is currently. She's still out of the country. I don't know if you've seen her Instagram post, but she is currently still beachside in Italy. So Jo is here to save the

[Joe Peacock]

day and charge on Lauren, our beachside correspondent.

[Chan]

Yeah, she's gonna be bringing, I'm sure, lots of pop culture tea from the Italian shores. Today we are going to be talking about relationships the culture has moved on from, but relationships we have not moved on from.

[Joe Peacock]

No, we are. We are still there. These are the kind of things, as you're going to bed and maybe can't sleep, that your mind wanders to and clings to.

[Chan]

Absolutely. And we have six of these to go through. We've got a work cut out for us today. And you came up with this episode. We were kind of putting our heads together, trying to think of what we could bring to the pop apostles. And I just, like, I was shocked when you brought up some of these relationships. And so, like, as I dug in to research them, I just. I'm kind of beside myself. Like, how are we not talking about these more?

[Joe Peacock]

Yeah. A lot of these couples feel like another lifetime ago, but the pictures bring you right back there. And they're just like, each picture truly is worth a thousand words. And I have about a thousand questions

[Chan]

when I look at each of them. Absolutely. Okay, so let's get into it. Let's. Let's begin. Okay, why don't you start us off?

[Joe Peacock]

Yeah. So this first couple, I found out maybe within the last year.

[Chan]

Oh, really?

[Joe Peacock]

And it stopped me in my tracks.

[Chan]

Chan, where were you?

[Joe Peacock]

I was at home on my sofa. It was too late, and I just started. I love American history as much as anybody.

[Chan]

Totally.

[Joe Peacock]

And so this one, we're winding back the clock to 1984. It's Patrick Dempsey.

[Chan]

You and I are just a twinkle in our parents eye. We're very young.

[Joe Peacock]

Yeah, totally. Totally. My parents maybe have met, maybe haven't. Patrick Dempsey certainly isn't the big star he is now. He's just being put on the map. He's 18, so this is about 20 years before he steals our hearts and Grey's Anatomy. Okay. And at 18, he enters in a very peculiar relationship.

[Chan]

Yeah.

[Joe Peacock]

Where is it set? A touring production of a Broadway play.

[Chan]

Oh, like a traveling.

[Joe Peacock]

Exactly.

[Chan]

Troupe.

[Joe Peacock]

They have these national tours. Now he falls in love with a woman who is playing his aunt in the play, and he is the nephew.

[Chan]

And this play is called. What is this play?

[Joe Peacock]

The play is called. It's a Neil Simon classic. I know that Chan and Lauren aren't theater galleys, girlies. So this may mean something to some of the pop apostles, but it's called Brighton Beach Memoirs and it's a Neil Simon classic. Neil Simon being a famous playwright more than you asked for.

[Chan]

Would I know anything else by Neil Simon?

[Joe Peacock]

Barefoot in the park starring Robert Redford and Bar. No. Jane Fonda.

[Chan]

Yeah. No, nothing.

[Joe Peacock]

Maybe he wrote the Odd Couple.

[Chan]

Oh, maybe another one I haven't. I didn't get the chance to see. But anyway, anyways. Brighton Beach Memoirs.

[Joe Peacock]

Yeah, so. And he meets a woman who is 44. He is 18 and they play aunt and nephew in the play. Her name. Are you ready for it? Rocky Parker.

[Chan]

Cute, cute.

[Joe Peacock]

Kind of love that.

[Chan]

Yeah.

[Joe Peacock]

She's a widowed mother of three.

[Chan]

Oh, she's widowed.

[Joe Peacock]

She's widowed. Okay, so she's been through it.

[Chan]

Yeah.

[Joe Peacock]

Her oldest son, though, Chan, is seven years older than Patrick Dempsey.

[Chan]

Wait, so she has a 26 year old son?

[Joe Peacock]

26 year old son. She also has a 17 year old son.

[Chan]

Hold on. Okay, wait, wait, wait, wait. They're doing this play. I don't know anything about what happens in the play.

[Joe Peacock]

They're doing this play. Presumably they have scenes together. She takes him under her wing, she becomes his manager. Romantic feelings get involved. And at 8, when he turns 18, they start dating.

[Chan]

I mean they're. But presumably they're dating before.

[Joe Peacock]

A hundred percent. Yeah, but then at 21, he marries her. She's 30. 48.

[Chan]

Three years later.

[Joe Peacock]

Three years later. Okay, can I just. The photos really say it all? So I'm going to show. Have you, have you seen this couple yet? I know.

[Chan]

That is. Talk about the odd couple.

[Joe Peacock]

100%. I mean this, this one like.

[Chan]

Oh my gosh.

[Joe Peacock]

Bizarre. And they were together for years. Get a load of this. He became best friends with her second

[Chan]

son, the one that was his age, his contemporary.

[Joe Peacock]

The way. I would love to interview these boys.

[Chan]

Yes. Wait, okay, so. And maybe you know this, maybe you don't. So they are romantically involved, theoretically, while they're in this production together or afterwards.

[Joe Peacock]

Theoretically. Who's to say? I have to have to imagine. So.

[Chan]

Yeah.

[Joe Peacock]

And then they keep their marriage secret for about two years and then they're very public about it.

[Chan]

So they don't become public until like he's 23, presumably. Okay, okay.

[Joe Peacock]

Both. Because I think the age difference. He's trying to, you know, get his career off the ground, be a heartthrob. That could be hard when you have a. Not to be ageist, but you know, 45 year old wife.

[Chan]

Right. Someone double your age.

[Joe Peacock]

Yeah, yeah. You're all of a sudden. Maybe not the heartthrob. To all these young girls if you're not single.

[Chan]

And wasn't he also kind of playing these roles where he was like this kind of lady killer? A little bit?

[Joe Peacock]

Yes. And not just lady killer, but particularly to older women.

[Chan]

Yes.

[Joe Peacock]

There was a great profile in the 80s in the LA Times about him and it said Dempsey's biggest concern at the moment is escaping the restrictive image of k. Cute kid, the sort of boy man that in movies at least some older woman may find attractive. In the film in the Mood, he played a 15 year old boy who ran off with a man's wife during World War II.

[Chan]

Oh my gosh. 15.

[Joe Peacock]

15. In Lover Boy, he plays a pizza delivery boy whose female customers, quote, are expecting something more than cheese and pepperoni, dare I say sausage, something spicy.

[Chan]

Was that, was that your own? No, that was, that was, that was.

[Joe Peacock]

Right, that was LA Times print and further, a little disturbing. In that profile, Dempsey talks about how he dropped out of high school to be in that touring production of the play. It's just where he found success.

[Chan]

So this was like his first go at acting. Basically.

[Joe Peacock]

He hasn't even graduated high school.

[Chan]

Okay, okay, okay. So this is like, I think that kind of changes things. Well, it doesn't really change that much, but it's, it's very telling, I guess, about the state of mind that he might have been in when he meets this older woman who's like experienced in the industry. She offers to be his manager. Right.

[Joe Peacock]

Yeah.

[Chan]

And then like they're, they're now like linked in a career sense and linked romantically.

[Joe Peacock]

Like he's just gonna take care of her. Yeah. It would just read different. I feel like I could totally understand being. I'm out on my own now and making alpha woman your age, maybe 10 years older.

[Chan]

Yeah.

[Joe Peacock]

But that kind of age gap is striking.

[Chan]

That is, I think that's the biggest age gap in our, in this, in this deep dive. And like, I don't think there's a

[Joe Peacock]

bigger one for sure. And we so rarely see it with. Going that way with men.

[Chan]

I was just gonna say. Yeah, yeah, okay. Yeah. Please tell me also, where was, was she known before this at all?

[Joe Peacock]

She wasn't really known and she never really became known.

[Chan]

Okay, okay.

[Joe Peacock]

She was in like a few plays, films. Her career never took off. She doubled down on coaching actors.

[Chan]

Oh, okay. So kind of literally grooming, mentoring, quote, unquote.

[Joe Peacock]

Bizarre. Yeah. And, but you know, Dempsey was very complimentary of her in this, this piece for the LA Times.

[Chan]

In the 80s.

[Joe Peacock]

In the 80s.

[Chan]

Wait, are they together at this point?

[Joe Peacock]

They're together at this point. He said Rocky has. I can't get over that name. I know Rocky has had a tremendous impact on my life. Dempsey said, I have a person who is fighting with me. I'm not alone. Thank God. I have someone on my side. And a lot of my strength comes from that. I mean that's like worship level. And also just speaks to. I think he felt very vulnerable and simp lost and she was an anchor for him.

[Chan]

I mean. Q, you're on your own, kid.

[Joe Peacock]

Totally.

[Chan]

I. Yeah, I definitely, I definitely think. I mean, now I want to know what his upbringing was like and did he not have a very stable home life or like you would think that your parents would be like, hey, yeah, let's take this a little slower. Let's. I mean the idea that there is a. There are two children that you are now the stepfather to, that you were one of them that you are the same age of and the other one that you are seven years younger.

[Joe Peacock]

Bizarre. Like, and he's best friends with her son. Is she making them dinner and bring them both dinner, sitting between them on the couch.

[Chan]

Right.

[Joe Peacock]

It. And also it's just like, don't you think he would have been interested in like he's. He's very attractive.

[Chan]

Yeah.

[Joe Peacock]

Definitely becoming a sex symbol and yet he doesn't want to wield that power to date, quote, unquote, very hot woman his age.

[Chan]

Yeah.

[Joe Peacock]

It's just, I find very interesting also,

[Chan]

just looking at it from her perspective.

[Joe Peacock]

Yeah.

[Chan]

And this just kind of occurred to me. Okay, so you're. You have these two sons. Right. You literally have a 17 year old son. The fact that you would then be attracted like you. If you are a mother to a 17 year old son, I have to assume that you're kind of like, they don't know shit about fuck. Like they are so like 17 year old boys in general are just like, you know, finding their way in the world. That's putting it nicely. So the idea that you would then be like attracted to somebody at that same mental level.

[Joe Peacock]

Right.

[Chan]

And like at life experience level is just so backwards to me.

[Joe Peacock]

She definitely seems like she has baggage too. I don't know, I'm playing armchair expert here. But maybe she, you know, is a widow.

[Chan]

Yeah.

[Joe Peacock]

Things are out of her control. 18 year old boy is also someone you can really shape, mold and control.

[Chan]

Right.

[Joe Peacock]

One of the most interesting quotes of that profile is what Parker, Rocky Parker said about him. Quote, I taught Patrick how to read and write, so.

[Chan]

Oh, My gosh.

[Joe Peacock]

I know.

[Chan]

So it was like he was. She liked the fact that he was. Exactly, yeah, exactly. Didn't know a whole lot about the world.

[Joe Peacock]

Very bizarre.

[Chan]

What?

[Joe Peacock]

Rocky filed for divorce from him 10 years after they met. So they were married for seven years. That's a long time.

[Chan]

And 10 of the most formative years of your life when you're going from 17 to 27.

[Joe Peacock]

Bizarre they held on that long. He later, after Grey's Anatomy fame, I watched this clip of Barbara Walters interviewing him.

[Chan]

Always getting to the bottom of things.

[Joe Peacock]

Totally. And you know, she would ask things so directly and she's really like, you know, you were married to a 48 year old woman when you were 18. What was that about? And he said, quote, I think I needed a mother. There were a lot of negative things that I'm still undoing from it. He said, quote, she had a son one year older than me. I just, I wonder if his. Because Patrick Dempsey has been married for, I believe, 25 years to his wife now.

[Chan]

Yes. Yes.

[Joe Peacock]

I would love to get her thoughts on it.

[Chan]

Yeah, I absolutely would love to get her thoughts on it. I believe her name is Jillian or something.

[Joe Peacock]

I think so. I swear that she was like his hair style.

[Chan]

Yes, yes. She's like a makeup artist or something.

[Joe Peacock]

And I believe they broke up for a little bit or separated, like, during the pandemic, but they, like, found their

[Chan]

way back to each other, which I love, I love to hear that.

[Joe Peacock]

I think that's the most romantic part of any story. But, like, I don't know, as Patrick's going to bed at night, I know I'm thinking about Patrick and Rocky. I wonder if he ever drifts to, like, his first young love.

[Chan]

I mean, can you also imagine if, like, your parent, you found out your parent had dated somebody that much older than them for that long, had been married to.

[Joe Peacock]

Yeah.

[Chan]

Married to that.

[Joe Peacock]

Yeah.

[Chan]

I, I now I, I am just so curious about, like, where were, where was his immediate family in that situation?

[Joe Peacock]

Like, totally.

[Chan]

Yeah.

[Joe Peacock]

Yeah. And how faithful he was to her throughout that relationship.

[Chan]

Yeah. As, as his star grew, you know.

[Joe Peacock]

Yeah.

[Chan]

Rose. Yeah. Okay. Wow. Anything else about Patrick Dempsey and Rocky Parker?

[Joe Peacock]

She has passed and may she rest in peace. Throat cancer, I believe.

[Chan]

May she rest in peace. Wow. Joe. Okay. Well, I wish I could say that this next couple was more positive, had, like, less of an icky feeling, but they certainly don't. And we are talking about Jerry Seinfeld and Shoshana Lonstein. You're listening to this podcast, so I know you've got a curious mind. Here's a helpful fact that you might not know yet. Drivers who switch and save with Progressive save over $900 on average. They make it super simple. Pop over to progressive.com, answer some questions and you'll get a quick quote with coverage options tailored to your choices. Plus you'll see which discounts you may qualify for, like the online quote discount or savings for paying in full. In fact, 99% of Progressive Auto customers earn at least one discount. See if you could save when you switch to Progressive. You'll feel good about making a savvy choice. Visit progressive.com and see if you can enjoy a little extra cash back Progressive Casualty Insurance Company and affiliates national average 12 month savings of $946 by new customers surveyed who saved with Progressive between June 2024 and May 2025. Potential savings will vary Am I the only one who feels like August is the perfect time to reset? Before life gets busier and the temperatures get lower, it's the natural moment to recalibrate. And for many people that starts with resetting their everyday wardrobe and adding more layers. Quinn's focuses on high quality essentials like Mongolian cashmere sweaters and ultra soft organic T shirts of all styles. Their pieces are beautifully tailored, built to last and transition from morning meetings to evening plans beautifully. And it's not just apparel. Quince also specializes in hotel quality bedding and bath, kitchen staples and thoughtfully designed furniture. I absolutely love my Italian leather travel case. I put all of my cosmetics in it and it's held up through so many different trips. It's just so gorgeous and I feel like a true adult whenever I pull it out of my suitcase. Upgrade your everyday Download the quints app for app exclusive offers or go to quince.comapologist get free shipping on your order and 365 day returns. Now available in Canada and the UK too. That's Q-U-I-N-C-E.com apologists. This was another relationship that I had no idea about. And until, you know, the last seven days.

[Joe Peacock]

Yeah, this one's pretty wild. Which is striking because their age difference is less and maybe half of what Rocky and Patrick were, but somehow it feels more glaring because it's recent and because the gender roles are in reverse.

[Chan]

Yes, I think the gender roles are

[Joe Peacock]

reversed and her being under 18 doesn't help.

[Chan]

Yes, doesn't help at all. So Jerry Seinfeld met Shoshanna Lonstein in Central park in 1993. I guess she was Rollerblading around the park, and he approached her and asked for her number.

[Joe Peacock]

So he's at the beginning of his Seinfeld fame.

[Chan]

Yes, but also beginning of a Seinfeld fame. But he's definitely a big deal.

[Joe Peacock]

He's a big, big deal.

[Chan]

Big, big deal.

[Joe Peacock]

Yeah. I mean, Seinfeld's probably the hottest show there is.

[Chan]

He's. And he's the hottest walk in Central Park. Yeah. Guy in it.

[Joe Peacock]

And she's in high school.

[Chan]

She is literally 17 at the time. And he's how old he is 39.

[Joe Peacock]

Oh, my God.

[Chan]

Yeah, he's 39. So reports differ on, you know, when they became romantic. According to Seinfeld, they didn't start dating until she. Turn.

[Joe Peacock]

It feels icky waiting for that green light though, too.

[Chan]

Yes. If you continue staying in contact with a person with romantic ideas in mind. That's creepy.

[Joe Peacock]

Totally. Look, there could be 17 year olds that you could mistake for, like, 20 year olds.

[Chan]

Yes.

[Joe Peacock]

But the moment you talk to them and find out you're in high school, that's your cue to exit the conversation.

[Chan]

To exit the conversation. And to say, oh, I just had my 39th birthday. You know what? This is not the one for me. Let's show Shawna rollerblade in peace.

[Joe Peacock]

Yes.

[Chan]

But no, he didn't. And I actually have quite a few clips here that I want to show because he gets. He gets a lot of negative press for this.

[Joe Peacock]

Really?

[Chan]

Okay.

[Joe Peacock]

I'm glad I didn't know, because it's the 90s.

[Chan]

It's the 90s. While it is. You know, that was a different time. People are. People are definitely shocked by this age difference.

[Joe Peacock]

I mean, because, I mean, even in the 2000s, you know, like a decade later, I feel like there are Rolling Stone covers of whether it's the Olsen twins or Lindsay Lohan or Hilary Duff. Like the countdown to them turning 18 and being like, boys, she's almost legal.

[Chan]

Yes.

[Joe Peacock]

And that just would never fly today.

[Chan]

Totally, totally. But I think the fact that he was so much older than her and she really was underage and then. And not famous, just a totally normal girl living in New York. Okay. So it all kind of comes to light because they're spotted together and they are photographed at a Knicks game. Okay. And Howard Stern actually calls Jerry Seinfeld. Jerry Seinfeld had just gone on Howard Stern, like, a couple weeks before that. And so when these pictures came out, or at least they were, you know, spotted together at the Knicks game, Howard Stern decides on air, he's like, I'm gonna call Jerry Seinfeld and ask him about this girl that people are saying, you know, it's 17.

[Joe Peacock]

No.

[Chan]

So I'm gonna play it for you.

[Joe Peacock]

So he's not even a guest.

[Chan]

Yes, you're right. Not even a guest. Howard Stern is just. And I'm not a Howard Stern. I actually barely know anything about Howard Stern. But he's going to come up several times in this deep dive.

[Joe Peacock]

Howard Stern's like, there's an underage girl in the building. Let me get on the phone.

[Chan]

Let me get on the horn. But I think at this time, Howard Stern was definitely known for. And people who are Howard Stern heads are going to be annoyed, because I really don't know. Like, I don't know all the context here, but what I was reading is that at the time, he was known for really asking all the questions, like he was.

[Joe Peacock]

And still.

[Chan]

And still kind of. And still absolutely is. Okay.

[Joe Peacock]

He'll ask his guests, like, what kind of panties are you wearing?

[Chan]

Yes. Yes.

[Joe Peacock]

When did you first lose your virginity?

[Chan]

I guess I appreciate that. And what we'll hear is, like, I appreciate him kind of putting the screws to Jerry Seinfeld about dating somebody younger.

[Joe Peacock]

Not just right, you know, not like

[Chan]

gross questions to girls.

[Joe Peacock]

Yeah, yeah. So fair.

[Chan]

Okay, everyone. So this is from a 1993 Howard Stern recording. And, like, him and his co hosts are just talking about the news that Jerry Seinfeld was at this next game with this very young girl, and they decide, we're just going to call Jerry up and see what he says.

[Joe Peacock]

Gary from Howard Stern's office, can you, if you're there, could you pick up for just a second? Howard wanted to talk to you. Give me the phone. Hold on. Hey, Jerry. He's still with that 17 year old. You there? Hey, Jerry, pick up, because we got to talk to you. Some people are calling in and say you're dating a 17 year old, and I got a bet going that you're not. Just pick up and answer this for me. He'll lie. He wouldn't lie. He won't lie to me. Well, if he's concerned about that. Jerry. Jerry towered. Hey, listen, come on the air with me for a second.

[Chan]

Come on.

[Joe Peacock]

Just come on the air with me for a second. We have a bet going here.

[Chan]

What's the big deal?

[Joe Peacock]

Just come back, talk about you and your date last night at the game. Gary was there. Hold on. She's out of breath. I don't know what he's doing. He was just with her. You're with you. You're not with a girl now, are you?

[Chan]

Jerry. Where is he? Jerry.

[Joe Peacock]

Jerry.

[Chan]

Jerry.

[Joe Peacock]

Yeah. Oh, there you are. What are you so out of breath for? I was doing my exercises. All right.

[Chan]

I want to interrupt. I didn't even want.

[Joe Peacock]

I would never bother you. You know I like to schedule guests and stuff. But I gotta know. This is really unprofessional, Howard. Is it really? All right, then I'll. Then I'll hang up. Any idea how this business works? All right then I'll hang up. Then I'll hang up. Should I hang up? Yeah. No, but I gotta ask you, was the girl 17 years old last night?

[Chan]

She's not.

[Joe Peacock]

Of course not. Seeing, I told you guys. How old is she? 18. No.

[Chan]

19?

[Joe Peacock]

No. 20? 16. Yeah. Maybe we're going the wrong way. Would you swear she's not? Because we got 900 calls from her friends saying that she was 17 years old. No. Oh, okay. See, I told you guys. He's not this stupid.

[Chan]

Am I?

[Joe Peacock]

How could you picture Jerry Seinfeld going to a high school and picking up his girlfriend or going to the parents house? Jerry would never do that. Would you ever do that? No, he wouldn't do that. You would Never date a 17 year old? No. Come on, Robin, I'm asking questions. So who were the people who called in dumb? Am I? Who were the people who called in Gary? Just assorted. Who are these people? No, really, seriously. Just assorted people. Who are these people? Just assorted people. But they were all. I mean, Gary said the whole damn garden was turning around. They weren't even watching the game. Jerry, she was incredible. I don't know where you got her. Nice girl. Yeah. Hey, and you were sitting with Rob Reiner and, and as y bell, huh?

[Chan]

Okay, we don't need to play the whole thing because it's just, it's kind of gross and whatever and they're just kind of shooting the shit. But I wanted everyone to pay attention to the fact that he says that she was not 17. He doesn't even say that she's 18. Well, very soon after this, an article comes out and it says high school sweetheart. For TV's Jerry Seinfeld, I'm going to read this to you. Hard to know just what might they have to talk about but 30 year old, but 39 year old Jerry Seinfeld has a new good friend called Gorgeous 17 year old high school senior Shoshana Lonstein. We initially assumed that they met on some sort of school trip, but a source told us that Seinfeld met her on A warm day in Central park about four weeks ago. Since then, they enjoyed dinners at Mezzaluna, an expensive Upper east side eatery, and a show which we assume wasn't the school play. Shoshana, a senior at the exclusive all girls Nightingale Bamford School on the Upper east side, plays varsity soccer and basketball and is president of the film club. So it's not like they don't have anything in common. Seinfeld, whose people wouldn't call us back, and Shoshana were spotted together at Tuesday's Knicks playoff game. He vorociously denied that she was 17 on the Howard Stern Show. He was almost right. She will be 18 tomorrow. And Shoshana confirmed to us that she was, in fact, the comedian's mystery date. Sad as it may be, if Jerry wants to see her in the fall, he'll have to travel to D.C. or return to the campus comedy circuit. She's going to George Washington University. As far as we know, they won't be going to senior prom together.

[Joe Peacock]

Oh, God.

[Chan]

Can you believe that?

[Joe Peacock]

No. It's crazy how celebratory that publication.

[Chan]

I know. Like, it's a girl gorgeous high school

[Joe Peacock]

senior child bride for Jerry Seinfeld.

[Chan]

Yes. Isn't that shocking? And people were outraged, but, yeah. So, you know, this is a lot of buildup about the initial start of their relationship, but they go on to date for four years.

[Joe Peacock]

I mean, all through her college chance.

[Chan]

Yes.

[Joe Peacock]

That's crazy.

[Chan]

She transfers from college in on the east coast to UCLA to be closer to him.

[Joe Peacock]

That's so sad. I wonder what her parents thought.

[Chan]

Oh, I already know. Her parents were, like, Seinfeld fans.

[Joe Peacock]

Oh, my God.

[Chan]

Yeah. They were not.

[Joe Peacock]

Like, this is the best thing to happen to our daughter.

[Chan]

Yeah.

[Joe Peacock]

I mean, this isn't the first time something like this has happened to, like, a king in the arts. Elvis Presley. I think his wife was a 14 when he met her.

[Chan]

Yes.

[Joe Peacock]

You know.

[Chan]

Yes.

[Joe Peacock]

Something. Yeah. That is just so icky, though.

[Chan]

Well, and I mean, just hearing him deny that she was 17, I mean, it's just. It's so gross to me.

[Joe Peacock]

I love that they were taking him to court over it.

[Chan]

I agree.

[Joe Peacock]

Different time in media.

[Chan]

Yes.

[Joe Peacock]

Yeah.

[Chan]

And so, like, later on how he goes back on Howard Stern, and Howard Stern, like, presses him even more. This is gross. But he says, you know, is that what I've got to do to meet a young girl is a. Have a candy bar on a string and walk around Central Park?

[Joe Peacock]

So does Jerry cop up to lying to Howard about it, or.

[Chan]

I don't I don't know exactly. But I think that it's just kind of like. I think Jerry has a real, like, has a bad taste in his mouth for getting all the. All the. All the heat for it. And what I also saw as I was trying to research more and more of this, it was actually very hard to find those clips that, like, a lot of this relationship has been scrubbed from the Internet.

[Joe Peacock]

Yeah. Which is a thing you can do if you have enough money.

[Chan]

Yes. I mean, Howard Stern also, like, goes on to sing a song with this other person named Janice Iplin or something that's like, about. It's a whole, like, spoof song about the fact that Jerry Seinfeld dating this, like, 17 year old or this girl. 17. They met a stand up.

[Joe Peacock]

You think he'd be dragged anywhere for that.

[Chan]

Right. But I think he was also just very beloved by people.

[Joe Peacock]

Right.

[Chan]

So they broke up in 1997 after a four year relationship. They. But they were on red carpets together. Do you want to see pictures?

[Joe Peacock]

Yeah. Yeah.

[Chan]

Great.

[Joe Peacock]

Did she ever give any interviews after the breakup?

[Chan]

Not that I could find. So she went on to run a fashion brand.

[Joe Peacock]

Oh, wow.

[Chan]

And marry and everything. And I think that it would honestly, like, blow back on her a lot. I don't know. People are just like. Some people are big. Jerry Seinfeld, like, apologists. Like, he's just like, he can be very beloved. I feel like in our culture.

[Joe Peacock]

Yeah.

[Chan]

But like, there's them at some red carpet.

[Joe Peacock]

She's gorgeous, and she doesn't look far off from his current wife, Jessica Seinfeld. But that is just so young, isn't that so?

[Chan]

Yeah.

[Joe Peacock]

It's crazy.

[Chan]

I think what I realized, like, with this relationship and with the Patrick Dempsey relationship that I believe are like the youngest and the craziest age disparities, just the years that you are, you know, exiting teenage. The teenage world and kind of entering your early twenties are just so formative. And if you have a long term relationship with somebody who's so much older than you.

[Joe Peacock]

Right.

[Chan]

It can shape you in a lot of negative ways. If there's a power dynamic that exists which, like, exists in all of these because, you know, there's just this person's just so much older than them, and it can just. It can be bad for your brain, I think if you just, if, if. If you date these people for far too long and then you kind of, like, lose out on some of your, like, youth because you were, like, dating this older person, you know, for so long.

[Joe Peacock]

Right. And that older Person, presumably, is not going to want to partake in all these kind of, like, youthful adventures that are hallmarks of being.

[Chan]

Yeah.

[Joe Peacock]

18 and 20. And I think it can feel very tempting at that age to be like, oh, I'm such an adult now, because I'm swimming in these circles, going to these places for dinner. But to your point, like, the. There's only a finite period of being young where you can kind of be reckless and do really fun, adventurous stuff that this older person's just not gonna be your wingman for.

[Chan]

Absolutely. And, you know, and, like, people who are your age can also do damage on you. Of course. But I just think. I think that the older people in this situation should realize that, like, people who are a lot younger than them should be, like, with their peers, and they should be having these formative experiences, learning about the world and themselves, like, kind of on their own terms and not through the eyes of just, like, a much older person who's already has, like, such an established way of thinking about life and everything.

[Joe Peacock]

Right. You know, what on earth were they talking about? Like, I think age gap relationships can feel more natural when you're older than, say, like, 26. Of course, when you're both kind of just adults.

[Chan]

Yes. When you have, like, a developed brain and, you know, the way you think about the world.

[Joe Peacock]

Yeah.

[Chan]

Yeah.

[Joe Peacock]

I wonder if. Not that Jessica, his wife, needs to answer for Jerry's crimes, but just that, like, you know, he's. She's his partner now. I wonder if they've had conversations about that where she effectively was like, what was that?

[Chan]

Or now that they have children that are, like, the age of, you know,

[Joe Peacock]

totally like, of Shoshanna. Yeah.

[Chan]

So I guess they did break up due to just, like, this, the public, you know, scrutiny. And also, I think that Jerry Seinfeld, from the reports that I read, did not really want her to have her own career endeavors. In fact, I heard that he said something like, I have enough career for the both of us. So. But, you know, Shoshana wanted to go on and start her own fashion thing, and I think she has a pretty successful brand nowadays. So. Anyway, crazy, though, I'm curious, is Jerry

[Joe Peacock]

Seinfeld, does his current wife and he have a large age gap as well?

[Chan]

They do. They have an age gap of 17 years.

[Joe Peacock]

Oh, wow.

[Chan]

Yeah.

[Joe Peacock]

Okay. So it's actually. That's not far off from his age gap with Shoshana.

[Chan]

Right.

[Joe Peacock]

But I think their union is more appropriate because I believe the two of them got together more when they. When she was an Adult, right?

[Chan]

Exactly.

[Joe Peacock]

Yeah.

[Chan]

Yeah.

[Joe Peacock]

It's a completely situation. An adult, but a very new adult.

[Chan]

Yeah. And I mean, he was over like half her age. He was like double her age and then.

[Joe Peacock]

Yeah.

[Chan]

With Shoshana.

[Joe Peacock]

So. Yeah.

[Chan]

Okay, now let's move on to the next one.

[Joe Peacock]

This is definitely going to be a cozier relationship. Not as salacious at all. This is actually one of my favorite Hollywood pairings. Didn't last, didn't take. But this is Jake Gyllenhaal and Reese Witherspoon.

[Chan]

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[Joe Peacock]

Two people that are still very much in the public eye now. But I think we often forget that they had a, I think close to three year relationship.

[Chan]

Absolutely. It's. Once again, I did not know about their relationship until, you know, we were doing this research also. It made me realize just how incestuous the Hollywood circles are.

[Joe Peacock]

Totally.

[Chan]

Everybody has dated each other. Yeah, like, everybody has, like, you know, like, it's just like the Jen Aniston, John Mayer, Reese Witherspoon, Taylor Swift, like, Jake Gyllenhaal. Like, it's just like all of these Venn diagrams, like, start to overlap.

[Joe Peacock]

And of course, like, some exes are on good terms, but I have to imagine there's a lot of exes who, it's like, you know, when someone's putting together a movie, they're like, okay, you know, we could have Jen Aniston in this and you know, another famous actor. But like, maybe they're like, oh, no, we can't because they used to date and they're on bad terms.

[Chan]

Yes.

[Joe Peacock]

I don't think this couple is. Is like that. They've had nothing but nice things to say about each other. And yet still I wonder if Rhys would want to do a movie with Jake.

[Chan]

Right. Or what. Or what she thinks when. You know all too well. 10 minute version came out.

[Joe Peacock]

Totally. I wonder if her and Taylor have shared notes.

[Chan]

I hope they have.

[Joe Peacock]

So Rhys met Jake. This is another bit of an age gap, but very, very appropriate. Rhys was 31 and. And Jake was 26.

[Chan]

Okay.

[Joe Peacock]

Love to see it.

[Chan]

Yeah. But that's. That's a healthy. That's great.

[Joe Peacock]

That's a total healthy.

[Chan]

Yeah.

[Joe Peacock]

They met on the set of the movie rendition. They didn't share a lot of scenes together. It's a lesser known movie, but they were doing reshoots in LA and they. This is just six months after Reese has announced her separation from Ryan Felipe.

[Chan]

Wow. Which. A relationship that, you know, everything there is to know.

[Joe Peacock]

Formative to us.

[Chan]

Yeah.

[Joe Peacock]

I'm still kind of rattled by it.

[Chan]

Yeah.

[Joe Peacock]

This is one your. Your listeners may remember that I changed our desktop screensaver at home to Rhys and Ryan forever when they broke up. Like, that's a moment where I know where I was when I heard that news. It was so sad. And then later, maybe when I was in high school, I remember we played a game, Balderdash, and it was like, if you could change places with any celebrity, who would it be and why? And everyone knew the card that I had wrote because it was, I would change places with Ryan Felipe because I would throw myself in front of a train for what he did to reach out.

[Chan]

And everyone, this is why we are so lucky to have Joe Peacock on the show. Just take a minute.

[Joe Peacock]

Thrilled to be here. What was so, so interesting is I read that Jake was an old workout buddy of Ryan's. So Reese had like kind of known him and thought he was kind.

[Chan]

Yeah.

[Joe Peacock]

They didn't have a ton to do together in this movie, but they met during reshoots in la.

[Chan]

Yeah.

[Joe Peacock]

And a source, according to People, said Jake went and reintroduced himself to Rhys. And from there, what a friend of Witherspoon's calls. Their little flirtation just took its course. Things slowly progressed. It was never something she thought would happen from the start. She just kind of developed this little crush over time. And I actually have a photo from the set of that movie that they were interacting with. Her character is pregnant in the movie and this is him giving her a little laugh. Don't you kind of love that.

[Chan]

Could they be any cuter?

[Joe Peacock]

I know just that look in her eyes.

[Chan]

And like, I mean I. I say this as somebody who. Yeah, like I. I find Jake Gyllenhaal to be kind of irresistible even present day.

[Joe Peacock]

Alarmingly so. I was listening to, I think it was his podcast interview with Dax Shepard. And I tell you, I had to take that interview in about 15 minute increments.

[Chan]

Yeah.

[Joe Peacock]

So that I could listen to all too well in between and just kind of bring myself back down.

[Chan]

Like, it's like splashing cold water on your face.

[Joe Peacock]

Totally like, Joe, you can't go there. Not go there.

[Chan]

I will tell you that. Recently he was spotted in my neighborhood where I live.

[Joe Peacock]

Jake.

[Chan]

Jake was. Yes. In fact, a friend of mine was passed by him and she called me. She was actually on my way to my house and she was like, Jake Gyllenhaal is around. And I dropped everything and ran in her direction. I'm just missed him. But yeah, it just. And I. The siren song. I mean we just saw the Odyssey. Like it's just. It's strong. It's strong. So sorry. That picture just really awoke some things for me.

[Joe Peacock]

Jake Gyllenhaal is the. The siren song. He's God tier cute, hot. Yeah. And what was interesting is, is Rhys has two kids at this time. Ava is seven and Deacon is three. And Jake has no kids. He's 26 years old. And it's just kind of, I don't know. And I hope this is not like you know, patting a guy on the back for quote unquote, babysitting his kids.

[Chan]

Yeah.

[Joe Peacock]

But I think it's endearing that Jake at 26 was like, I'd totally be willing to sign up and play stepdad.

[Chan]

Joe, I'm 100% right there with you. I think because we know a lot of 26 year old men, you and I have experience with 26 year old men of this world. I think that the fact that he was like very interested in a woman who had two kids who just had a much more like not 26 year old life.

[Joe Peacock]

Right, right.

[Chan]

I think it's like, it is very endearing.

[Joe Peacock]

The photos of their little family outings. Deacon on his shoulders. There are multiple pap walks of he holding Deacon's hand while they go get coffee.

[Chan]

We need to play all too well. So someone turn it on all too well.

[Joe Peacock]

I would love to just have a sit down with Deacon to talk to him about those coffee runs. I'm just gonna show you a little bit More. It's so cute. So endearing. Now get a load of this. Reese and Jake and the kids took a vacation to Martha's Vineyard. And Jake gave Reese the morning off and took the kids to go do a 5k.

[Chan]

Are you kidding me? I mean, is that him taking.

[Joe Peacock]

Yeah, it's him taking the photo of Ava crossing the finish line.

[Chan]

Do, do, do, do. I can't look at anymore.

[Joe Peacock]

And my favorite photo of theirs is probably of them at Coachella and him just cradling her. I just think this shows that Jake Gyllenhaal was such a soft place to land.

[Chan]

Yeah.

[Joe Peacock]

After Ryan cheated on her.

[Chan]

After the Unspeakable. You love that he's a slight. More slight man. Right.

[Joe Peacock]

I mean, he's definitely taller than Rhys because Rhys is so short, but yeah, I don't think he's, like, super tall.

[Chan]

All I'm saying is he looks. He looks quite broad in that photo.

[Joe Peacock]

Well, she dated him when he was making the box office bomb Prince of Persia. And we know that because it was supposed to be, like, a big hit back when Disney was kind of was doing these big action films like Pirates of the Caribbean. Okay, I don't have the photo, but he visited her on the set or. Sorry, excuse me. She visited him on the set of Disney's Prince of Persia. Chan. Do you know how down bad you have to be to travel to, like, Morocco to go visit your boyfriend in dress up for Prince of Persia.

[Chan]

Oh. Oh, no. Beyond. I mean, and I understand why he's taking her kids to do a 5K.

[Joe Peacock]

Insane.

[Chan]

I mean, so she was fresh off the divorce, and all of a sudden, this Prince Charming, totally five years her junior, is, like, ready to be, like, ready to be stepdad number one. The dad who stepped up.

[Joe Peacock]

The dad 100%. And he's ready to just join this domesticated life of hers. In fact, in an interview with InStyle magazine in 2009, I think we'll all remember, she said, Jake is a great cook. He does a lot. We spend the weekends outside LA in Ojai, where I have a farmhouse. Readers. Where she will later marry Jim Toth. But. And she has offloaded that property. Probably just too many memories. Quote, we have chickens and we grow cucumbers and tomatoes. I love it. It reminds me of where I grew up in Tennessee. And him, in another interview, said, I've learned so much from the kids in my life, and somehow they just become the center of your life and the way you look at things. Obviously, I exist in my girlfriend's world. And my sister's world in a different way. But it's opened my heart, and I feel much more grown up and want to be grown up as a result of it. Good God.

[Chan]

Good God. Wow. I mean, I think it's just. It's truly the way that he is so, like, all in on her life. It's not like, oh, yeah, you've got these two kids, but let's get away for the weekend. You know, let's leave them with the nanny. It's like he's all in on the family. Family show, you know, the Reese Witherspoon Single Mom Life 100.

[Joe Peacock]

And, like, I'm having trouble thinking of another Hollywood relationship where we've seen that guy step up and do that.

[Chan]

Totally.

[Joe Peacock]

To your point, with. With Jerry and Shoshana, a lot of these guys just want their wife, or. Sorry, their partner to be kind of a trophy or a wallflower slot in

[Chan]

exactly where they needed them to be.

[Joe Peacock]

Exactly. They're threatened by another career, let alone kids.

[Chan]

Kids, yeah.

[Joe Peacock]

And also with Jake, I think for most of your listeners in the last 15 years, we've just seen him date much younger. And so that's why this is just, like, so attractive. And what could have been.

[Chan]

Do you think there was. I don't know, like, now I kind of want to just get into the. To psychoanalyzing Jake Gyllenhaal. Like, do you think that he was corrupted? Like, do you think that Hollywood just kind of got to his head and, like, and then he just kind of became this total womanizer? It's hard to reconcile this right. With the movie star in me.

[Joe Peacock]

I'm. I'm so with you. But, Chan, what do we always say when that woman on Martha's Vineyard read you down for your Faith and Tim shirt? And I said, chan hurt people. Hurt people. I think this relationship did a number on him because reports point to Rhys breaking his heart.

[Chan]

Oh, shut up.

[Joe Peacock]

He was ready for marriage, allegedly, and she was just not. She couldn't. She allegedly couldn't give all of herself to him, and she wasn't ready for that, so she broke his heart.

[Chan]

Wow.

[Joe Peacock]

She told. Yeah, yeah. Around the same time of their breakup, she told Parade that she wasn't sure she would ever remarry. Quote, family is all we have in life, but I don't know how I feel about marriage. She said, obviously, I'm not far enough out of being married to think about doing it again. And so I think that was his villain origin story, because, you know, he talked about how he wanted to be so grown up. Well, what did he do after that relationship? He went in all too well. Taylor Swift, so grown up. And he thinks. He thinks he's an original doing it. Right.

[Chan]

Right. You know, wow. Hurt people. Hurt people indeed. And that, that is one of our mantras. We, you know, we say it on the regular when we're together and, you know, it's something I have to repeat to myself a lot.

[Joe Peacock]

I mean, if Reese Witherspoon dumped me, I would never be the same.

[Chan]

Especially when you're like. Yeah, no, it's just I. I'm actually at a loss for words. How long were they together for?

[Joe Peacock]

I think they were together about two and a half to three years.

[Chan]

Well, I mean, that's a. It's a lot of time.

[Joe Peacock]

A lot of time. And you know that. That photo of him taking a photo of her kids crossing the finish line at the 5k. He is thinking this is going to be a permanent memory that, you know, he's going to be in these kids lives forever.

[Chan]

Was it fair to the kids for her to break up with him?

[Joe Peacock]

It wasn't fair to us.

[Chan]

Wasn't fair to us. Certainly. How quickly after this was, was the Taylor Swift dalliance?

[Joe Peacock]

It's a great question. So this relationship ended in late 2009. Red came out. I was on my mission. With your husband. Yeah, Red came out in 2012. And so I'm gonna say this is probably a year to two later.

[Chan]

Wow, that's.

[Joe Peacock]

I could actually find the timeline, but yeah.

[Chan]

So he has a pretty swift fall.

[Joe Peacock]

Yeah, yeah, yeah. No pun intended.

[Chan]

No pun intended. Okay, well, sorry. Actually, one more thing. Doesn't also Reese then remarry, though, pretty soon thereafter, like the next relationship she's in. She does. Isn't that with Jim Toth?

[Joe Peacock]

It's with Jim Toth, yes. I don't think she dates anyone in between.

[Chan]

Yeah, but. And I think her and Jim Toth got married.

[Joe Peacock]

Yeah. Okay, so she began dating Jim Toth in 2010. So just less than a year later.

[Chan]

Yeah.

[Joe Peacock]

And then less. And then in 2011, she marries him.

[Chan]

Yeah.

[Joe Peacock]

At that same farmhouse in Ojai.

[Chan]

Right.

[Joe Peacock]

Where she spent, no doubt, countless weekends being like, she's.

[Chan]

She. She dated Jake Gyllenhaal longer than, you know, the duration of her meeting Jim Toth and marrying him. Right.

[Joe Peacock]

Because it's been two and a half years.

[Chan]

I mean, that's a slap in the face, you guys. This actually sheds a lot more light on the pain that Jake Gyllenhaal was in at the Time of. Of all too well.

[Joe Peacock]

And Taylor Swift. We're not saying it makes it right.

[Chan]

It doesn't make it right, but it does. It. It adds texture.

[Joe Peacock]

Yeah, it adds texture. People are not the worst relationship they've been in.

[Chan]

We always say that about you.

[Joe Peacock]

One thing I love, and I couldn't find the exact quote, but I never forgot it, is the writer, director Nora Ephron of youf've Got in Seattle. She was just, like, going off about divorce. Maybe it was in one of her books, but she said Reese Witherspoon had a textbook divorce. She never dated anyone inappropriate. And I think she really liked the two of them together.

[Chan]

Yeah, I guess so. Love Nora Ephron, shipping.

[Joe Peacock]

Reese Witherspoon, 100%.

[Chan]

Okay. I want to get into now another relationship that I think we've definitely forgotten about.

[Joe Peacock]

Okay. I'm excited. Who's this?

[Chan]

This is the relationship between Ryan Gosling and Sandra Bullock. Okay.

[Joe Peacock]

Oh, my gosh. I forgot about this.

[Chan]

Yes, yes, yes. These two. And I mean, I just have to say, I tried to do a little bit of research for this. I actually tried to watch the movie Murder by Numbers, which is where the two of them met. Okay. And this was. It was a tough watch, certainly. Yeah. Just honestly, I made it about 40 minutes.

[Joe Peacock]

I second screened this movie with you this morning. Yeah, it was so bad, I've already forgotten about it. Yes, it was a rough watch. She was kind of like her character from Miss Congeniality, but in, like a Criminal Mind.

[Chan]

Correct. It was very dark and grim gory. At one point, I asked you. I said, can we just mute this? Because I was just like, yeah, I was just trying to get through it.

[Joe Peacock]

But Ben was really into it.

[Chan]

I think Ben was interested in that, but I think he was just excited to be watching a movie in the morning. You know, I typically don't allow that in our house. Okay. So Sandra was approximately 16 years older than Ryan Gosling when she played this, you know, detective character. Really? It is her character in Miss Congeniality.

[Joe Peacock]

He looked 20 at this point. He's young.

[Chan]

He looked very young. He's very, very young.

[Joe Peacock]

I mean, he. He wasn't. But he plays a high school student.

[Chan]

He plays a high school student. Yeah. And so, you know, these two, they're spotted on the red carpet. Really? Yeah. I'll show you some pictures. It's pretty. It is cute.

[Joe Peacock]

I think they both seem like they have a really, like, cute, fun energy.

[Chan]

Yeah.

[Joe Peacock]

About each other. Yeah.

[Chan]

I was also seeing that maybe they were. They might have been Friends with benefits.

[Joe Peacock]

Okay. Yeah.

[Chan]

That also kind of, like, thought it was fun for their careers to be kind of spotted together. So there's the two of them.

[Joe Peacock]

Wow. Cuddly.

[Chan]

Cuddly.

[Joe Peacock]

Oh, my gosh.

[Chan]

I know, right?

[Joe Peacock]

Cute. She looks very happy with.

[Chan]

She does look quite happy with it.

[Joe Peacock]

Yeah.

[Chan]

But he really does look, like, so young. I mean, I feel like he's also just freshly, like, out of. Doesn't he. Isn't he from Utah?

[Joe Peacock]

He definitely grew up Mormon.

[Chan]

Yeah.

[Joe Peacock]

I believe he's from Canada, though.

[Chan]

You're right.

[Joe Peacock]

But there's, like, a famous video of him at a presumably church talent show, because he's definitely on a church stage.

[Chan]

On a church stage. Yeah.

[Joe Peacock]

Yeah. He, I think, was in the Mickey Mouse Club with it with everybody.

[Chan]

Right.

[Joe Peacock]

Russell and Brittany.

[Chan]

Okay, so I just want to also check in here and say that ryan gosling was 21 years old.

[Joe Peacock]

Okay.

[Chan]

When he began dating Sandra bullock, who was 16 years older than him. So she was 37.

[Joe Peacock]

I'm sorry. That's respectable and just a win for a woman. This is not a double standard. 21 makes all the difference from 17.

[Chan]

This is not a Rocky Parker and Patrick Dempsey situation. Like, I really think there is a. There's a significant difference between being 17 and 18 and being 21.

[Joe Peacock]

And Ryan's pretty established at this point.

[Chan]

Yes.

[Joe Peacock]

His name's on the poster. He's had success.

[Chan]

Right, right. And, yeah, they were together for about two years from 2001 to 2003. And, you know, there's really. There isn't some big, salacious tale here. In fact, Ryan Gosling has spoken really warmly about Sandra Bullock in a recent interview. Sorry, not recent recent, but right before he met Eva Mendez, he described Sandra Bullock and Rachel McAdams as the two. As two of the greatest girlfriends he'd had. And he just suggested that show business was actually to blame for all of us, that show business just naturally pulls you apart because you're wanted in a bunch of different directions. And. Yeah, like, there's not really, like, a lot more to it than that, you know? Then he goes on to date and marry Eva Mendez, and she's six years older than him, I believe.

[Joe Peacock]

This whole conversation just makes me love Ryan Gosling more in a way I didn't think was possible.

[Chan]

I know, I know.

[Joe Peacock]

I would love to see Sandra and Ryan, like, run into each other on the red carpet. Not a salacious way.

[Chan]

Totally.

[Joe Peacock]

Yeah.

[Chan]

Just like, she could say, you know, I loved Barbie.

[Joe Peacock]

I would love your thoughts on Barbie.

[Chan]

That would be huge also, because I really like the idea of Sandy, you know, having love for Ryan Gosling. And I always compare Ryan Gosling to Ryan Reynolds. Who we'll get into.

[Joe Peacock]

Yes.

[Chan]

Yeah, yeah.

[Joe Peacock]

Like Ryan. I think you always say Ryan Reynolds wishes he were Ryan Gosling.

[Chan]

Yes, yes.

[Joe Peacock]

But people don't take Ryan Reynolds seriously because we. What do I always say? If he wasn't acting, he'd be a TikTok dad. Like, that's just what he gives.

[Chan]

No, truly. No, truly. So should we just get into Ryan Reynolds?

[Joe Peacock]

Let's.

[Chan]

Okay.

[Joe Peacock]

Yeah.

[Chan]

This episode is sponsored by BetterHelp. Finding the right support can feel overwhelming. When life gets busy and complicated. Many people are looking for a practical way to talk through what is going on without adding more stress to their schedule. BetterHelp connects people with licensed therapists who have at least three years and 1,000 hours of hands on experience along with the required education, training and certifications. Getting started is straightforward. You answer a few questions, get matched based on your needs, and can switch therapists at any time if the fit is not right. More than 6 million people have used BetterHelp globally. The feedback from real users is consistent and positive with an average live therapy session rating of 4.9 out of 5 based on over 1.7 million client session reviews. You can check the Reviews [e-mail] reviews to see the daily feedback from people who have actually used the service. See the reviews, see what stands out and see if better help is right for you. Visit betterhelp.com popapologist that's better. H E L p.com popapologists okay, so getting into Ryan Reynolds. We're going to talk about Ryan and Alanis Morissette.

[Joe Peacock]

Crazy.

[Chan]

Crazy.

[Joe Peacock]

Just they do. They seem like from different worlds.

[Chan]

Different worlds. Also because he's had like Scarlett Johansson. After doing my research here, I believe he's a love addict.

[Joe Peacock]

Say more.

[Chan]

Moves on very quickly and he's kind of always in like, like he basically. I mean. Okay, let me just. I'll get into it later. Let me set up with Alanis Morissette. So Ryan Reynolds and Alanis Morissette begin dating in 2002 after they reportedly met at Drew Barrymore's birthday party.

[Joe Peacock]

No.

[Chan]

Yeah.

[Joe Peacock]

Drew's parties have linked so many people together. I was just watching the Anne Hathaway interview with her on, on the show. And Anne Hathaway's second date with her husband was at Drew Barrymore's party.

[Chan]

Of course. Of course. She's a connector.

[Joe Peacock]

She's a connector. And this is not an ad I love the Drew Barrymore show. It feels she's doing something different on daytime television than anyone else. And it feels like watching my mom get visit taught, like these women explain

[Chan]

visiting teaching for those who aren't sure.

[Joe Peacock]

Sure. Visiting teaching in the the LDS Mormon Church growing up was when women were assigned another sister to kind of shepherd and just check in.

[Chan]

Yeah. So like once a month you go over and just sit with them, talk to them, maybe share a spiritual thought.

[Joe Peacock]

I'd accompany my mom because I was like, you know, 8 years old. Of course, the sister she was visiting teaching would set out graham crackers for me, shout out Sister Herbert. And these two women would just chat and connect about life. And I watched my mom get visit taught by Sister Mickelson.

[Chan]

Yes.

[Joe Peacock]

And watching these shout, shout out to Catherine, watching these two women just cry and like go at it at 2pm in the afternoon about the deepest stuff in life. My cup was filled.

[Chan]

Yeah.

[Joe Peacock]

I felt like I had been visit taught 100%.

[Chan]

I think now it's called ministering, but I think it's a lovely part of like church culture.

[Joe Peacock]

Yeah.

[Chan]

So. But anyway, stepping back from LDS church culture and back into the Ryan Reynolds and Alanis Morissette universe.

[Joe Peacock]

I'm sorry I took us there.

[Chan]

That's okay. I'm actually so glad you did because I should probably. I feel like I should dip into Drew Barrymore's TV show because I do support her and yeah, I connect with her on a lot of different levels. So they get together in 2002 and they actually get engaged after two years. Apparently he flies to Ottawa, so they're both Canadian. He flies to Ottawa to ask her parents for permission and he flies back that very same day and proposes and chant.

[Joe Peacock]

At this point, I think Alanis Morissette is much more famous than Ryan Reynolds.

[Chan]

Yes. She's. She's already released Jagged Little Pill.

[Joe Peacock]

Ryan Reynolds has maybe been like in a Van Wilder film. I'm going to show you a photo, friends.

[Chan]

You're going to know, like, this is

[Joe Peacock]

a catch for him.

[Chan]

Yes, absolutely.

[Joe Peacock]

And she's a bit older.

[Chan]

I want to say she's three years older than him.

[Joe Peacock]

Okay.

[Chan]

She's 30 and he's 27. He. He's definitely have. He's not a little glow up. Because this photo is quite shocking.

[Joe Peacock]

This really is. He looks like a Chad who like eats chips all day.

[Chan]

Yeah.

[Joe Peacock]

Yeah. That's crazy.

[Chan]

And I think it's really the facial hair that's. That's kind of unkempt.

[Joe Peacock]

Yeah, it's really. That's this is definitely superhero Ryan Reynolds.

[Chan]

Yeah.

[Joe Peacock]

The facial hair does not do him any favors.

[Chan]

No, it certainly does not.

[Joe Peacock]

He looks slimy.

[Chan]

Yeah. I think there's, like. There's something American chopper about his.

[Joe Peacock]

Yes. Yeah.

[Chan]

But anyway, they are very much so in love, and Alanis describes him as someone, you know, she believes she could spend her life with, and she praises, like, his ability to communicate and take responsibility.

[Joe Peacock]

Sure, but what songs are you gonna write about Ryan Reynolds? Like, get out of here.

[Chan]

Well, we'll get into that.

[Joe Peacock]

Okay.

[Chan]

So, yeah, they were together for a long time, and so after getting engaged in 2004, they don't actually ever marry, and they break up at the end of 2007. So they're together for five years.

[Joe Peacock]

Is there anything more embarrassing than breaking off an engagement, marrying the wrong person? I get it. But, like, it's a close second.

[Chan]

I feel you. I feel like ending an engagement feels a lot more dramatic. It does, somehow, than a divorce. I don't know. It's kind of sad because I do think you're better off ending an engagement than getting married and getting a divorce. So I think it's. We've. So. I think we've all just kind of forgotten about this relationship. At least, you know, we have, because he goes on to then meet Scarlett Johansson very soon after and marry her.

[Joe Peacock]

Crazy.

[Chan]

Crazy.

[Joe Peacock]

So I want to know what. What went wrong between him and Alanis. And I know we may not know that, but, like, she. Imagine being engaged and.

[Chan]

I know.

[Joe Peacock]

Marry someone.

[Chan]

I know. I know.

[Joe Peacock]

Same.

[Chan]

I do kind of wonder if this was kind of.

[Joe Peacock]

She dodged a bullet.

[Chan]

She dodged a bullet for sure. But, yeah, I just wonder if his star was rising and he just kind of felt like maybe he outgrew her, even though that's crazy, but his career would go on to do so much more. You know what I'm saying?

[Joe Peacock]

Change the dynamic. Let's just say I don't think Alanis would want to be sitting around while he's doing Mint Mobile commercials.

[Chan]

No. Especially now, looking at the two of them. He's really not the guy for her. You know, that's. That's putting it gently. Like, I just. I feel like he was maybe on, like, his own type of an ascent, and it was definitely, like, gravitating away from what she was interested in.

[Joe Peacock]

Yeah.

[Chan]

Okay. So Alanis Morissette goes on Howard Stern after the breakup, and at this point, Ryan Reynolds is already dating Scarlett Johansson, and Howard Stern just, like, asks her all these ridiculous questions. He says, you know, I'd Never heard of this guy. Are there a lot of angry songs on your next album about him? And Alanis Morissette does, like, a beautiful job of being sincere and vulnerable, but also not kind of giving in to Howard Stern and trashing Ryan Reynolds. She does say, though, that she went to therapy five days a week after the relationship to just sort of, like, process and move through the emotions because it really did a number on her. He also then asked her what she thinks about Scarlett Johansson's music because. Did you know that Scarlett Johansson, like, released some music?

[Joe Peacock]

I didn't know that. I know she dated Jack Antonov, so I did not know.

[Chan]

Yeah, but he, like, tries to, like. He says, like, I've heard it, and it's terrible, and she's, like, very tactful. But anyway, yeah, apparently there's a song called I think Torched, and that song is, like, about Ryan Reynolds.

[Joe Peacock]

And what do we get from Torch? Do we find out he was unfaithful? That he broke her heart? Yeah, the other way around.

[Chan]

So I don't. I don't totally know. They actually released, like, a joint statement after this, the five years of being together, just saying that they had ended their engagement. I don't know, though. Like, she does say that she stayed in that relationship a little too long, and that was what took a toll on her. So I don't know if maybe she was the one who left. Even, like, you can still be the person who does the breaking up with and be very, like, torn up about it, you know, and still be, like, really hurt and. And, you know, going through a lot of personal turmoil. So I also kind of wonder if, like, after the Uncle Joey relationship, if the Ryan Reynolds relationship was, like, exactly what she needed, but then she just, like, stayed a little too long, and they actually weren't totally right for each other. I mean, clearly they weren't. And, you know, I mean, it's just the song about him, I don't believe is as scorching as you ought to know.

[Joe Peacock]

Okay. Which I wonder if that's allowed to be played in the lively Reynolds household.

[Chan]

Oh, surely it's not.

[Joe Peacock]

I assume it's not.

[Chan]

Also, to go back to my original thesis that Ryan Reynolds is a love addict.

[Joe Peacock]

Yes.

[Chan]

So he's with Alanis Morissette, then he's with Scarlett Johansson. He leaves Scarlett Johansson for Blake Lively. Like, has this man ever really been single?

[Joe Peacock]

Now he's in bed with Mint Mobile.

[Chan]

He's a love addict, everybody.

[Joe Peacock]

That and. Or a grifter. I just, like, I can't Help but think he was attracted to Alanis because she was, you know, had.

[Chan]

And then he just kind of like, jumps ship.

[Joe Peacock]

Right, Right.

[Chan]

To a bigger name.

[Joe Peacock]

ScarJo. Yeah. Crazy that he actually married Scarlett Johansson.

[Chan]

I know.

[Joe Peacock]

This couple just came to light in the last few months. So this is Andrew Rannells of Girls and Book of Mormon fame and Anderson Cooper of CNN fame.

[Chan]

Okay, this one blew me out of the water because we had no idea.

[Joe Peacock]

We had.

[Chan]

This is not like we forgot. We had no idea.

[Joe Peacock]

There's no photos. And what happened was Andrew Rannells was on a podcast recently, and he revealed that he said, I told Lena Dunham and Jenny Connor a story about when I was 25 that I had dated Anderson Cooper, and I told them about the experience and what that was like. He explained, we had a very brief relationship, but when I told them that, they were like, oh, that's a fun story. So then they used it. And that was Elijah's whole arc where he was dating that much more successful gentleman who was a bit older than him in Girls.

[Chan]

Yes.

[Joe Peacock]

And Anderson is 12 years older than Rannells, and they. They met when Anderson Cooper was 37 and Andrew was 25. But what's funny is Cooper was asked about this because there were whispers that that character was inspired by Anderson Cooper. And Cooper is a fan of the show. And when he was asked if the character of Elijah's older, successful boyfriend was. Was based on him, who replied, I just met Lena Dunham at Sundance, and she didn't mention anything to me, but I'd be flattered. Wait, is that the guy Andrew Rannells is dating? I thought he was a more of a Bill O'Reilly character. I'm a friend of Andrew's. I should ask him.

[Chan]

Oh, interesting.

[Joe Peacock]

I know. I just feel like that would be pretty cringey to, like, read if I were Andrew, to be like, yeah, that person doesn't seem anything like Bill O'Reilly.

[Chan]

Right, right.

[Joe Peacock]

And also a friend. I mean, what is he supposed to say?

[Chan]

But also, yeah, that is like, playing dumb to the extreme.

[Joe Peacock]

Yeah. Yeah.

[Chan]

Wow. Yeah, I know. I feel like there's just, like, other gay relationships that we don't know about.

[Joe Peacock]

Like, I want totally.

[Chan]

I want to know, who was andy Cohen dating 10 years ago? You know, like, why don't we know more?

[Joe Peacock]

Very happy for Andy Cohen's new boyfriend,

[Chan]

and so happy about that.

[Joe Peacock]

Yeah. I think I've read both daddy diary books. They're a great time.

[Chan]

We love Andy.

[Joe Peacock]

Love you, Andy. Okay, are you ready for this last relationship?

[Chan]

Yes, I'm ready.

[Joe Peacock]

This is also one that's crazy that we forgot because they were so public and together for so long. Cameron Diaz and Justin Timberlake.

[Chan]

Okay, yeah. Did not know about this one. And when was it? Was it pre Britney? Post Britney?

[Joe Peacock]

It was post Britney and just a year after his breakup with Britney. So this is right after Justified and in between future sex slash love sounds.

[Chan]

Yeah.

[Joe Peacock]

Cameron was 34. Justin was 25. So about a decade apart. Wow. And legend has it Chan that they met at the Nickelodeon's Kid Choice Awards. Of course, when Cameron presented Justin with the award for Are youe Ready For It? Best Burp.

[Chan]

Oh God.

[Joe Peacock]

Which is award that Cameron herself had won.

[Chan]

So I've actually been the Kid Choice Teen whatever. Nickelodeon. The one where they like put the on you as a child.

[Joe Peacock]

Yeah.

[Chan]

No, as an adult actually.

[Joe Peacock]

Say more.

[Chan]

My. My best friend Tara, she was a part of like some type of UCLA

[Joe Peacock]

student body something and ucla great sponsor.

[Chan]

I think they had it. They were. They were having it at ucla. So I got to go. But yeah, that's the one where they throw the slime on you.

[Joe Peacock]

Totally. Yeah.

[Chan]

Anyway, so I've been. This is a great moment for romance. I understand the scene. Wow. Best burp.

[Joe Peacock]

Best burp.

[Chan]

That's disgusting.

[Joe Peacock]

Truly. But Cameron herself had won it. They were together for three to five years. And you'll notice when looking at their photos that it wasn't far from the Britney era because there's also some cringe outfits. Just this early 2000s fashion.

[Chan]

These two style icons.

[Joe Peacock]

Matching jerseys. She's so cute and like so cute. I'm happy for her with this relationship. Like that must have been a fun time.

[Chan]

Yeah, yeah.

[Joe Peacock]

But also like dodged a major bullet.

[Chan]

No beyond.

[Joe Peacock]

She looked very in love and I'm sorry, but I can't help but think that like he has demons and he's with this angel. I know, I know. Yeah.

[Chan]

And I mean I just feel like he doesn't number on all the women that he's with.

[Joe Peacock]

He really does. I hope that she got out relatively unscathed because after they. They broke up like maybe five years later she did bad teacher with him. And as I understand, you know, like I'm pretty sure she's producing that movie. She's the star of it and she wanted Justin for that role. And like they share I guess like a very awkward sex scene in that.

[Chan]

No way. So they had dated when that like. Oh my gosh.

[Joe Peacock]

I know, I know.

[Chan]

So I guess, yeah, things must have not been on that bad of terms

[Joe Peacock]

no, except they did kind of end very tensely. Are you ready for this?

[Chan]

Yeah.

[Joe Peacock]

So they were together for three and a half years, and Cameron introduced Justin as the musical guest on SNL in December. Okay, okay. By the next month they had split and he was dating Jessica Biel by the next month. We'd eventually marry. Well at the.

[Chan]

And cheat on and.

[Joe Peacock]

Oh yeah, I saw those photos. Wasn't surprised. Okay, so the month after they've broken up, he's dating Jessica at Princess Golden Globes after party, according to multiple witnesses. This was in the Post. This was in People. Timberlake was chatting with actress Jessica Biel when Diaz approached Beale, stepped away, and the former couple had a serious exchange. Diaz walked away, Timberlake followed, and the two were soon spotted and engaged in an intense 40 minute face off in a side room.

[Chan]

Oh, I. Wow.

[Joe Peacock]

Right? Diaz reemerged looking composed, but not before Timberlake held his head in his hands and says a witness slammed his fist down in a cabinet. But insane slammed is.

[Chan]

Oh my God.

[Joe Peacock]

I know. And, and like the, the gall and confidence, which I love for Karen to walk up to Justin and Jessica chatting.

[Chan]

Yeah.

[Joe Peacock]

Like I would do the same. Like this is a month later.

[Chan]

Right, right.

[Joe Peacock]

I feel like an episode of Girls that this happened in as well also.

[Chan]

It's so Justin Timber. Like, I feel like to like punch something. The guy who wins best burp is also the guy who punches a wall.

[Joe Peacock]

I couldn't have said it better myself. Amen then. It's funny because just months later, contractually, they're forced to be on a red carpet together for what? Shrek the Third. Oh, gosh, I think Cameron got him voice work in that movie. And there's a photo of them just smiling together on the Shrek the third red carpet.

[Chan]

He's got that shit eating grin like always.

[Joe Peacock]

100%.

[Chan]

Wow.

[Joe Peacock]

Time is the biggest healer of all though, because again, they did Bad Teacher together and I guess so. I like to believe she is very happy with one of the Madden twins.

[Chan]

Yeah, no, I. I believe she is, Jo. I love that sentiment. The time is the biggest healer because I feel personally like it will. It will just take a little bit of time for me to heal from these relationships that we've uncovered. You know, like from the Patrick Dempsey and Rocky Parker relationship. From the. I mean, I will never look at Jerry Seinfeld the same again.

[Joe Peacock]

No. And I'll never look at Patrick the same again. Yeah, yeah, yeah. These were some dark places, but also some, some bright places. Jake and, and Reese.

[Chan]

Jake and Reese. You know we have texture there now, thank God. And you and I are going to blast all too well the entire way home from this recording so that we can just kind of like get back to homeostasis.

[Joe Peacock]

I need that because those photos of Jake Gyllenhaal walking Reese's Kids like that did a number on me.

[Chan]

Yeah, it's, it's, it's hurting our testimonies. So, everybody, we've got our work cut out for us to kind of go unlearn some of what we've just shared. Thank you so much for listening. Joe, thank you for coming on the podcast. We love you. You are the best and we can't wait to have you back.

[Joe Peacock]

I loved being here. Thank you, fam.

[Chan]

Bye.

[Joe Peacock]

Hello and welcome to Pluto Foe. If you know the name of the movie you'd like to see, just stream it for free on Pluto tv where all your blockbuster favorites are landing all summer long. Catch. Anchorman. The Legend of Ron Burgundy. Fantastic. The Matrix Trilogy. Welcome to the real world, mean girls.

[Chan]

Shut up.

[Joe Peacock]

Titanic.

[Chan]

I'm the king in a world.

[Joe Peacock]

And so much more. For Showtime's press, nothing. They're free 24.

[Chan]

7. That is so effective on Pluto TV.

[Joe Peacock]

Stream now. Pay Never. I'm Justin Sylvester. And I'm Blakely Thornton. Join us for yesterday, the podcast where we break down the most pivotal pop culture moments in history and give them the queer love that they deserve. The things that got us riled up during dial up, those makeouts that should have been breakouts and the drops that were cemented in pop. I'm talking Benifer, Tyra versus Naomi, Tom Cruise jumping on that couch and so much more. So please rate us, subscribe to us on Apple podcast, Spotify or anywhere you get audio related content. We also take Venmo and Cash app ach or credit card number as well. We're malleable, you know we're gay today.

[Chan]

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[Joe Peacock]

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[Chan]

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[Joe Peacock]

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