The Press Box - Ep. 84: 'Jam Session' With Juliet Litman and Amanda Dobbins

Episode Date: April 6, 2016

Juliet and Amanda go through the archives of celebrity dating triumphs and tribulations to select the best relationship runs. Then, they play Two Truths and a Lie to see how well they know celebrity dating history. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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which is just two taps on your phones. You can buy or sell tickets. If you're making your first purchase, use the code BSPN to get $20 off. Don't forget, BSPN. you see geek it's a great way to buy and sell tickets welcome to jam session i'm juliette letman i'm amanda daubbins this music just like freaks me out for some reason i've started doing a dance kind of like the car wash uh dancer dudes you know that wave in the wind oh yeah like one of those like we should get a we should get a mascot jam session blow up doll just to hang out here while we

that's a great idea um today we're talking about celebrity couples because we're a little sad that Drew Barrymore and her husband Will Cappellman are divorcing. We are sad about that. On the flip side, we're very happy about developments in Wendy Dang's life, potential developments. So we're going to start sad and then move on to really inspirational news. This podcast follows the age-old adage, never end a podcast with sadness. So we'll be going from sad to happy. Drew Barrymore and Will Capplman.

Do you like Drew Barrymore? I love Drew Barrymore. Interesting. What's your favorite Drew Barrymore movie? Or just like, what's your favorite piece of Drew Barrymore media? full stop oh interesting you know never been kissed is very important it's there for me um i just kind of like her friendship with adam sandler i think it's very strange true but for some reason i find it very endearing and like they were on jimmy fallon together like a year or two ago or whenever they had a

horrible movie come out was that blended blended was two years ago and it was desperately bad it was just unforgivably bad and racist i think i didn't see it i did somehow i thought it was going to be like a great reunion of Drew Barrymore and Adam Sandler and no. You're so dutiful about going to the movies. Let's blame him for that disaster, and not her. I do. She had great outfits, like, definitely made well cast her whole movie, and it looked wonderful.

I remember they were on Fallon together. They played a game. It was just, like, cute. I feel like she's a good friend. She also set out Jimmy Fallon and his wife. I was going to say that the thing I like about Drew Barrymore is really just good vibes. Yeah. And every interview that she gives, she is kind of interesting and present sounds too hippie-dippy, though I do feel with Drew Barrymore.

Like, hippie-dippy is not like the wrong way to talk about her. No. But, you know, she's clearly fun. She clearly is engaged and is like trying to talk to every person that she wants to talk to. And there's a person behind the eyes. Yeah. I mean, she was a wild child star and she made it through the other side. Now she's like a fun adult celebrity.

Great stories. Yeah. She's lived a lot of lives, which is really interesting. I know. feel like she's I thought she had settled into a good place, but some of these quotes coming out about her divorce are just making me really sad. I'm going to read them. This is the official statement from her and Will Cappellman.

Sadly, our family is separating legally, although we do not feel this takes away from us being a family. Divorce might make one feel like a failure. That's just terrible. But eventually, you start to find grace in the idea that life goes on. Our children are our universe. We look forward to living the rest of our lives with them as the first priority. This is very sad.

So this makes me sad on a couple levels. Okay, break you down. So, and I want to... Level one. Okay, well, let's first talk a little bit about celebrity couples and how we get invested in them. Love it. Because there are two, there are kind of two avenues in which I get attached to celebrity couples. One is through just like randomness and it's like two weird people who have probably found each other and it makes no sense.

And you're just like, what do they talk about all day? That's the couple that found love in a hopeless place. Exactly. And we're going to talk about a lot of those. But this one is, I'm just really, I feel for Drew Barrymore. Yeah. And I just want Drew Barrett. So I don't, like, Will Coppulman, like, seems nice.

And to the, I was interested in him to the extent that he could make Drew Barry more happy. There was some real shade being thrown on him on page six. It's a quote, Kaufman always wanted things his way. They're complete opposites. She's more of a free spirit and he's more buttoned up. She's also more successful. No one ever really knew what he did. Yeah.

Zing! Wow. I mean, that's definitely a Drew, Drew Camp. Yes. But I, so he's, yeah, like we're like going to say goodbye to him. I feel like they're the type of celebrity couple where she goes for like normal guy because she's sick of like celebrity world hoping like this is like salvation going for someone regular. And then it turns out that like regular guy I can't handle celebrity life. And also just a little bit deeper than that, which makes me very sad. You know, Drew Barrymore did not have a traditional family existence in any way. Like she was just hanging out with her babysitter and doing substances at an early age. and like doesn't really speak with her parents anymore. And so you can, I just wanted to have a family. I know, and they talk about this in all the pieces. Like, Drew Barrymore really wanted to have a family.

And you can see her, like, trying for this traditional structure and a husband and kids and, like, the nuclear thing that she didn't have. And it didn't work out. And it's really sad. Yeah. And maybe not surprising, you know, it's hard to merge families and family structures. You get kind of used to what you're used to. Right. But it's sad because, you know, I really feel that she wanted it.

I know, it seems like she really did. her husband's Jewish and like when they got married and she was pregnant she's like yeah I'm going to raise my daughter and the Jewish faith thinking about converting she was like all in on this new family and so her husband um he's the brother of Jill Cargman of odd I didn't know that brother or brother and not no I think I think brother because she and Jill Cargman became good friends and like Jill Cargman did her she was recently on the cover of Vanity Fair no not Vanity Fair Marie Claire and um Jill Cargman interviewed her for the cover of Marie Claire so she really went all in on the family. Oh, that's just so upsetting then. Really, really tough. Yeah. I also thought that in this

note, or there are statement, although she said, our family is separating legally. Like, thank you for indicating it's a legal separation. I feel like Goop and Chris Martin really, like, messes up for everyone that, like, now a divorce statement has to, like, clarify between, like, legal and spiritual. And like, like, we get it. A divorce is a legal transaction. Like, thanks for reminding us, but like that's clear. It's actually only like it's weird to for it to not be legal. Catterpoint. Okay. I feel like Goop has started, listen, the conscious uncoupling thing, I'll never forget when I got that email. I'll never forget when I got that email. I was working in New York magazine. I was in the office. I just started screaming. My friend, Noreen Malone, who's also a

goop fan, walked by. I just pulled her over. Did you guys cry? Well, we started screaming without communicating to anyone else in the newsroom what was happening. And so they thought like some sort of like seismic world event had happened. And then I just finally managed to gasp out like, check your goop. Check your goop. And then everyone read the email about conscious uncoupling. So everyone made a lot of fun of that with good reason, ridiculous name. I do think that they've started sort of again, like possibly too emotional, but a constructive trend about like talking through a break up in therapeutic terms. Like people go through a lot.

It's like therapy going mainstream. Exactly. And they're helping other people like work through the process of breaking up and giving them new language and ways to know they're not alone. It's like it's sad and gross and maybe too much, but maybe it's helping people. Sure. Sure. Maybe it is.

Or at least it's helping Drew Barrymore. I mean, I feel like also their kids are three and one. And that's really young for for it's, I mean, maybe it's, I mean, I don't know if it's, it's like better or worse to the kids. But I feel like as a mom, like that's tough. It's hard to like share responsibility of parenting with a baby, I think. Yeah, it's also like the wheels came off real fast. Yeah, really fast.

I'll only been together for four years. Just really upsetting. And then page six is like so clearly on Team Drew here. Although I guess I guess in a celebrity couple where only one half is truly a celebrity, you pick that the star side. Because then they added she looked sad and was upset. According to our source, who added Drew was still so nice. And she was wearing jeans.

This is from over the weekend. She was wearing jeans and looked like she hadn't showered. Hadn't showered? Okay. Like, maybe that's just like what she looks like. It's unnecessary. Yeah, totally. I mean, I'm sure I often look like I haven't showered. She was later whisked away in an Uber.

I like that it's an Uber, not like some fancy car service. And then on Saturday, she was seen promoting her own line of wines at the Pebble Beach Food and Wine Festival. Meanwhile, another source told us the breakup. There was no cheating involved. Drew gave that relationship everything. She's all about family. She would do anything to maintain and fight for because she wanted a husband and kid so badly. she did everything for that. So no question. Page 6 is Team Drew here. Yeah,

she has wine to make her feel better. That's true. It's another thing I like about her. She's another celebrity who openly indulges in booths. The liquor business is just like has exploded with celebrity intervention in the last like 10 years. Like I feel like Puff Daddy was actually like early to this with like him being involved with Surrock. Sure. And it's just and then like there was the whole entourage plot line about the tequila. And now everyone has like some kind of liquor or wine or something. I drove by a sign this weekend that was to like Casamigos ranch. Oh yeah. And I just like started screaming. I was like, Casamigos, Casamigos. And no one in the car knew that what I was talking about. If you don't know, that is George Clooney and Radie Gerber's

tequila. Yeah. Did you go? No, I didn't go. Another time I did see like a Casamigos truck just like parked in Brooklyn. And their faces are definitely plastered on the side of the truck, which I thought was an unusual decision for George Clooney. And I've never seen their faces in the their branding before. How surprising. I just didn't know that the barrier to entry of the liquor business was so low, and then apparently the profits were so high. Like, everyone's doing it, so it must be like some cool thing. I can't get over it. I'm sad for Drew Barrymore, but I hope she finds love again. And I think she might, based on the other people she's dated. Great segue. Let's look at her long list of dating history. So we were going through this. I did

not put them in order. But let's just note the first of all, she was married before, to a man named Jeremy Thomas, whose name I did not know before today. Did you? No. People magazine did like a cover story about her getting married in 1994. Wow. On the cover, it said, Drew Barrymore lands on her feet at 19 with a nifty Welsh groom. Thank you. So first of all, who are they thanking? Like, who is that thank you directed at? Like, is it thank you to God? Like, is it thank you to the universe? Is it a thank you to Drew? Like, I don't understand. Thank you to the people of Wales. Like, are they trying to, like, mimic the way a Welshman would talk?

Yeah, I'm not. Lends on her feet, thank you. Like, I would try to do a Welsh accent, but I can't. It's good choice. So I just won't. So that was at 19. I mean, I don't think most people get married at 19 could really have it last. But I don't even know.

So his name was Jeremy Thomas, which is, like, as British of a name as there ever will be. And, you know, she's just been looking for this for so long. Yeah, she was also married to Tom Green, right? Yeah, they were married. Were they married? They were married, yeah. Oh, my God. I was going to say it's kind of amazing that she hasn't married anyone else.

Yeah. Tom Green, surprise. My favorite at Drew Barrymore X is still definitely Fat Moretti of the strokes. And I vividly remember some, she was on David Letterman kind of when they were dating and when the strokes were still a thing and was talking at length about just like hanging out with the strokes and being an awesome strokes groupie. And I was quite jealous. Really would have liked to be part of that with Drew Barrymore and Fatmready and Julia.

And Julian. When I was in high school, the strokes came, like, last night came out when I was in ninth grade. And everyone knew so. Everyone, and I went to a New York City public school for high school. And everyone had a connection to the strokes. Everyone's like, oh, because they went to lab. And everyone's like, oh, I know them. Or like, so-and-so knows them.

And everyone's, like, trying to, like, claim ownership over the strokes. And they just got, like, way more famous than anything anyone ever would have guessed. They really blew up. Because one of them also dated Kristen Whig, right? I was about to say, can I say my favorite, random celebrity couple of all time might be fan ready and Kristen Wick. There was like a brief, glorious three weeks where they were just all over each other at random clubs according to the page six and the Daily News. Yeah, it's amazing. What are like what are the strokes up to right now?

I can't remember whether they're still under contract to do another album. They're just like they're just like such New York City kids. Yeah. Like I just feel like everyone who grew up in New York like wants to adopt them as part of their own lore. Julian wrote some songs for vinyl. Oh, that's Cool. And he's making weird music. That's nice. I wish he would just make more normal strokes music, but whatever. I'm trying to figure out what Jeremy Thomas is up to now.

And there's just no information about him. There's a British director named Jeremy Thomas who's like hogging all the Google results. But he was a bar owner at the time, just so you know. So that really speaks to where Drew was at when she was 19. Honestly, as a 19-year-old marrying like a Welsh bar owner. It's pretty cool. That's living the dream. That's like the study abroad dream.

It's true. go abroad to Dublin, Edinburgh, and just like find a local and you stay. I feel like we can just call this Drew's study abroad period. Like maybe there are some legal arrangements that facilitated it. And that's fine and good. All right. Should we talk about the other? She really had to run.

Yeah. We just kind of breeze past Tom Green, but like that's so weird. That was definitely a moment in Drew's life in early 2000s moment. That was just really, that's like kind of marrying Sasha Baron Cohen. Yes. But like without the genius behind it. Like, I don't know. I just don't think Tom Green like, you know, necessarily has the same brain power, but like what went for very similar stunts.

True. It's so weird that he was, like, famous. It's just bizarre. He's like an internet star before the internet was, like, a big thing. Like, I feel like if he had come, like, 10 years later, maybe we'd still be talking about him. Or he'd have a podcast. That's what he'd be doing. He would be, like, podcasting from his garage or something about, like, his past fame and whatever.

He should do that now. What's holding him back? I don't know. All right. I've had an idea for your time, Green. Okay. Moving on. Corey Feldman, of course.

Yeah, sure. Had to be involved with the Corey if you were a star in the 80s. And David Arquette, like some really early good, late, early 90s stuff happening there. Oh, yeah. He's essential to that time period. And then probably one of the most important figures in the celebrity dating canon, Justin Long. That went on for a long time. It really did.

No pun intended. Sorry. All right, so should we use, so that's Drew Barrymore, pretty good dating streak. Not a, not a plus level. No. But there are a lot of important, there are a lot of bold names on that list. Justin Long brings a lot of people together. Justin Long brings a lot of people together, which is I think we're going to now segue into celebrity dating streaks. Let's do that, but first, let's talk about our sponsors. TV has never been better, but it's also never been more expensive. With all the contracts and

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Simplysafe33.com. All right. Let's get back to these celebrities in their dating lives. So Justin Long, he's kind of the Bermuda Triangle of many young female stars. His dating resume is pretty impressive. And we're going to, in this segment, rely heavily on who's dated who. Anything you want to say about that website, Amanda, as a disclaimer? Okay, I don't think who's dated who is 100. I think they have collected kind of some true celebrity tabloid reports and some less true celebrity tabloid reports because I hope you guys all know that there is like a hierarchy within celebrity tabloids. There is. Can you break it down?

Sure. People Magazine and Us Weekly are tried in true sources. You can trust them. They're vetting things. Except that they take a lot of stories about The Bachelor and the Kardashians. Yeah, that's true. And they steal tweets. I mean, you know.

It's a different, competing of the internet has changed things for them. That's true. Also, I think that we should, people is the only one that's 100% right. Yeah. Because people come straight from the publicists. From the publicists. Us Weekly does its best and you can usually trust it. But, you know, obviously, let's, you know, be smart.

Be smart. Always check your sources. TMZ. They're really good. They're really good. Yeah. And then after that, I don't know, you got to be skeptical. I think that the National Enquirer is underrated for their veracity.

It's true. However, they're also scumbags that, like, supported the Obama birther's movement. But they've broken a lot of big stories. It's true. Especially when it comes to politicians. John Edwards, Monica Lewinsky, O.J. Simpson. Oh, yeah. Now they're going after Ted Cruz, which I'm inclined to believe.

Wow. All right. Okay. This took a turn. I just want to say that they may be scumbags, but National Enquirer often correct. That's very true. I just sort of, they seldom engage. and the level of story that you and I are interested in.

Yeah, there's so much dirtier. Right. There's so much, so much more reprehensible. They're like what TMZ was before the internet, too. Yes. And they just, and also like being associated with Raider online turned their brand. Yeah, radar is one that you should be skeptical of. So who's dated at who.com, also slightly skeptical.

Also sort of similar to one of my favorite website, celebrity networth.com. Oh, sure. It's like a ballpark figures on there. And Celebrity Heights.com. Yeah, that one's awesome. But, you know, we're going to use this as kind of like a baseline for jumping into some of these great dating runs because some of these celebrities, they've accomplished a lot in their personal lives. Exactly. So we would say Drew Barrymore is sort of a bee.

Yeah, she's a bee. So Justin Long has got on his resume, Amanda Safeord, Kirsten Dunst, Drew Barrymore, Maggie Kew and Caitlin Doubleday. This is, like, sneaking impressive. He did the, the other thing is that he, his longevity with these people. It's not just like they were spotted out on a date together. Like, he was with Amanda Safe Reed for a long time. He had like two years, right? I think he was with Drew for a while.

Yeah, after they were in that movie, that rom-com, which I actually kind of liked. Okay, well. Where he's like, it's like a long-distance relationship. Okay. Caitlin Doubleday also, do you watch? I'm not familiar with Caitlin Doubleday. Can you share? Yeah, she's on some cable shows, and I believe she's now on Empire.

Okay. She plays Andre, the oldest brother's wife. Oh, interesting. Rhonda. Yeah, and her sister is on Mr. Robot. So it's the come-up for the double days. So this is kind of like Justin Long was there first. Wow. Justin Long tastemaker. I'm going to give him credit for that. Because that's a good one. And also she's really pretty. She also kind of plays like a crazy woman on Empire, which I sort of enjoy. Another thing that I'd like to say about Justin Long, he's a really delightful interview. Is he? Have you met him? I have not actually, but I just remember he gave an hour-long interview about romantic comedy. to Vulture while I was there that I really recommend everyone. I think Patty Greco did it. I'll check that out.

Very good. He's very knowledgeable about romantic comedies. And I think any man who takes a romantic comedy seriously is a friend of mine. Absolutely. He's in one of my like sneaky favorites. He's just not that into you. Oh, yes. Is that even a comedy?

Do you want to share why you love he's not that into you? You want to just do like a quick 30 seconds? I cry almost every single time. Five seconds. When Ben Halfleck and Jennifer. Aniston get together at the end. I'm just so happy. It's so sweet. And like Kevin Connolly finding Drew Barrymore,

the real sadness of the movie is Jennifer Connolly, Bradley Cooper, and Scarlett Johansson. Kate's nodding his head. It's really upsetting. But other than that, there's some really beautiful storylines in that movie. Okay. That's who I wish Ben Affle really was, the guy on the boat with Jennifer Aniston. Okay.

But he's not. Dare to Dream. Yeah, I know. He's just not that guy. Anyway, back to Justin Long. So he's kind of the nexus because Amanda Safreed. We just need, Chris Ryan brought this to our attention. And her run is incredible.

Let's just read off some of these names. Okay, go for it. Thomas Adoski. Yes. Current Bo. I really enjoy it. That really passes just like the random test. Yes.

And he's from the newsroom. In case you're not like a huge newsroom had like we are. Desmond Harrington, do you know who that is? No. He was on Dexter. That's another really random one. Josh Hartnett, James Franco, Ryan Philippi, Dominic Cooper. Oh God, Dominic Cooper broke her heart.

Yes, so they met on Mama Mia. Yes. And we're each other for like two or three years. Yes, they did for a long time. And she gave some sad interviews about how he broke her heart. And also she can only eat spinach and seeds. It was a dark time. Because of him?

No, I think they were not related. She was like trying to give some like Hollywood body like real talk. Oh, no. She was like, I only eat spinach and seeds. I believe that. to me. I think that's true. However, she's also like a petite person, like, which... Yeah, I mean, you know, genetics plays a role in all of this, but also spinach and seeds. Terrible. Like, chia seeds? Like, what kind of seeds?

She didn't specify it. Wide variance and, like, what the best kind of seeds are. Um, she, like, she's gone for, like, a very generic. It's a certain genre of TV star. Justin Long might be the biggest celebrity in this for a bunch. I want to quote Chris Ryan on this, which is that, like, her list. is sort of the study of the decline of the American male movie star, which is a very good point. It's really true. Who do you think, I mean, I guess James Franco is the most famous from her list. But she'd also go Ryan Philippi for a minute, post-Rice.

Yeah, that was a tough time. Again, I think, I think I sort of got the impression that she's been pretty public about how her boyfriends are that nice to her. I bet you say, does she have good judgment in men? I'm not sure here. Well, I think she and Justin Long were together for so long because he was nice, and they posted a lot of pictures of their dog. on Instagram, I seem to recall.

She's very into dogs. She tweets about animals a lot, actually. Yeah. Like in general. I follow her. She's recently tweeting about some kind of beached whale situation. Okay. Another thing that I think it also makes me like her.

This is friendship. This is platonic, but she and Aaron Paul played opposite each other on Big Love. And they also, and then they were like, they filmed some movie together that I think didn't come out because it was really bad. But they were like really excited to be working together again, which I just thought was cute. I just like when those kinds of friendships transcend a project. I would agree.

Which speaks well of both of them. All right. So Amanda Seyfried, what rating are you giving her? I'm going to give her a B plus. Okay. Because there's not enough star power to go to the top level, but just some impressive pulls. Okay, great. I like it.

Another ex-girlfriend of Justin Long's, Kirsten Dunst. This is a pretty good one. Do you like Dunst? I love Dunst. Have you always? Yeah, you know, I'm a big fan of the Sophia movies, so I have a soft spot for KERN. That's Koppola for all you out there. Sorry. Sorry. We're on a first same basis. And, you know, Kirsten Nutz has like a great, like she doesn't care and like an

aura of just not caring, which I really appreciate. She was so good in Fargo that I just truly appreciate her. And it was not like a flattering performance, like, but she was so, so good that I hope it like steers her career in a good direction and bring it on an all-time great cable movie. All-time great. Yeah. All-time great teenage movie. Sure. I remember seeing it in theaters. It was like, I remember my parents, like, were reluctant to let me go by myself because it was pretty young. And I really loved it. Yeah. It was great. All right. So her list is quite impressive. Let's run through it. Current boyfriend, Garrett Headland. Or they're engaged, actually. I didn't know that. I didn't either. Congratulations to them. I know. That's great. It's great. Yeah. I feel like that they seem right for each other. I can get behind that. She also has on here, Fab Moretti, another one who. Really? So that's one that you don't quite, you don't believe? I feel like maybe they were just at a party together and like both having a nice time

and then someone just uploaded that. Someone just took a picture. I would love for that to be true, but I'm just kind of like that seems like a circumstantial. Hard for you to believe that one. She's also got Josh Hartnett, Jake Gyllenhaal, and Toby McGuire, which feels like a trifect of some kind. Again, did the Toby McGuire thing really happen?

Is it just because of Spider-Man? Yeah, this is what I'm saying. You know, we need to really, hold on, I'm just Googling. Toby Moore. Oh, apparently it did. Okay. All right. Amanda's wrong.

I'm sorry who dated who. Plus one for who's dated who. Okay. All right. Okay. That's great. This doesn't bode well for the game. We're going to play at the end of.

Two truths did a lie. This is going to be a good one. Her and Toby McGuire is another one where it was just like, clearly that's not going to last, but you make it work for your movie. I can't really imagine what it's like for part of your job to be like in a fake romance. Like I think that I would get very confused by that and would date all. of my like all the people that I was playing opposite it's true like I just can't imagine what that's like we're just like I'm gonna pretend to love you I feel like they probably don't pretend that much

I think you're right that it gets a little confused yeah like and then but then if you're like married to kirsten dunst or whatever and she's like yeah I'm in this passionate love affair on screen with toby McGuire whatever like how are you okay with that if you're married if you're dating kirsten don't know like I would never date an actor I'd be like okay you can be you can I'll date you if you are only in movies with other men that you're not attracted to. Like, no women in your movies, please. Like, I just, it just seems really hard. But then it's tough because, like, I wouldn't want to see any of those movies of, like, a dude just

in a movie with all other dudes and I don't care. So you'd be dooming their career. Right. And then, but also, I just think it would be, like, it would not be a supportive relationship because I wouldn't care about his work at all. And then, you know, wow, you can't win. Like, George Clooney, since meeting a mall Clooney has not had many, like, romantic roles or really a lot of acting roles, period.

And, like, I feel like that bodes well for their marriage because there's nothing to, like, distract him from his great, I'm assuming great wife. Okay. Yeah. I buy it. Just a theory. And, like, maybe that was Ben Affleck's problem. Too many movies.

Maybe. Maybe that was the problem. Blake lively, who's really hot. Okay. All right. Back to, uh, Kirsten Dunst dating history. Kirsten Dunst. She also, Jake Jillon Hall.

Oh, the Jake Jum. I like him. Their romance was like a great young. Hollywood romance. There's an iconic picture of her eating salad at lunch with Jake Jillen Hall outside, which is just really my mood a lot. Let's give her a grade. And then I want to get into Jake Jillen Halls because it's also really good. Okay. I think she's also like a B.B. Plus. Yeah. It's good. But again, like these these gals who have a lot of like medium stars, they don't have the big star power. Exactly. No one at like their peak moment. Yeah. Exactly.

But Jake Gyllenhaal, he's got some good ones. Right to run. Currently dating Ruth Wilson of The Affair, which is one of my favorite shows, which I'm like no longer embarrassed to admit. Are they still dating? I think so. I mean, you know, I remember the rumors like six months ago or maybe even like even longer, but I haven't seen any evidence recently.

All right. Well, maybe they broke up. Okay. Shout out to them for keeping a secret if they did. It's true. I appreciate that. Rachel McAdams for Short Dalliance is on here. Oh yeah.

But like, again, is that when they were in the boxing movie together? I think so. I think it was It was... Rachel McAdams does tend to step out with her co-stars, which I admire. Big time. Yeah, because she has some quite handsome co-stars. But, all right, keep going. Thank you, Kelly.

Oh, yeah. When was that? I believe it was like, it was after Derek Jeter. Oh, okay. So, yeah, it was like a few years ago. Hard to call it Derek Jeter. Congratulations, Jake Gyllenhaal. Taylor Swift, obviously.

Right, maple lattes. Yeah, we all recall that. We inspired the best Taylor Swift album, in my opinion. It was a good one. Yeah, I mean like... The song's about him. Again, he's all too well, which is my favorite Taylor Swift song. After you mentioned how much you liked that one, I went back and listened to it, and it's really good.

It's really emotional. You can also listen to it like ten times in a row. You call me up again just to break me like a promise. Wow. Jake Gyllenhaal, how dare you? 60 seconds on Taylor Swift. Yes. I really, Tate had me watch the Jump Man Apple video yesterday, and I really liked it.

I did too. It's hard to allow yourself to fall off. a treadmill if you're like a celebrity. I mean, the treadmill part was a little forced, but, you know. It was funny. The thing that was the most forced to me was her sports bra. It was like a fashion sports bra. It didn't have a lot of utility.

It's true. She was doing the leisure part of that leisure. Yeah, exactly. Not the athletic part. All right, anyway, but I liked that. We defend Taylor on that one. Sean Fennessee is going to burst in here like the Kool-Aid man and like cut our heads off. You know, when someone does a good thing, you need to recognize it.

Sure. I support it. But he also had Natalie Portman for a short time. I shouldn't say had dated. It's very retrograde of me. And Reese Bother Spoon. And Jenny Lewis is also on here, which I'm not sure I believe. Jenny Lewis, there's photographic evidence on all loves.

This is the thing. I want photo evidence of these people. And I have photo evidence of Jenny Lewis, Reese, Taylor, Kirsten. Jenny Lewis is probably his coolest girlfriend. Totally. That's impressive. He started cool and kind of. Then Hollywood took over.

But, you know, it's a pretty good run. Yeah. I think that's like an A-minus. Okay. I would agree. Taylor Swift just shoots you up a different stratosphere. It's true. The whole record.

Yeah, though I think he maybe got a little played there, but. It's true. I mean, I'm happy for him, I guess. Good job, Jake. Moving on from Jake. Who's next? I want to submit Serena Williams. Ooh, okay.

Give me her highlights. So this is just like a really good diversified portfolio. I feel like we've been talking a lot about actors and actresses and people like co-stars etc. All right. So Serena, you got Common. Nice. That's a great one. You got Drake. If you're dating Common, what do you call him? Like, Common or Lonnie?

Probably Lonnie. I don't know. What do you think? It's just not a cool name unlike Common's a cool name. Yeah, I don't know. And like, what does Beyonce call Jay Z? I've always wondered. Oh. Like probably just Jay or Sean? I would say, oh, but Sean's weird. I know. Like for us, it's so strange.

Yeah, I don't know. And like does Scooter Braun's wife call him Scooter or Scott? I hope she calls him Scooter. Scoots. Scoots. I don't know. It's just the kind of thing I wonder about. Common, Drake, the evil tennis guy that she fought over with Maria Sharapova. Oh, yes.

And then a Reddit co-founder, which I think is just like... That's the best one. Yeah. Alexis O'Hanian. Yes. That's amazing. I just really like, I like that she's moving around in the world. She's got a lot of interests.

She's trying on like a lot of different people who can bring different things to the table. I really appreciate that. It is really good. Also, she got the famous Brett Ratner phase. Okay. Yeah. That's...

I know you're glossing over the negatives. Well, so then I was going to bring up a kind of like a different definition of greatest, which would be January Jones. Oh, interesting. This one is really sort of like all time in its like mistakes. Ashton Coucher. Josh Grobin. Jeremy Piven

Bobby Flay Jason Siddakis Possibly Adrian Brody It's just like It's really a hit list of Yikes The Entourage cast 2 of 5

That is really brutal I can't support that She's Jeremy Piven And Adrian Grenier Oof But it's in a way It's glorious And it's badness

It's true It definitely fits What the profile She has created For herself in the tabloids So, you know, and also is splashiness and, like, me being able to name all the people that January Jones has dated. I know. It's, like, more impressive than anything she's done acting-wise.

Exactly. So there's, those are strong choices that I want to give her, like, a B-plus just for, like, flair. Yeah, I think she might even get an A. Okay. Plus, she has a mystery baby daddy, which is incredible. That's true. Like, it's hard to pull off. It's very true.

And her Instagram's very good. I just want to put that out there. It's actually, like, very funny. She has, like, a lot of, yeah, she's, like, a lot of, jokes like her life in L.A. getting her hair and her nails done. And baby pictures of her. She was just like a very, but also baby pictures of January Jones herself. Oh, really? She was quite, quite chubby and unusual looking. I don't know. She makes jokes about it, so I feel like it's okay. She was cute. But it doesn't look like January Jones now. It's really interesting. That's amazing.

Yeah. Good for her. And she has a good sense of humor about it. Yeah. She seems like, through mediated forms, like really enjoyable, but I don't know if I'd want to spend time with her one-on-one. Interesting. And also, she's now reportedly dating John Hamm. Not reportedly. I read that in some tabloids. Okay.

I don't know if it's true. How does it make you feel? Again, like I get it. Like, if you spend six years pretending to be, like, in some kind of relationship, even if it's a tortured one, like that just seems confusing to me. At this point, it's just like, it displays a lack of creativity, especially given everyone that she dated before,

I want people to reach for the stars. I want you to get weird with like a Silicon Valley dude. Or dare I say, a world leader, which leads us to our patron saint Wendy Dang. Wendy! Okay. As we've discussed in this podcast, formally married to Rupert Murdoch, alleged relationships with Tony Blair and the Google former like CEO, Eric Schmidt. You can read a Vanity Fair story about all of that.

We're not making it up. Recommend it. And now, according to Us Weekly, she's dating. Vladimir Putin of Russia. It's, I'm speechless. It's literally inexplicable. It's actually inexplicable. Like, I don't even know.

Like, does she speak Russian? How do they communicate? No idea. So this came out on March 31st. Yeah. Around noon, eastern time on March 31st is I think what it came out. And I know the time because I was just very afraid it was going to be an April Fool's joke. Me too.

I was very afraid that on Friday they were going to like take this way from us. And so far they have not. But it also hasn't like exactly been. It's all like sources. It's true. We don't have photo evidence, which as I said earlier is important to me. And no one has managed to come through with any evidence beyond the S Weekly Post. What a moment in history to get involved with the premiere of Russia? Like that's just really weird. Like Russia is like really involved in all these, this like semi-world war going on. And I just, how does he have time for dating? Exactly. I was going to say also, what are their dates like?

I don't know. How do you think they met? They probably met at some, like, state dinner. Not like a state dinner, but like a dinner with, like, heads of state. Like, I don't think, like, either of them was, you know, at a state dinner at the White House, but, like, that's, like, their scene. Sure. It's inexplicable. Like, what's, like, what do they do on a date?

Like, ride horses. I was about to say they ride horses is shirtless. Which is, like, the only thing. Is she shirtless, too? Sounds like a real Chelsea handler kind of date. I hope so. It's so weird. I just can't get over it.

Wendy Dang is one of a kind. She's one of one. It's just, it's a phenomenal dating strategy, a phenomenal set of tastes. And shout out to us weekly for making that a big story. Like, they're like, yes, this is something that we're going to publish. I just, like, I would put out a call to everyone else. I want proof. I want to know everything.

Picks or it didn't happen. Picks or it didn't happen. That's what the kids say. But also, I sort of feel like when, this makes kind of Wendy, Wendy Dang, one of the all-time greats. Oh, yeah. Like, that's up there with Warren Beatty level in terms of the, just the crazy list of people that you are dating.

Yeah, she's an A-plus. Like, this is A-plus level. It's a championship. Yeah. And now, no, you were so stressed out by this. You don't even know how to process it. It actually blows my mind that they're dating. What kind of security measures does she have to go through?

And, like, do they WhatsApp? Like, what's their preferred mode of communication in FaceTime? God, I don't even know. It's really, it's just hard to understand. Maybe their whole relationship takes place on private. That's a great way to have relationships, like luxury, swanky. I mean, clearly Wendy loves luxury. If her dating history tells anything, that's like only the best for her.

Respect. Yeah, I like luxury too. Who doesn't? Such a nice robe in the clutch of Vladimir Putin. I guess we should point out that like maybe like she doesn't do a lot of moral screening. No. I don't think she does. I don't know.

Or maybe her immoral compass is just different than ours. I guess. That's true. Open-minded. Either way. A plus for her. She's just doing the great work. So Wendy Day is the champion. Yeah. There's she, I def, I dare someone at the top her. Like, who's even in the conversation? No one. Maybe Derek Jeter.

No. No, he doesn't even have, he doesn't have any. Two world leaders. Two world leaders. It's true. Not one, but two. It's incredible. It's incredible. And not allies. Great job. Um, all right. And now it's time for our game, two truths and a lie. Are you ready? I'm ready. I'm quite nervous. I think you're going, I think I did a bad job. We'll see. I know, but we've learned that I kind of, I have selective memory. Okay. I've closed my computer. I'm ready to focus.

All right. Let's start with a man. Okay. Tofer Grace, here are three women. Oh, Jesus Christ. Two of whom he dated. Oh, God. Minka Kelly.

Okay. Piper Parabo. Wow. And Emmy Rossum. Wow. Okay. I'm going to think through this little with you. Okay.

Talk it out. You know, I feel Minka Kelly's dangerous because Minka Kelly has dated enough people. like Jeter and also there was like a Chris Evans moment. So it seems like she could, but I'm wondering if that's too dangerous. She seems like the obvious choice. Piper Parabo is delightful and I just want that to be true. Emmy Rossum, I don't know a lot about Emmy Rossum right now. Emmy Rossum right now is engaged to Sam S. Mail, the showrunner of Mr. Robot.

Oh, interesting. Yeah. She's a lady out in the world. I'm going to say that Minka Kelly is the lie. Incorrect. Damn it. It's Piper Pervo. No!

I wanted him to date Piper Pervo. It seems like she was the right era for him. Yeah. Okay. So he has a type, it would seem. Yeah, exactly. All right. That's what I was thinking to.

I was like, oh, Minka Kelly and Emmy Rossum. They're the exact same person. Okay. All right. Next, a woman, Natalie Portman. Okay. Jude Law. Wow.

Lucas Haas. Wow. And Julian Casablancus. Did you, maybe you just, did you know, did you know, that I love Julian? No, I did. Okay, so I love Julian Casablanca. I did not know that. Julia Casablanca. So you just love the strokes? I love the strokes, which is strange because I normally hate guitar music. But again, like, I was not quite as young as you, but strokes were formative experience when that came out. And I love him. And I, you're claiming that you don't

know that, but maybe you did and you just put him in. No, I didn't know that. Um, okay. I would love Lucas Haas to be true for just obvious reasons. I wish Lucas Haas was like, a little bit more famous. Like, he's famous to people who love celebrity culture, but he's not, like, really famous on his own anymore. That's true. He's just... Like, what can we...

He needs a reality show. Duh. That'd be great. Why hasn't Leo Greenlit that through Appian Way yet? I feel like Lucas Haastho is the piper parabo of the situation where I just, like, wanted to be true because it's funny, and maybe it's not true. And who is the third person? Jude law?

Jude law. Like, Circa closer. That's their closer. Closer. No. Jude law is. the lie. Incorrect.

It's Julian Casablancus. Did you know? No. Was that a fakeout? Oh, I didn't know. Okay. I hate losing. This is really upsetting.

Lastly, Shia LeBuff. Oh, my God. Our one true king. Oh, maybe he can, yeah, okay. Rihanna, Robin, Rihanna Fenty. Okay. Megan Fox. Okay.

And Kieranightly. Huh. Wow. All right. So I know that the Megan Fox thing is true. true. Okay. Because I remember the profile where he like insinuated it at great length and people were very angry. I mean, dating is like a loose term there, but. Sure. I'm looking forward to revealing my strategy for crafting this for you for you. This is really stressful. Now I understand

what it was like when you're in the hot seat. I know, it's a lot of pressure. He dated Carrie Mulligan and I wonder whether you're trying to psych me out with Kira and Carrie. Just, you know, it's not a psych out. Yes, it is. There's nothing malicious. And I'm trying to win. But, you know, because like Kieran and Carrie, same vibes, same face shape, both in Pride and Prejudice, 2005. Great movie. Great movie. I saw it when I was in college.

I was like this weird thing where I remember every movie I saw and where I've seen it. Okay. I think it's because I don't know why. But like, every time I'm moving, I'm like, I know where that was. I know where it was and I saw it. Because film matters to you, Julia. Yeah, film matters. And Rihanna, again, like I guess we're using dating.

loosely. Loosely. And Rihanna... It's dating based on who's dated who. Rihanna post-C-B, who I will not mention, like pretty good streak. He should have been. Yeah, totally. She's in her own class of her own, though.

Drake Leo, that handsome baseball player. Matt Kemp, very handsome. Yeah. Matt Kemp of the Beats commercial. But, like, I believe that Rihanna could have just, like, gone for shy. Rihanna has a sense of humor, and Shaya would fit into that. She does. She seems like a fun girl.

But also if Rihanna and Shia had dated, I would know that because Shia is so important to us. So, final answer, I'm going to say that Rihanna's the lie. It's Kira Knightley. Damn it! I want to move from Rihanna and Shia. You figured out my strategy. I just picked one person and I was like, who's the like adjacent to this person? So Carrie Mug and Kira Knightley.

Okay. Piper, Parabo, I was just like, who was someone who was famous during that 70s show era? That's why I picked her. And Julian Casablancus, I picked because she. dated Fat Fadmaredi as well. Oh, right. I should have known that. This is like the answers are right there. Wait, hold on. Can we go back to Shia and Rihanna for a second? Yeah, sure. You need a picture? Yeah. Okay. I like when, what era, what, what happened? Shia's, they're both, they are king and queen of my heart, maybe. They're both great. They had one date. Okay. Shial above dated Rihanna.

That's like, there's like a few things that pop up. And that was enough to land on who's dated who.com. All right. Thank you for playing, Amanda. You're so welcome. We're both O for three, which feels great. It does. We're still on the same level playing field. Teammates.

Forever. Thanks for listening to Jam session. We'll be back next week. Wendy Dang. Cheers to you. Thanks again to Simply Safe. Most home security companies just make your life worse. They drill holes in your walls to install an outdated system,

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