As they say, past behavior is the best predictor of future behavior, and so when it comes to soothsaying Jennifer Lopez and Ben Affleck’s shared future, we just need someone who knew them very well the first time around, right? We found that oracle in Rob Shuter.

The current voice and mind of iHeartRadio podcast Naughty But Nice With Rob Shuter was once the publicist for some very big names at brief, but crucial crossroads between their careers, their personal lives, and pop-culture history—notably, yes, Jennifer Lopez during Ben Affleck, Take One, but also Jessica Simpson during her divorce from Nick Lachey, Naomi Campbell during phonegate, and Paris Hilton at the height of her height. He’s also responsible for the press statements that confirmed the official end of both Lopez’s and Simpson’s relationships. 

And the garrulous Brit has nailed some extraordinary timing once again. His first book, The 4 Word Answer, had already been sent to the publisher when huge news broke: Jennifer Lopez and Ben Affleck were back together. Though the book has some details from back when he was on J.Lo’s payroll, it’s mainly a self-help guide drawn from what he’s learned from his shiniest former clients. Each successful person, he argues, knows themself by four simple words unique to them. By way of explanation, Shuter expounds on four different qualities, drawing from the pot of words assigned to his biggest former clients. One of Simpson’s is “smart,” for example; Lopez is, in part, “kind”; and Puff Daddy, Diddy, now Love, is “important” (they are inspired by exactly the movie you think, but you’ll have to buy the book to learn the fourth word). 

The book does not have much celebrity dish from his time among stars, though. “In this world, that’s fun cocktail stories,” he said. “And nothing’s more fun at a party than me telling some funny stories of Jessica Simpson. But I don’t think there’s a takeaway from that. And it’s certainly not worth $25. It’s worth maybe one vodka soda.”

In some parts of New York, where Shuter still resides, that’s how much a vodka soda goes for. But he gamely hopped on the phone to take advantage of the fortunate timing—our favorite celebrity faces of second chances have just come off a long vacation to make their red-carpet debut (Take Two). He paused and reflected on what he witnessed all those years ago, and what he expects for their future.

Take what you can now! According to a source at People, the couple’s fall is about to get busy. “They will see each other when they can,” this person said.

Vanity Fair: Did you read Jessica Simpson’s memoir? 

Rob Shuter: I did. I think it was extraordinary. I have a chapter of her and being smart in the book. She's the smartest person I've ever met, and I know people are going to laugh about that because she plays such a ditzy blonde. But I made the mistake growing up, just not thinking I was really that smart. I didn't get great grades at school. I failed my exam to go to Oxford and Cambridge and Edinburgh's a nice school, I'm glad I went there, but I got in by the skin of my teeth. Let me tell you that, like nobody was rolling out a red carpet for me and so working with Jessica, I remember early on just looking at her and being like you were. What is it? And it really was her willingness to try. Nobody has been knocked down more times than Jessica Simpson. 

I would have been that person that could [have] gotten 10 great reviews and one bad blog post. And I would have focused on the blog post for the rest of my days. And she taught me, don't do that. And I picked the positive way now. 

Even in her darkest hours—I was with Jessica when she broke up with Nick. I was actually the one that wrote the statement, that sort of generic, "We're friends and we want privacy." Like the standard PR statement. 

It's not in the book, but she did not have a prenup with Nick. When she first married him, Nick was the rich one, not Jess. And so there was never any prenup. I think at the time they got married, Joe Simpson must've thought it was a brilliant idea to not have a prenup because Nick was this big star in a pop group. Jessica's career had never really exploded as a singer. However, who would have known that she would have become America's favorite housewife and make all this money in endorsements. I remember when they broke up, Jessica had to give Nick an enormous amount of money and I was in a car with her the day she wrote the check and I was like, Oh God, this isn't going to be a good day and she looks at me in the eye and she said, “I made it once. I'll make it again.” I was just like, you're so smart. Instead of getting all angry and nasty and bitter about this it's over. She moves on. 

I like how you framed it in the book: The entire persona of the ditzy blonde was in response to her rival Britney Spears.

She knows what she's doing. I was in a car with her once going to an award show and she deliberately put a little bit of lipstick on her tooth. So when she smiled in front of the photographers, that would be like, oh God, like it was, it was all planned out. It was not by chance. 

Okay, who I really want to talk to you about is J.Lo... 

Good timing that was, right? 

Great timing. When did you start working with her? 

I started when she was with Ben. So she was dating Ben, it looked like they were going to get married, and then I was with her during the whole meltdown. And so what was that? I guess 2004? 2005? And like Jessica, I wrote the statement. So Jen was on the phone with me and we wrote the breakup statements, which I think again was very much about, "We still are good friends." (Not true.) "We respect our privacy." (Probably not true either). But it's that generic sort of publicist statement. And to be honest, we all Google each other, so when you have a client that breaks up, you think of the last star that broke up and you Google them. I was like who was the last star? Was it Sandra Bullock? And you pretty much use their statement as a prototype. And so I remember Googling the last big star that had broken up and going through it with Jennifer and she signed off on it.

What was your goal when they broke up? What did you want to do for Jennifer? 

Protect her. Because at the time, the information that we now know about Ben wasn't public knowledge. I think he's talked very openly and really passionately about his sobriety and his issues and his troubles and going to rehab. 

Although a lot of people in the business and clearly Jennifer knew about this, it wasn't in the public eye. However, my concern was not necessarily protecting him, but at the same time it was a secret that would have been explosive if the truth had come out and that made it very difficult. Everybody wanted to know why. I can't tell the truth. It makes your story really hard to tell. I do remember a couple of weeks later, she was set to present at the Golden Globes in LA and I thought she would cancel. So I called her, I was like, we should probably cancel now rather than the day before. 

And she said, no, I'm doing it. It was her first public appearance and I got there early in the afternoon and made all the arrangements for her to come through the side door of the hotel. It's just these little logistics that people don't think about, but you have to think like, where does the car pull-up? How does she get in? How do I get her from a door in the back of the hotel, probably by the kitchen to the ballroom to the stage. Is she going to sit in the ballroom or is she going to wait in the wings to come out and present this award? So all these details had been worked out. And about an hour before I got a call and it was her manager saying she's walking the carpet. 

She's been the master of her own image for so long. 

Oh, I felt guilty getting paid. Honestly, she was the boss though. And I've got to be really clear about that. A lot of times people think the publicist is pulling the strings. No, I was implementing her strategy. She knew what she was doing. She was the boss. I would have made the mistake whisking her in through a side door. And she was the one that was like, absolutely not. I'm walking in with my head held high. I'm presenting this award. I'm going to look amazing. And I'm going to steal all the press. 

When Jennifer and Ben broke up, did you have any sense that they would get back together? 

I knew it. I didn't think it would take this long, but remember Jennifer's the rebound girl. So after she broke up with Ben, she went running back to Marc Anthony. Jennifer's always been comforted by people from the past. She's never really ended her friendship with Diddy, and there's nothing there romantically, but Jennifer likes what she knows. 

And I knew it was still the love of her life. I knew the way she spoke about him. She was giddy. She was so excited if you were with her, and he called like, he was the love of her life. But I think I say this, you can't say sorry to Jennifer more than once [the] only apology she accepts [is] a change in behavior. And so Ben let her down and she just couldn't, she wasn't going to tolerate it. And I think now that he's gone and dealt with some of his demons, now he's ready to be with Jennifer. 

What makes them so compatible? 

I think they both understood each other. Like when you take away all the fame, they were both like working-class kids who had a lot of ambition and really, really fought hard to get to the top of their game. But at the same time, as fancy as they are they would still love a Dunkin’ Donuts. They knew each other. They could finish each other's sentences. They were comfortable around each other in a way that I don't think they were that comfortable with other Hollywood folks. 

So do you think these crazy kids have a shot at forever? 

I think they're going to get married and I think it's going to be a much smaller wedding than we all hope. I don't think it's going to be a big Hollywood wedding. I think it's gonna be a wedding of them and their family and their friends. And, um, I think I've got a real shot of it because they know each other and they're ready for each other. You know, it might be a cliche, but I love the Barry Manilow song [“Somewhere Down the Road” that says] ‘we had the right love at the wrong time’. And now is the right time. They have the right love. They always had the right love. It was the wrong time. Now I think it's the right time. 

Do you have a prediction for when the proposal might happen? 

It'll happen at Christmas in Wyoming—[laughing] it's so specific—Christmas in Wyoming with the kids involved. 

Love the specificity. Why do you say that? 

I think because this is her moment for her and Ben. And so I think she's going to get away from the Hollywood New York gang that never really sort of supported her that much. I think this is because it's the second time around. It's going to be their moment together. Although they clearly still do enjoy the attention. Like a couple of days ago, they walked through Washington Square Park for no reason, apparently rather than just to have photographs taken. If you look at the footage from two days ago, it's outside her house on 26th street, she just got dressed up to the nines. Like, let's go for a stroll. 

So maybe we'll get a flash of the ring from Wyoming, but I think they get it. I think they're going to go away together and I will bet at Christmas. 

Do you think that he would propose with a new ring or is the old ring somewhere in the mix? 

This annoys them. So I recently mentioned that when I was working with her, that she had not given the ring back and I know it because several times reporters asked me what happened to that ring. It became such a story and I'd ask her where's the ring. And she would never, ever confirm that it had been given back or given to a charity. It was made clear to me that Jennifer's new team did not appreciate this conversation. So I would, I would predict it's going to be a new ring and they'll never mention the old ring. 

I was reading a bunch of the coverage from the first time around, and I was reminded that the press wasn't always rooting for them. What do you think changed?

I think there's some racism to the press back in Jennifer's day. I remember that Golden Globes that we were talking about a moment ago, and other celebrities were whispering, and making fun of her, gossiping. When I was backstage in the press room with all the other publicists, they didn't want to sit with me. I was J.Lo's publicist. And this was before the Kardashians. This was before the Real Housewives. This was before reality TV. And back then celebrities with big bottoms would have had their stylists find something to cover it. Jennifer never did that. She turned up and she was J.Lo. And the other stars were sort of a little bit snobbish about it.  

I think too, a lot of celebrities hated the fact that she was turning up at these award shows and not winning. She wasn't even nominated and she was getting all the press. I literally saw celebrities hiss. They were not kind to her.

I guess you're not going to name names, right? 

I remember like we were walking down a carpet and Streisand arrived before Jennifer and the fact every TV crew dropped Barbra to get B-roll of Jennifer did not go over well. 

I don't think it was a rivalry. It was just, nobody had seen this ball of energy and I was sort of used to it. When Jennifer goes to an event, we're used to the pandemonium back then they were not, there was no Kardashians. This was before that world had exploded and people thought it was vulgar or, or, or cheap. They were there for the arts. They were there to be celebrated as actors. And she was like, I'm going to turn up and look fabulous. 

I remember I went to the gym with her once, [when] she works out, she works really, really hard. And you know, I think I say in the book that effort is the only currency of success. Nobody works harder than Jennifer Lopez. 

This headline has been updated.

More Great Stories From Vanity Fair 

— Met Gala 2021: See the Best-Dressed Stars on the Red Carpet
— The Trials of Diet Prada
— Emmys 2021: See All of the Red-Carpet Looks
— Anthony Bourdain’s Longtime Director and Producer Releases Memoir
— The 2021 Met Gala’s American Theme Winners: Who Did It Best?
— Inside the Hermès Workshop That Makes Its Iconic Bags
— Love Is a Crime: Inside One of Hollywood’s Wildest Scandals
— The Best Beauty Moments From the 2021 Emmys
— Ted Lasso: How to Dress Like Keeley and Rebecca
— From the Archive: Influencers on the Coast of Utopia
— Sign up for “The Buyline” to receive a curated list of fashion, books, and beauty buys in one weekly newsletter.