Ben Affleck and Gwyneth Paltrow: From Perfect Couple to Just Good Friends

Since both of them now have a string of high-profile exes behind them, the three year on-off relationship between Ben Affleck and Gwyneth Paltrow at the tail end of the 20th century has been overshadowed by the many romantic dramas in their lives since. But, over the years, all sorts of interesting details have emerged about the cute but ultimately ill-fated romance between two of Hollywood’s most intriguing characters…

How it Began

Just weeks apart in age and both part of the same young, talented, late ‘90s Hollywood set, the pair were both 25 when they first met at a Miramax dinner in 1997 (and not at the premiere of Affleck’s breakthrough movie Good Will Hunting later that year, as has often been reported.)

At the time, Paltrow — then best known for her roles in Seven and Emma — was freshly single and ready to mingle after calling off her engagement to Brad Pitt a few months earlier, while Affleck was newly famous and had recently split from his summer camp sweetheart and girlfriend of seven years, Cheyenne Rothman (then an aspiring director herself, now a full-time mom who prefers being out of the spotlight.)

Soon, Paltrow and Affleck were going on double dates with another iconic but short-lived ‘90s couple, Winona Ryder and Matt Damon, and indulging in red carpet PDAs. Two gorgeous, talented, intelligent stars whose movie careers were going stratospheric at the same time — what could possibly go wrong?

How Long it Lasted

While on paper, these two were a great match, it seems they weren’t quite at the same life stage mentally, with Paltrow looking for something a little more settled than Affleck could offer at the time, as he revelled in his new VIP status on the wild Hollywood party scene.

Still, they were together for almost three years in total, but it was an on/off situation that eventually fizzled into a strong friendship when they finally split for good in 2000.

Their relationship was a very busy one, with the pair co-starring in two movies together — 1998’s huge hit Shakespeare In Love (yes, the one that Paltrow would go on to win the Best Actress Oscar for in 1999) and the more low-key romantic drama, Bounce (they were in more of an “off” phase while shooting it, though, and by the time it was released in 2000, they had split properly.)

How it Ended

By the time Bounce came out, they were over, after realizing they didn’t want quite the same things. “I can tell you unequivocally that Gwyneth and I are not going out,” Affleck told Entertainment Weekly in 2000 when asked about paparazzi photos of him hugging Paltrow in Paris. “We’re not a couple. We’re not an item. I do love her very much and I care about her enormously, as that picture indicates. But I hug a lot of people this way. Whether or not people believe that is up to them.”

(It’s official, Affleck is a hugger — we saw the same thing again recently when he was hanging out with one of his other very high-profile exes, former wife Jennifer Garner, at their son Samuel’s paintball party in March 2025.)

Paltrow confirmed the split at the time, too. “If we’re in the same city, we go out,” she told Entertainment Weekly. ”We’re close. Sometimes when I’m in L.A., I stay in his house. But it’s not what people think it is. We are not together. I swear on my life. We’re not. It’s really art imitating life, only without the happy ending in our case. But we have another kind of happy ending, which is that we have a friendship. I love his family, even more than I love him. So that’s a good thing.”

Even during the relationship there were signs that they weren’t quite on the same page — but they were at least funny about it. When they appeared on Good Morning America together in 1999 while dating, Affleck said that Paltrow’s ideal man would be someone like her dad, and Paltrow hit back that Affleck’s perfect woman would be “any sort of stripper at Scores, anyone that serves cold beer in a bikini.” Of course, we all know that Paltrow is more the type to serve kombucha in crisp white denim.

Despite their differences, they admirably got through the break-up in good spirits too. During a Saturday Night Live appearance to promote Bounce, Affleck popped up during a scripted skit with Paltrow. “We just broke up a month ago,” he reminded her. “Didn’t you read about it? It was in all the papers!”

What They Said About Each Other

While they were together, Paltrow was openly gushing about her man. “He’s the most intelligent man I’ve met under 45,” she told the Los Angeles Times in 1999. “He’s a brilliant actor. He has a huge range and impeccable timing and real depth. I think it’s great that it’s coming out slowly, bit by bit.”

In 2000, around the time they finally split, she was also extremely complimentary about her on/off love in an interview with the New York Times. “Ben is affable and charming and people are sort of drawn to him,” she said. “He’s disarmingly quick, fiercely intelligent and, in some ways, an underachiever. Ben had a difficult childhood, but not a nightmarish one. He loves both his parents dearly. Though Ben had almost perfect SAT scores in high school, his grades varied wildly depending on his attendance and level of interest. There’s a huge chasm between the public and the private Bens. In quiet moments, Jocular Ben transforms into Contemplative Ben. He’s not vulnerable right away; it takes ages to get to that part of him. I like him in all his incarnations.”

It wasn’t just Paltrow doing all the talking — while Affleck wasn’t quite as effusive (who is?!), he often praised Paltrow for helping him professionally. “One of the things that Gwyneth taught me is to maintain a level of work where interesting people that you like want to work with you,” he said in the same interview, to promote Shakespeare In Love. “And you do that by doing things you think are interesting, not by playing into some expectation.”

What They Say Now

Since the split, the pair have been probed about their relationship from time to time and both have been happy to talk about it, with their feelings of friendship seemingly getting warmer and warmer over the years as they moved on with new partners (actor Luke Wilson was Paltrow’s next, relatively brief, relationship. She then married Chris Martin in 2003 and had two children together — daughter Apple, born in 2004 and son Moses, born in 2006 — before “consciously uncoupling” in 2014 and going on to marry current husband Brad Falchuk in 2018. Affleck, meanwhile, was with Jennifer Lopez from 2002 to 2004, before they called off their engagement, and then spent a decade married to Jennifer Garner and had three children — Violet, Fin and Samuel — before their split in 2015. He and Lopez then shocked the world by getting back together in 2021, but divorced after two years of marriage. He is currently single.)

In 2000, not long after their split, Paltrow talked about how she often tried to push Affleck to take on tougher roles. “I’ve always had this ongoing dialogue with Ben about doing stuff that required more of him,” she told Entertainment Weekly as the pair promoted Bounce. “When I see something like Armageddon and see him just not connecting, I get sort of like, ‘Yeah, you’re charming… but it’s not what you’re capable of.”

She added: “We didn’t have one of those horrible acrimonious break-ups. The good thing is that we maintained this friendship. I have a sort of brotherly feeling towards him. I want him to do well and grow up and be a happy person and a fully realised man and feel good about himself, so when I read the script I thought, ‘Ben has to do this film. It would be really good for him to have something where he has to really sink his teeth in and concentrate and expand.’ I mean, everyone thought, ‘Don’t do this. You’re making a real mistake. It’s going to be a drama.’ My father was like, ‘Oh, God!’ I don’t think he actually vocalised anything but I saw that look: ‘This is a mistake.’ But it couldn’t have been better. We’re so fond of each other and we have such a nice rapport between us. It wasn’t difficult at all. People just deal with things in different ways.”

In 2002, a couple of years on from the split and after Affleck had received treatment for alcoholism and was first rumored to be dating his future ex-wife Lopez, he talked to the Daily Mirror about how his lack of maturity had led to the split. “Gwyneth is much more evolved spiritually than I am,” he said, hinting at the Goop-ification that would follow. “She does yoga and meditates, and I just don’t. She is much closer to inner peace and has a sense of calm, whereas I am much more frantic and I need to be active. I have a very difficult time sitting still. We are very different in that respect, but she is still one of my closest friends.”

In a 2003 interview with Diane Sawyer, Paltrow was a little more negative about Affleck. “Ben makes life tough for himself,” she said. “He’s got a lot of complication, and you know, he really is a great guy. So I hope he sorts himself out.”

Affleck responded in 2004 via Rolling Stone, saying “She’s probably right about that. I trust her opinion about most things. Not all, but most. I think I probably do get in my own way.”

In a 2015 interview with Howard Stern, Paltrow was more reflective and analytical about the relationship. “He was not in a good place in his life to have a girlfriend,” she said. “It’s interesting, I think there’s certain boyfriends where you are trying to work stuff out, right? Like, you’re trying to heal certain stuff from your childhood and he was very much a lesson in that way.”

She added that her parents were big fans of Affleck, but understood why they split. “I think [they] appreciated that he’s super intelligent, and really, really talented,” she said. “And he’s funny. They loved him but they were okay with us not being a couple. I like him. I’m friends with him still.”

At the time, Affleck was married to Garner, and Paltrow said she was happy for them. “Not only is she beautiful, she’s so warm, and she cooks, and is so into her kids,” she said. “She’s really great and she’s hilarious. I had a girls’ dinner before the summer and she came over. She’s my neighbor. I really like her a lot.”

Since then, Paltrow and Affleck have always talked fondly about each other — in some cases, very fondly, when, on the Call Her Daddy podcast in 2023, she was asked to compare him sexually with her other most A-list of exes, Pitt.

“Brad was like the sort of major chemistry, love of your life, kind of, at the time and then Ben was, like, technically excellent,” she said. “I can’t believe my daughter is listening to this!” (Sure enough, Apple was in the studio too, with footage later shared of the teenager looking shocked with her hands over her ears!)

Paltrow added that Affleck was “a good kisser” and then referenced his brief marriage to Lopez which was in full swing at the time. “God bless J.Lo and everything she is getting over there!” she said with a laugh.

She added that Affleck was the funniest of her two big Hollywood exes (the other being Pitt, of course), but also the more argumentative.

Key Relationship Takeaways

These two were perfect peers, but not so perfect as a couple. But, despite Affleck’s apparent lack of maturity when it came to their relationship, they managed to deal with the breakup with the thoughtfulness and class they’re both known for — which is why they can now enjoy a solid friendship at 52 (but whether that makes Affleck the most intelligent man Paltrow has met over the age of 45 remains a mystery!)

Their friendship is definitely good news considering they just can’t seem to escape each other: while they’re no longer starring in the same Hollywood movies together, now their kids are rubbing shoulders instead: Affleck’s daughter Violet and Paltrow’s stepson Brody are both currently in their freshman year at Yale.

While Paltrow seems very settled with Falchuk, Affleck is, once again, single — but, knowing Paltrow, she’ll have a long list of gorgeous friends lined up for him. Well, it would be a shame for those “technically excellent” bedroom skills to go to waste, right?