Gwyneth Paltrow Makes Rare Comment About Past Ben Affleck Romance

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Gwyneth Paltrow likes them apples.

You know, Good Will Hunting is a movie I really cherish. It’s special to me because it was written by and starred Ben Affleck and Matt Damon – two people I’ve known for quite a while!

Gwyneth Paltrow told Amy Poehler on the January 6th episode of the Good Hang podcast that she’s a big fan of the movie, calling it ‘perfect’ and saying she loves it a lot.

Oh my gosh, I always knew Julia Roberts was amazing, but did you know she worked with Robin Williams way back in Hook? It wasn’t until Ben Affleck and Matt Damon got him on board for their movie in ’98 that they really connected, though. That’s when they actually became friends! It’s just… everything about that era is magical, and knowing they formed a bond then makes it even better. I’ve read everything about them, and that movie seems like such a turning point!

Gwyneth Paltrow said she only knew Robin Williams a little, getting to know him when Good Will Hunting was released. She was dating someone involved in the film – both as a writer and an actor – at the time. Williams passed away in 2014 at the age of 64.

Gwyneth Paltrow began dating Ben Affleck in 1997, shortly after ending her relationship with Brad Pitt. They dated on and off for about three years, until 2000.

And, according to the Emma star, each man brought something different to the bedroom.

 

Looking back, Brad was totally my everything – the intense, passionate kind of love you dream about, honestly. That’s how it felt at the time, as I told Alex Cooper on Call Her Daddy. But with Ben, it was different. He was just… incredibly skilled and talented, in a more measured way.

Gwyneth Paltrow revealed she’d remarry her ex-husband, Chris Martin, if she had to pick one of her former partners. She shared this while playing a game of “Fk, Marry, Kill” on the podcast hosted by Alex Cooper. Paltrow and Martin share two children, Apple, 21, and Moses, 19.

 

Gwyneth shared that her two children, whom she deeply loves, are a result of her relationship with Martin. Despite finalizing their divorce in 2016 and later marrying Brad Falchuk in 2018, she says she wouldn’t change having had those children.

And between Affleck and Pitt, the Goop founder chose the latter for the  “f–k” option.

She jokingly added of Affleck, “God bless him.”

For more celebrity couples you may have forgotten about, read on…

Although they portrayed tragic couples in the films Too Young to Die? (1990) and Kalifornia (1993), the actors themselves enjoyed a happy and healthy relationship off-screen.

Brad Pitt revealed in a 1995 interview with Vanity Fair that he still had feelings for his former partner. Reflecting on their relationship, which began when they attended the 1992 Oscars together after her Cape Fear nomination, he described her as a brilliant person and said they shared a wonderful time together. He considered it one of the best relationships of his life, but acknowledged the idealized notion that love always solves everything isn’t realistic.

It wasn’t just a nostalgic fantasy – Ben Affleck and Jennifer Garner really were a couple at the end of the 20th century. The story goes that they met thanks to Gwyneth Paltrow, who famously dated Ben’s close friend, Matt Damon. They ended their relationship in 2000.

Years later, in a 2004 interview with Playboy, Damon described Ryder as a “wonderful person.” Ryder, in turn, told Black Book in 2009 that “Matt is one of the kindest, most genuinely nice guys, and I feel fortunate that we remain friends.”

Cameron Diaz and Justin Timberlake had a noticeable connection when they presented together at the 2003 Kids’ Choice Awards. They dated for nearly four years, and their split in 2007 was announced with a formal statement emphasizing their continued friendship, love, and respect for each other.

While self-love is the most important relationship, actress Kristin Davis, known for her role in Sex and the City, enjoyed dating Alec Baldwin during her time on the HBO show.

On the February 2025 episode of the Literally! With Rob Lowe podcast, Kristin clarified that a former boyfriend – who she’d previously lent $5,000 to before he ended their relationship – was absolutely not the three-time Emmy winner people were speculating about.

Kristin recalled that when she dated Alec Baldwin, he was already very wealthy. She jokingly added that she would have never had to loan him $5,000 if that had been the case.

Kerry Washington, known for her role on Scandal, was featured on the cover of InStyle Weddings in 2005 while engaged to actor Boris Kodjoe. However, the couple ended their engagement in 2007.

Madonna didn’t publicly talk about her relationship with the rapper, who died in 1996 at age 25, until 2015. During an interview with Howard Stern, she explained that when she appeared on David Letterman’s show in 1994, she was dating Tupac and he had a way of getting her excited about life.

Before marrying Jim Toth, Reese Witherspoon starred alongside Jake Gyllenhaal in the 2007 thriller Rendition, and the two dated for about two years, following her divorce from Ryan Phillippe.

Jake spoke fondly of his ex, saying, ‘She’s one of the most intelligent and resilient people I know – and that’s true of many of the women I’ve been close to.’

In her 2025 memoir, My Good Side, the former Vanderpump Rules star shared details about her relationship with the Desperate Housewives actor, which happened in the mid-2000s.

She described how they’d often have dinner with his parents at his home. When they were alone, he would play guitar and sing to her, often performing ‘Hey There Delilah.’ She said it felt like she was living in a dream come true with someone she’d admired on screen for years.

Before marrying Livia Giuggioli in 1997 (they later separated in 2019), Colin Firth was in a relationship with Tilly for five years. They had a son, William Joseph Firth, who was born on September 20, 1990. William is also an actor and appeared alongside his father in Bridget Jones’s Baby.

As a lifestyle expert, I remember when everyone was buzzing about the U.S. Open champion dating Mandy Moore back in 2003 and 2004. It seemed like a sweet pairing, but sadly, it just didn’t turn into a lasting romance.

In 2018, Mandy Moore shared with Howard Stern that a past relationship had been very painful. She explained that she began dating him at 18, and he broke her heart. She added that they were both young at the time.

Everyone wonders who inspired Alanis Morissette’s famous 1995 song, and many people think it was the star of Full House! Morissette said it wasn’t true in a 2021 documentary called Jagged, but a lot of people find that hard to believe.

Back in 2005, Reynolds told People magazine that he was a big fan of his then-fiancée’s music, joking that it was a little embarrassing when she’d walk in on him listening to it and dancing in his underwear.

The Canadian band ended their run in 2007, and their split after four years was remarkably amicable.

It’s no surprise the actress from Mad Men is attracted to comedians. She dated Jason Sudeikis for a few months in 2010, and later had a brief relationship with Will Forte five years later.

As a lifestyle expert, I always find it fascinating when on-screen chemistry translates to real life. That was definitely the case with the stars of Good Will Hunting – Matt Damon and Minnie Driver actually dated! Sadly, their story wasn’t a Hollywood ending; they didn’t end up together in the long run, despite how perfect they seemed.

Damon shared on The Oprah Winfrey Show in January 1998 that he was currently single. He explained that he and Minnie had previously been in a relationship, but they had since become just friends, remaining very close and caring for each other. He acknowledged that, despite their connection, they weren’t meant to be a couple, and he accepted that.

Driver didn’t appreciate how publicly Matt announced their breakup. She later told the LA Times that his appearance on Oprah felt like a very inappropriate way to share such personal news. She thought it was unfortunate he chose that platform to announce they were no longer together.

Liam Neeson and Helen Mirren first met while filming the 1981 movie Excalibur. They later became a couple—Neeson recalls Mirren teaching him how to drive—but their relationship ended in the mid-1980s.

In February 2023, Liam Neeson told ET Canada he felt incredibly fortunate to have shared three or four years of his life with her, describing her as exceptional.

Finding love in Jurassic Park? What a meat cute.

Jeff Goldblum and his co-star started dating after they finished filming their hit 1993 movie. Goldblum told the Chicago Tribune that he’d been a longtime admirer of her talent and personality, saying he was immediately impressed and they discovered a mutual attraction once filming wrapped.

The couple became engaged in 1995, but their relationship didn’t last, and they broke up two years later. They shared the screen together again for the first time in 2022’s Jurassic World: Dominion, which was the sixth movie in the Jurassic World series.

Gillian Anderson, known for The X-Files, dated the creator of The Crown from 2016 to 2020. In 2020, she won an Emmy Award for her portrayal of Margaret Thatcher in the popular Netflix series.

According to Arquette, the two dated while filming their 1995 Western Wild Bill.

During a Reddit Q&A in November 2015, the actor from Clueless admitted to a surprising past relationship with the actress. They had previously appeared together in the 1992 TV movie Desperate Choices: To Save My Child.

She was the first actress I ever dated. We were together for a while, even though we lived far apart, and I was really crazy about her.

TopMob News was the first to report in 2015 that a star from The Real Housewives of New York was dating an actor from Modern Family. However, the pair broke up the next year.

The former student of Southland High and the actor known for playing Theo Huxtable on The Cosby Show were a couple for several years but broke up in 2013.

Before he became widely known, the celebrity was already living with Preston in 1987. They shared a home and even a pet pig named Max, but their relationship ended in 1989.

Oh, absolutely, Cher truly believes in finding love again! It’s amazing to remember that she and Kelly McGillis actually dated back in the 80s, after Cher had gone through her divorces from Sonny Bono and Gregg Allman. It’s a little-known but wonderful part of both their histories.

Before he was Heidi Klum‘s ex, the “Kiss from a Rose” musician romanced a different supermodel.

The pair apparently began dating after they met while filming the 2005 movie Brick, but their relationship only lasted about six months.

The Dawson’s Creek alum and the Josie and the Pussycats star dated for about a year back in 2002.

Reese Witherspoon and the star of NCIS: LA began dating in 1993, shortly after Witherspoon moved to Los Angeles at age 17.

Robert Downey Jr., known for playing Iron Man, has spoken openly about how his struggles with drugs and alcohol led to the end of his seven-year relationship with Sarah Jessica Parker. In a 2008 interview with Parade magazine, he explained that his lifestyle was incompatible with hers, as she doesn’t share those habits. He also shared that Parker tried to help him, but was frustrated when he couldn’t overcome his issues.

Matthew Perry, best known for Friends, and The Hangover star reportedly had a brief romantic encounter in 2003, but it was just a quick fling and didn’t develop into anything serious.

Kat Dennings, known for her role in 2 Broke Girls, had a short romance with her Thor co-star in 2010. They seemed very close while promoting the Marvel movie at Comic-Con, but the relationship ended before the film was released the next year.

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2026-01-06 23:18