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Ben Affleck is back in the headlines thanks to his rekindled relationship with ex-fiancé Jennifer Lopez. Prior to his marriage to Jennifer Garner, Affleck also had an on-and-off romance with Oscar winner Gwyneth Paltrow from 1997 to 2000. The Iron Man star commented on her past coupling with Affleck in some previous interviews, where their final split didn’t appear to be too much of a heartbreak.

Ben Affleck and Gwyneth Paltrow at the premiere of 'Armageddon'
Ben Affleck and Gwyneth Paltrow | Ke.Mazur/WireImage

Gwyneth Paltrow felt Ben Affleck had ‘complication’ in his life

Paltrow and Affleck were introduced by now-disgraced Hollywood producer Harvey Weinstein and began a three-year on-again, off-again relationship. While Paltrow once said that Affleck’s “perfect woman” would be “any sort of stripper at Scores; anyone that serves cold beer in a bikini,” she explained her view of the Good Will Hunting star a little more clearly in a 2003 interview with Diane Sawyer.

“Ben makes life tough for himself,” Paltrow told Sawyer. “He’s got a lot of complication, and you know, he really is a great guy. So I hope he sorts himself out. … I just think we have a very different sort of value system.”

The two shared the big screen in the films Shakespeare in Love and Bounce, and ended their romance for good in 2000. Affleck began dating J-Lo and the couple was engaged in 2003, yet parted ways the following year. The actor married Daredevil co-start Jennifer Garner in 2005, though the pair divorced in 2018. Affleck and Garner continue to co-parent their three kids.

Gwyneth Paltrow talked to Howard Stern about her relationship with Ben Affleck

Paltrow has been a frequent guest on Sirius XM’s The Howard Stern Show. In 2018, Stern asked about her relationship with Affleck and if she had even been in love with him.

“It’s interesting, I think there’s certain boyfriends where you are trying to work stuff out, right?” she explained. “Like, you’re trying to heal certain stuff from your childhood and he was very much a lesson in that way. I’m not sure exactly what I was trying to heal in that instance, but it was… he was, ya know, it was specific.”

On another episode of Stern’s show, Paltrow noted that her parents — Blythe Danner and the late Bruce Paltrow — never expected her romance with Affleck to last.

“I think [my parents] appreciated how he’s super intelligent and he’s really, really talented and so funny, but he was not in a good place in his life to have a girlfriend,” she shared in 2015. “I think they were OK with the two of us not being together.”

Paltrow also referenced her previous “stripper” comment on Affleck, saying, “Well, that was true at the time!”

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The Marvel star went on to marry Coldplay frontman Chris Martin. The couple split in 2014 and share two kids — Apple, 17, and Moses, 15. Paltrow is now married to TV writer/director Brad Falchuk, and told Stern she was ready for the commitment this time around.

“I think that I would like to give it a proper shot … for myself,” Paltrow said in 2018 of heading to the altar again. “I think there’s something really beautiful about marriage. I think Brad is someone who is really intelligent, he’s very emotionally intelligent; I think he’s a really good person to try this with. He’s very self-aware. He’s got a lot of emotional maturity.”

Paltrow and Falchuk will celebrate their third wedding anniversary in September.