Inside Gwyneth Paltrow's Relationship with Ben Affleck

Who: Oscar winning actress, lifestyle guru, and businesswoman Gwyneth Paltrow, 46, and two-time Oscar winning actor and director Ben Affleck, 46.

How They Met: Ironically, the young and wildly famous duo met at a dinner hosted by the now notorious producer Harvey Weinstein back in 1997. They went on to star in two films together: Shakespeare In Love (which would land Paltrow her first Oscar) and rom-com Bounce (which didn’t have quite as impressive an awards season turnout).

Why We Loved Them: They were just so young and fresh exuding of promise — if we didn’t know better, we’d have assumed their collaboration on "Bounce" was as brand ambassadors for the dryer sheet company.

When They Peaked: In this photo, of course:

The Breakup:

As beautiful and accomplished as they both were, Beneth was, sadly, not built to last. Paltrow was fresh out of a long-term relationship with (and engagement to) Brad Pitt, and Ben was honestly kind of a rebound. “I just think we have a very different sort of value system,” Gwyneth said of her ex. ”Ben makes life tough for himself. He’s got a lot of complication, and you know, he really is a great guy. So I hope he sorts himself out.”

Though Paltrow once described Affleck’s “perfect woman” as “any sort of stripper at Scores. Anyone that serves cold beer in a bikini,” she still holds her former beau in high esteem. In 2015, she told Howard Stern that she and Ben were still friends. “I like him,” she said.

Another sign it wasn’t quite meant to be? Her parents weren’t sold on the union. While mom Blythe Danner and Gwyneth’s late father, Bruce Paltrow, were wild for Pitt, they weren’t quite as jazzed about Ben. "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 told Stern in 2015. "I think they were OK with the two of us not being together."

Looking back, though, Paltrow sees the importance of her relationship with Affleck. “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 explained. "I’m not sure exactly what I was trying to heal in that instance, but it was ... he was, ya know, it was specific."

Where They Are Now:

The split was hardly a bump in the road for Ben and Gwyneth.

Paltrow went on to star in a slew of critical and commercial successes and build a lifestyle brand that’s become something of a cultural touchstone.

After dating Affleck, Paltrow met Coldplay front man Chris Martin, whom she wed in 2003 and welcomed two children with: Apple, 14, and Moses, 12. Though she and Chris “consciously uncoupled” in 2014, they remain close — as in, like siblings (not weird at all). Paltrow is currently engaged to producer/writer/director Brad Falchuk.

Affleck’s oeuvre evolved considerably through the 21st century. Not only did Affleck star in films like Daredevil, Gone Girl, and Justice League, but he directed hits like Argo, The Town, and Gone Baby Gone.

Post-Gwyneth, Ben dated (and was engaged to) Jennifer Lopez. After their split, Ben moved to a new Jennifer: Garner. Ben and Jen 2.0 wed in 2005, welcoming three children: Violet, 12, Seraphina, 9, and Samuel, 6. In 2015, Garner and Affleck announced their split. Ben went on to date SNL producer Lindsay Shookus, and is currently spending time with Playboy model Shauna Sexton.

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