There is no denying that Gwyneth Paltrow has had one hell of a past! The Mortdecai actress looked back on her illustrious Hollywood history on Howard Stern's SiriusXM radio show on Wednesday, Jan. 14, contemplating why her relationships with exes Brad Pitt and Ben Affleck did not work out.
Paltrow, 42, was in her early 20s when she was engaged to Pitt in the mid-1990s. The stars first met on the set of 1995 thriller Seven, and dated for nearly three years. "I definitely fell in love with him," she recalled of Angelina Jolie's now-husband, 51. "He was so gorgeous and sweet. I mean, he was Brad Pitt!"
Equally in love with the actor was her late director-father, Bruce Paltrow, who saw Pitt as a son. "My father was devastated," she admitted to Stern of their 1997 split. "I was such a kid, I was 22 when we met. It's taken me until 40 to get my head out of my ass. You can't make that decision when you're 22 years old... I wasn't ready, and he was too good for me." To sum it up, she said: "I didn't know what I was doing."
Despite the painful breakup — which Paltrow confessed affected her for five years in a 2003 interview with Diane Sawyer — the A-listers still remain on good terms. "If I see him, we're friendly," Paltrow told Stern on Wednesday. "I don't hang out with him."
The actress added that she has several throwback photos of the two when they were together. "I have a couple somewhere," she revealed. "I think every piece of your life is an important piece of your life!"
Paltrow also opened up to Stern about another one of her famous exes: Affleck. "He was not in a good place in his life to have a girlfriend," the Iron Man actress said of her on-and-off boyfriend, now 42, from 1997 to 2000. Paltrow also costarred in a film with Affleck, playing his love interest in 2000 flop Bounce.
"I think that when you're in your twenties, you can get swept up in [good looks]," she noted of being with her hunky exes. "When you're a kid, you tend to be more shallow and you're also immature, so you think that being with a good looking person validates yourself in some kind of way. It's not true."
Unlike Pitt, Paltrow's parents knew that Affleck was not the right fit for her. "I think they appreciated how he's super intelligent and he's really talented and funny," she said of her dad and famous mom Blythe Danner. "They loved him, but they were okay with us not being together."
That time period was an interesting one for Paltrow, whose best friend at the time, Winona Ryder, was dating Affleck's closest buddy Matt Damon. The stars ultimately had a huge falling out after Paltrow allegedly stole the lead role in Shakespeare in Love from Ryder. Paltrow, however, addressed and denied the infamous rumor to Stern on Wednesday.
The actress has grown significantly since her 20s, confirming to Stern that she and her estranged husband Chris Martin are still friendly. The only regret she has from their breakup is using the now-infamous term "conscious uncoupling" to describe their separation in a Goop newsletter last March.
"I made a mistake," she said. "I didn't give it context. But it is a goofy term."