Gwyneth Paltrow boosts a very impressive list of former boyfriends, and before marrying her estranged husband Chris Martin, the 42-year-old actress was in lengthy relationships with two of Hollywood's biggest stars, Brad Pitt and Ben Affleck.

Gwyneth Paltrow
Paltrow was in relationships with Brad Pitt and Ben Affleck during her 20's

Paltrow recently spoke candidly about what went wrong in her relationships with the A-listers during an interview with Howard Stern's SiriusXM radio show on Wednesday (Jan 14th), while promoting her new comedy 'Mortdecai.'

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The 'Iron Man' actress began dating Pitt in her early 20's after they met on the set of 1995's thriller 'Seven.' The two got engaged in 1996, only to split up nearly a year later. "I definitely fell in love with him," she recalled of the 51-year-old. "He was so gorgeous and sweet. I mean, he was Brad Pitt!"

Brad Pitt
Pitt proposed to Paltrow in 1996

Paltrow's father, late director-producer Bruce Paltrow, was equally as devastated the duo's relationship came to an end. "My father was devastated," she said 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." She added: "I didn't know what I was doing."

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Shortly after walking away from Pitt, Paltrow entered a three year on-and-off relationship with Ben Affleck in 1997, but her experience with the 'Argo' director didn't seem as positive. "He was not in a good place in his life to have a girlfriend," she said of the now 42-year-old.

Affleck wasnt in "a good place" during his relationship with Paltrow

"I think that when you're in your twenties, you can get swept up in [good looks]," she noted of being continued. "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."

Furthermore, Paltrow's parents weren't Affleck's biggest fans either. "I think they appreciated how he's super intelligent and he's really talented and funny," she said of her dad and actress mom Blythe Danner. "They loved him, but they were okay with us not being together."