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Ben Affleck was already accustomed to the attention that came with celebrity relationships before dating Jennifer Lopez. He thought his previous romance with Gwyneth Paltrow primed him for what he had to face as Lopez’s boyfriend. But much to his disappointment, Affleck discovered that this wasn’t the case.

Ben Affleck thought his celebrity relationship with Jennifer Lopez couldn’t have been any worse than with Gwyneth Paltrow

Ben Affleck posing at the 18th Annual Hollywood Film Awards.
Ben Affleck | Axelle/Bauer-Griffin/FilmMagic

Paltrow and Affleck briefly dated each other after co-starring in the Oscar-winning feature Shakespeare in Love. The two were both already well-known in the film industry at the time, which meant their relationship drew much attention. So when Affleck moved on and later found himself dating Lopez, he figured he knew what to expect.

“I’d been through it before with Gwyneth, and I thought, how bad could it get, how much could they do? Well … I found the answer to that question. And … I wasn’t really prepared,” Affleck once told SF Gate.

Affleck and Lopez discovered that the focus on their celebrity relationship was much more intense than either would’ve guessed. Unlike with his relationship with Paltrow, Affleck had to alter his entire lifestyle around while dating Lopez.

“In the last four or five months, we’ve made a lot of changes, and it unfortunately comes down to: I do hide in the backseat of a car. I do try to elude people as best I can. I try not to end up being in any pictures at all that I don’t want to be in,” Affleck recalled.

In an interview with The Gainesville Sun, Affleck remarked that his strategy was simply to wait until tabloids moved onto another couple.

“Then there’s somebody else – like Colin Farrell’s dating Britney Spears – and you’re off the hook,” he said.

Ben Affleck didn’t know what happened between himself and Gwyneth Paltrow

Affleck and Paltrow remained friends despite their break-up, which he attributed to Paltrow’s own warm personality. The two even remained friendly enough to play love interests in Bounce without issue.

“Fortunately, Gwyneth is very mature. She’s not a vindictive person, and she’s not bitter or spiteful. She’s just got enormous depth of spirit and soul. Most people do not quite have the grace of spirit that she does,” Affleck once said according to The Free Library.

But at the same time, when asked about what caused his and Paltrow’s split, Affleck wasn’t sure himself.

“I don’t know what went wrong between us,” Affleck said. “I really don’t. Friendship is the basis of a good relationship… But I can’t really answer that. It’s just too complicated and too personal – and she’d kill me if I said any more.”

Paltrow theorized that Affleck simply wasn’t ready for a true relationship at the time. Which was why her parents had no qualms about Paltrow and Affleck breaking up.

“I think [my parents] appreciated how he’s super intelligent and he’s really talented and funny, but he wasn’t in a good place in his life to have a girlfriend. They loved him, but they were OK with us not being together,” Paltrow once said on The Howard Stern Show (via Marie Claire).

Gwyneth Paltrow wasn’t surprised to hear about Ben Affleck’s troubles with Jennifer Lopez

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Affleck’s first relationship with Lopez was met with a variety of problems that eventually resulted in their engagement being called off. Paltrow confided that she wasn’t the least bit surprised with the development given what she knew about Affleck.

“Ben makes life tough for himself,” Paltrow once told ABC News. “He’s got a lot of complication, and you know, he really is a great guy. So I hope he sorts himself out.”