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Jennifer Lopez filed for divorce from Ben Affleck in August 2024 following months of speculation that the couple was headed for an official split. Lopez and Ben first fell in love in the early 2000s. While they called off their engagement in 2004, Lopez likely got to know Ben’s younger brother, Casey Affleck, during that time. Recently, Casey’s girlfriend called Lopez “generous and genuine” as the exes undergo the divorce proceedings.

Casey Affleck’s girlfriend, Caylee Cowan, said she ‘hates’ that Jennifer Lopez receives hate

Jennifer Lopez and Ben Affleck appear on OK terms through their divorce proceedings. Lopez stated the date of separation as April 26, 2024, proving they haven’t been together in months. They were spotted out to brunch in September 2024, with some sources claiming they were packing on the PDA despite their status as a soon-to-be-divorced couple.

Casey Affleck knows Lopez quite well. She and Ben initially began dating in the early 2000s before ending their engagement in 2004. While Ben went on to marry Jennifer Garner in 2005, Casey has never uttered any poor words publicly regarding Ben and Lopez. When Lopez and Ben tied the knot in 2022, he joked on Instagram that Lopez should prepare for “dysfunction.”

“Welcome to the family,” Casey wrote. “Get ready for some real dysfunction! Kidding. I am kidding. … Jen, you are a gem. We love you so much!!!”

Casey’s girlfriend, Caylee Cowan, whom he’s been dating since 2021, had kind words to say about Lopez while speaking to DailyMail.com. Cowan called Lopez one of the “nicest, sweetest people ever.”

“I love her so much,” Cowan said. “I love Jen. Jen is a very generous and genuine person. I hate that she gets so much hate because she’s genuinely one of the nicest, sweetest people ever.”

Cowan added that Lopez sends her flowers for her and Casey’s birthdays. “She’s a thoughtful person,” she continued.

A source once claimed that Casey Affleck thought his brother’s second marriage was ‘superficial’

Ben Affleck, Jennifer Lopez, and Casey Affleck walking down the street together in 2002
Ben Affleck, Jennifer Lopez, and Casey Affleck in 2002 | Bauer-Griffin/GC Images
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Casey Affleck has never publicly indicated that he dislikes Jennifer Lopez. However, a source told OK! Magazine in 2022 that Casey thought Ben Affleck and Lopez felt “superficial” as a couple.

“He finds them superficial,” the insider alleged. “Ben and Jen are at the center of the whole L.A. social scene, which Casey finds frivolous and has really divorced himself from.”

The insider added that Casey isn’t interested in attaining the levels of fame that Ben and Lopez mastered. “The fancy parts of being famous hold no interest to him,” the source continued, making him much different from his brother.

“Casey is allergic to the circus Ben’s life has become, and it’s just not a world he knows or cares to navigate,” the insider added. “He and Caylee won’t be double-dating with Bennifer anytime soon!”

Jennifer Garner, Matt Damon, and Ben Affleck’s family are allegedly helping Ben get through the divorce

Ben Affleck doesn’t have to go through his divorce from Jennifer Lopez without support. A source told In Touch Weekly that Ben’s family and friends—including Casey Affleck, Jennifer Garner, and Matt Damon—are watching him closely, as they worry he may drink to deal with the split. The source called the group Ben’s “mercy squad.”

“That’s the main reason you’re seeing Jen going over there nearly every day to make sure he’s OK,” the source explained. “His mother, his brother, and his close friends, like Matt Damon, are helping out too.”

The insider added that Garner, Damon, and Ben’s family are acting as “a team” of support. “If they’re seeing a thing to worry about, they alert each other immediately,” the insider continued. “Ben knows they’re all in touch, but he doesn’t know the extent of it.”

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