Kick Kennedy wasn’t ‘thrilled’ when Ben Affleck quarantined with Ana de Armas in 2020, report says

Ben Affleck’s spokesperson isn’t have much luck quieting reports that the actor is “spending time” with Kathleen “Kick” Kennedy, a member of the Kennedy family and the daughter of polarizing former presidential candidate Robert F. Kennedy Jr.

Even after the spokesperson issued a statement to People saying that Affleck, 52, and Kennedy, 36, are not dating and “I don’t know if they even know each other,” stories continue to pour forth about the “Argo” star and his alleged special connection to Kennedy. Multiple outlets have reported that Affleck and Kennedy, a sometime actor, have been hanging out at different Hollywood hotspots amid in his divorce from Jennifer Lopez.

ARLINGTON, VA – JUNE 06: Kick Kennedy, daugther of Robert F. Kennedy Jr. and grandaughter of Robert F. Kennedy attends a Remembrance and Celebration of the Life & Enduring Legacy of Robert F. Kennedy event at Arlington National Cemetery on June 6, 2018 in Arlington, Virginia. (Photo by Leigh Vogel/Getty Images for RFK Human Rights ) 

On Tuesday, Page Six added some more context to Affleck and Kennedy’s alleged bond by reporting that their “friendship” goes back a few years, to before he began to date “Blonde” actor Ana de Armas in March 2020.

“Their friendship has been going on for a while, even before Ana,” one Hollywood insider told Page Six. The Daily Mail reported Monday that the Boston-reared Affleck was drawn to Kennedy because, as a source said, “when you live in Boston, the Kennedy family is royalty.” The source said “he legit thought he had landed into the Kennedy family” when he started “hanging out with Kick.”

This image released by 20th Century Studios shows Ben Affleck, left, and Ana de Armas in a scene from “Deep Water.” (Claire Folger/20th Century Studios via AP) Claire Folger/20th Century Studios via AP

The Daily Mail even reported that Affleck and Kennedy “had a brief fling” but that the relationship didn’t last because “she was too young and not ready for anything serious.”

It’s not known if Affleck himself was ready for anything serious at the time. He finalized his divorce from his first wife Jennifer Garner in 2018. Amid that divorce, Affleck went into rehab for his on-off struggles with alcohol addiction, but he also dove into a brief fling with a 22-year-old Playboy Playmate model, Shauna Sexton. A few months later, in early 2019, he broke up a second time with “Saturday Night Live” producer Lindsay Shookus, after more than a year of dating.

In between Garner, Shookus and the Playboy Playmate, it’s not known when Kennedy crossed paths with Kennedy. But by early 2020, he had begun seeing de Armas, after meeting the Cuban-Spanish actor on the set of their sexual thriller, “Deep Water.” With the onset of the COVID-19 pandemic in March 2020, Affleck and de Armas chose to quarantine together.

“Kick was less than thrilled” about Affleck’s quarantine companion, a source told Page Six.

By January 2021, Affleck’s relationship with de Armas was over, and he soon reconnected with Lopez, with whom he had enjoyed a high-profile three year romance in the early 2000s. They became engaged but they called off their 2003 wedding and broke up in 2004, citing the pressure of intense media scrutiny.

TOPSHOT – US actress/singer Jennifer Lopez and US actor Ben Affleck arrive for the premiere of “The Mother” at the Westwood Regency Village Theater in Los Angeles, California, on May 10, 2023. (Photo by Michael Tran / AFP) (Photo by MICHAEL TRAN/AFP via Getty Images) 

Affleck, Lopez and the world was enthralled when they rekindled their romance in 2021, with Lopez reportedly believing in the “fairy tale” idea that she had finally connected with her great love and that they were both older, wiser and ready to commit to make their love last. They married in a lavish August 2022 wedding.

But Lopez was wrong about the fairy tale. Affleck reportedly came to see their relationship as “a fever dream,” while his “extreme” mood swings drove a wedge between them and created “a toxicity” in their relationship that was “pervasive,” both Page Six and People reported. He, meanwhile, was open about not liking the way she always seemed to need the spotlight and to share her private life on social media.

Lopez filed for divorce last week, citing irreconcilable differences and revealing that she and Affleck officially separated in late April. While he moved out of their $68 million Beverly Hills mansion, and she canceled her summer concert tour and enjoyed an extended vacation in Europe and the Hamptons, he reportedly began spending time with Kennedy in Los Angeles.

Page Six reported that Affleck and Kennedy have been spotted together at the Polo Lounge at the Beverly Hills Hotel over the past few months. A source told the Daily Mail tried to make it clear that they didn’t begin seeing each other until after Affleck and Lopez had separated.

But Kennedy isn’t saying too much, the Daily Mail said. The granddaughter of Robert F. Kennedy and great-niece of John F. Kennedy knows how to keep secrets and has remained tight-lipped about Affleck because she doesn’t want to be seen as “a mistress,” the Daily Mail source said. Also, unlike the famously attention-seeking Lopez, she “likes to keep her private life private,” the source added.

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