Kick Kennedy Was ‘Less Than Thrilled’ When Ben Affleck Started Dating Ana de Armas, Source Says

Ben Affleck and Kathleen 'Kick' Kennedy go way back. Here's what an insider alleged regarding how Kennedy felt when Affleck started dating Ana de Armas in 2020.

Jennifer Lopez and Ben Affleck are officially divorcing in 2024 after two years of marriage. The couple first fell in love in the early 2000s and got back together nearly 20 years later before tying the knot in 2022. Now that Lopez and Affleck are done, several reports suggest Affleck is trying a romance with Robert F. Kennedy Jr.’s daughter, Kathleen “Kick” Kennedy. Here’s what an insider alleged regarding when Affleck and Kennedy first started their fling in 2020.

Kick Kennedy was allegedly upset when Ben Affleck started dating Ana de Armas in 2020

Ben Affleck and Kathleen “Kick” Kennedy are getting more attention than ever as Jennifer Lopez and Affleck move through their divorce. Lopez filed for divorce from Affleck on Aug. 20, 2024. The papers noted that the couple officially separated in April 2024. Shortly after the filing, Affleck was spotted with Kennedy, causing rumors to fly.

While Affleck’s representatives attempted to shut down dating rumors, fans can’t ignore the actor and the politician’s daughter’s past. Affleck and Kennedy were first linked in early 2020, well before Affleck and Lopez rekindled their romance. Unfortunately for Kennedy, Affleck fell for actor Ana de Armas in March 2020. Affleck and de Armas initially met on the set of Deep Water in 2019.

“Their friendship has been going on for a while, even before Ana,” an insider alleged to Page Six. “When Ben started seeing Ana in 2020 and chose to quarantine with her during COVID, Kick was less than thrilled.”

A rep for Affleck told Page Six that Kennedy and the actor aren’t hanging out. However, another source told the publication that Affleck “would love nothing more than to be part of the Kennedy clan. It’s a dream for any Boston guy. … I think he would rather have that than a billion-dollar, red-carpet glam life with J.Lo.”

An eyewitness said Ben Affleck and Ana de Armas were ‘kissing’ and ‘cuddling up’ in March 2020

Ben Affleck and Ana de Armas didn’t have a long-lasting romance. The actors dated from March 2020 to January 2021. However, according to sources who saw the couple, their passion seemed to burn bright.

“They are without a doubt a couple,” an eyewitness told E! News in March 2020. “They have been kissing, cuddling up together, and putting their arms around each other a lot. They look at each other adoringly and like taking pictures of each other. Ben seems blissfully happy and giddy. He can’t stop smiling and laughing. He is clearly is very into Ana.”

So, why did Affleck and de Armas break up? A source told People that de Armas no longer wanted to be in Los Angeles, but Affleck hoped to stay there for his three kids.

“She broke it off,” the source claimed. “Their relationship was complicated. Ana doesn’t want to be Los Angeles based, and Ben obviously has to since his kids live in Los Angeles.”

The ‘Argo’ actor is allegedly pausing his romance with Kick Kennedy

Sources told DailyMail.com that Ben Affleck is pumping the breaks on his relationship with Kick Kennedy in 2024. The actor is allegedly concerned that the romance could affect his divorce from Jennifer Lopez.

“He is trying to pull the ‘I don’t know her’ card, but what he failed to realize is that they weren’t the only two people in the world that knew that they used to hook up, or that they were hanging out again,” a source claimed. “He fears that this will affect his divorce, and even though there was no overlap, saying he didn’t even know her was not the right move.”

As for Kennedy, she allegedly thinks of Affleck as “intelligent,” but she “does not want to be seen as a mistress.”

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