Jennifer Flavin, Sylvester Stallone’s First Date – Hollywood Life

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The central storyline of the May 31 episode of The Family Stallone revolved around Scarlet Stallone‘s breakup with her on-again/off-again boyfriend, Joe. And while that was somewhat upsetting — Scarlet was initially sad, but quickly got over it — it inspired family matriarch Jennifer Flavin to look back at her 35-year relationship with Sylvester Stallone.

Since Sly was away in Atlantic City with his brother, Frank Stallone, Jennifer invited her longtime best friend, Kirstin, over for a chat at the family’s Los Angeles house. And after mentioning that Scarlet had just experienced an upsetting heartbreak, Jennifer started reminiscing about the night she met Sly and how Kirstin was right by her side. Jennifer said she and Sly met at a restaurant, and in his private confessional, Sly said he also “vividly” remembers the night he met her.

“It was in this dark restaurant with a few people. She came in and — something happened,” he said, while back in her conversation with Jennifer, Kirstin added,  “I’ll never forget seeing his face, when he saw you for the first time. I witnessed it.”

“I just felt like this jolt. [I wondered], ‘Did we just have a minor earthquake or something?’,” Sly further admitted in his confessional.

Jennifer said they “just hit it off. It was crazy, like we were inseparable all night.” After meeting at the restaurant, they went to a club downtown, but she refused to join him in his limousine. Instead, she and Kirstin followed Sly in their Dodge Duster, which was “parked out back.”

Sly said he looks back on that time fondly, and now, he’s very happy that they met. “Things happen when you least expect it. Nobody knows what life is going to bring. And then 35 years later, you look at your beautiful family and you realize you’re the luckiest son of a b**** in the world,” he said. Back at the house, Kirstin laughed, and told Jennifer that she and Sly have “been through a lot” since their first date, and Jennifer agreed.

But this moment, of course, was filmed shortly before Jennifer and Sly separated after 25 years of marriage in Aug. 2022. He even removed tattoos dedicated to her. Fortunately, they called off their split in Sept. 2022, one month after she filed court docs, and in early October, they officially cancelled their divorce, according to Page Six. Considering how special their meet cute sounds, we’re happy they found their way back to each other.

Want more? New episodes of The Family Stallone drop on Paramount+ every Wednesday at 3am ET.

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