Sylvester Stallone Felt 'Trashed' after 2 Failed Marriages — He Once Made 3rd Wife Cry a Lot by Dumping Her

Action movie star Sylvester Stallone has been married three times. He said his first two marriages broke him even though he was a serial cheater and confirmed it himself.

After two failed marriages, actor Sylvester Stallone expressed that he felt "battered," "scarred," "trashed," and "humiliated," but he later found love in his third marriage to Jennifer Flavin.

Stallone first met the former American model at a West Hollywood restaurant in 1988. Flavin was 19 years old then and was visiting Hollywood with a friend.

Meanwhile, the New York native was an established Hollywood star with a bad reputation regarding his love life. By 1984, Stallone had wrecked his 10-year marriage to his first wife, Sasha Czack.

The former couple had tied the knot in 1974 and divorced in 1985. The pair welcomed two children together, sons Sage and Seargeoh.

Stallone later remarried Danish actress Brigitte Nielsen in 1985, but the union ended in 1987 after 19 months. He revealed that the divorce left him reeling.

STALLONE & FLAVIN'S RELATIONSHIP WAS FAR FROM ORTHODOX

But all that changed when he met Flavin, whom he spent time with at his homes in Benedict Canyon and Malibu. Flavin told People in May 1994 that she would come over and she and Stallone would watch a movie, cook dinner, and take walks on the beach.

Stallone would also drive to the San Fernando Valley to spend time with the California native at her family home. He found that kind of life meaningful, telling the Toronto Star three years into their relationship:

"I'm loving life again. Jennifer has made all the difference."

However, the couple's romance was far from orthodox. Stallone revealed in 1991 that they were more or less single when they were apart: "When we come together, it is wonderful. When we are separate, there are no strings attached. That's the way it is. No strings."

Meanwhile, Flavin knew what he meant by that and shared in 1992 that she was aware of her boyfriend's behavior when not next to her, saying:

"I'm not naïve about what may go on when I'm not around – he's a 45-year-old man – and I can't change the way he is. Still, he's not a cheating dog every day of the week."

Flavin explained that she and the "Rocky" star spent five out of seven nights together, so there would be a less likely chance for him to cheat daily.

But that was far from it because he managed to be unfaithful regardless of how often they were together. Flavin's loved ones revealed that they could not fathom her level of gullibility when it came to Stallone.

Her mother, Shirley, disclosed that she always wanted to trust her lover no matter what. Flavin's long-time friend, Kirstin Wolf, added that her pal was the kind of person who always wanted to "believe in the best in everyone" and would state that Stallone loved her, so his cheating ways were never an issue.

But Flavin admitted to being overly susceptible to her partner's claims of innocence. The business owner revealed that she used to hear things about Stallone. Still, he always managed to redirect the situation, telling her that it was just a woman with whom he took a picture or that people would always talk about him as a famous individual.

SUDDEN BREAK-UP

While Flavin believed that everything between her and Stallone was on good grounds, things abruptly changed. One day he unexpectedly broke up with her via a six-page handwritten letter in pen, delivered through Federal Express, a move she described as "sloppy."

Stallone had ended their nearly six-year relationship, and she learned the reason why from her agent. It turned out that the filmmaker had been having an affair with another woman named Janice Dickinson, a model.

In addition, it had been widely reported that Stallone had impregnated Dickinson, who had given birth to a daughter named Savannah Rodin. Before dating Stallone, she had ended things with film producer Michael Birnbaum after admitting that she cheated on him with the screenwriter.

The news shocked Flavin, who expressed emotional turmoil resulting in being blind-sided by Stallone. The pair had initially discussed having children and had picked out names:

"It hit me like a ton of bricks. I had no idea this was going to happen. We talked about us having children, about when I was going to get pregnant. We were already picking names, marking down names that he liked and I liked."

The entrepreneur revealed that she had no idea how Stallone and Dickinson became involved. Interestingly, the two women previously worked together and even became social at some point. Two years before the bombshell, Flavin and Stallone had bumped into Dickinson at Planet Hollywood in Manhattan and conversed.

She admitted to enjoying their small talk while adding that she never knew they would reconnect later. Flavin divulged that she "cried a lot" after everything came out in the open. She called all her friends and cleaned her apartment more than once daily.

The stunner shared she had many photos and belongings to get rid of, adding what crushed her the most was how Stallone broke up with her.

Flavin said she was disappointed because that was not the way to end a relationship after so many years. She noted that she would not have begged him to stay but would have appreciated the courtesy to have had at least a conversation about it.

Flavin stated that she was not bitter about their split, while everyone around her suggested she should show anger about how everything panned out. Instead, she dusted herself off and carried on with her life.

The brunette beauty admitted that although the experience was hurtful, she learned from it; hence she picked up the pieces and moved on.

During that period, Stallone stood by Dickinson, believing they had a child together. He even helped her get back in shape only a month after giving birth by providing her with an exercise and vitamin regime. Soon, Dickinson was back at work, and the pair got engaged for six months.

Deep down, Stallone suspected that Savannah was not his daughter and had a paternity test done. On the day of his fiancée's big fashion show, his suspicions were put to rest. Savannah was indeed not his child.

He left the event while Dickinson was still on the runway and when she noticed that he was nowhere to be seen, she went to look for him at a hotel and found him in a foul mood. She recalled his statement at that moment:

"She's not mine. I just heard from the DNA lab in Long Beach. Savannah’s not mine. Send my regards to Mr. Birnbaum – and with that, he stood up."

Stallone was disappointed to learn that Savannah was not his daughter, whom Dickinson said could have been fathered by one of the three men she slept with in a week, including an artist and Birnbaum.

At the same time, he had lost Flavin amid all the trouble. But that was not the end of their love story. Flavin later revealed to People that she and Stallone rekindled their relationship in 1995.

They finally decided to make their relationship official by walking down the aisle in an intimate ceremony held in London's Dorchester Hotel.

STALLONE AND FLAVIN ARE PROUD PARENTS

The couple has since welcomed three children within their marriage, daughters Scarlet, Sistine and Sophia. Their eldest child, Sophia, was born in August 1996 and is an alumni of the University of Southern California.

Sophia currently has makeup and fashion lines, having appeared as a guest judge on the reality TV show competition "Project Runway." She also co-hosts the podcast "UNWAXED" with her little sister, Sistine.

Sistine arrived in June 1998 and has followed in their mother's footsteps by becoming a model. She signed on with IMG Models in 2016.

The youngster also took after her dad and pursued an acting career. Sistine has since made a film debut in "47 Meters Down: Uncaged."

Flavin and Stallone welcomed their youngest daughter, Scarlet, in May 2002, and like her older sister and mom, she is also a model.

The last born also took the plunge by pursuing acting and has so far appeared alongside her father in the 2014 drama film "Reach Me."

In May 2022, Stallone and his beautiful wife celebrated their 25th wedding anniversary. The proud family man commemorated the couple's milestone with a heartfelt post on his Instagram, sharing images of himself and Flavin with a caption that read:

"Happy 25th anniversary to my amazing wife. There are not enough words to describe what this incredibly selfless, dedicated, patient woman has meant to our lives, and I only wish they could be together another 25! Thank you, sweetheart!"

Flavin commented on the sweet post: "Thank you, my love! I love you so much, and we will be spending the next 25+ years together! Keep me laughing, and I'm yours for the rest of my life!"

The mom of three also paid tribute to her husband on social media and thanked him for always making her laugh and for "loving and protecting" their family.