Leonardo DiCaprio first caught the public’s eye as Tobias in the 1993 film “This Boy’s Life.” That role opened the floodgates to a slew of acting opportunities, captivating audiences everywhere with his California charm. However, it’s not just his performances on screen that have drawn attention. Leonardo’s tumultuous dating life and his pattern of short-lived relationships have sparked discussions for decades, earning him a reputation as a quintessential example of problematic dating habits.
We’re delving into why he seems to cycle through models at a breakneck pace, why his relationships often end when his partners reach a specific age, and his notorious aversion to long-term commitment, reminiscent of his role in “Catch Me If You Can.” Are you finding that your hotel room seems to be a temporary haven for the newest it-girl in town? Take what you read with a grain of salt. We’ll also shed light on his supposed ties to Hollywood’s infamous “P Posse”—and let’s just say the “P” stands for exactly what you think.
To truly understand a person’s present, we often need to look at their past. Let’s travel back to the 1940s. Ermelin Indenbirken was born in a German air raid shelter. She spent the first two years of her life in a hospital, first recovering from a broken leg and then fighting multiple infections and chronic malnutrition. When she was 11, her family immigrated to the U.S. and settled in an apartment in Brooklyn. It was here, while attending a city college, that she met George DiCaprio.
After getting married, they moved to Los Angeles, dreaming of endless job opportunities. Instead, they found themselves making low salaries and struggling to get by. Ermelin got pregnant in 1974, and they managed to save enough for a babymoon in Florence, Italy. During their visit to the Uffizi Gallery, Ermelin was captivated by a Leonardo da Vinci painting. Feeling her baby kick while admiring the artwork, she decided to name him Leonardo. Leonardo DiCaprio was born on November 11, 1974. For those into astrology, he’s a Scorpio with Libra rising.
When Leonardo was still a toddler, his parents divorced but rented adjacent bungalows in East L.A. so they could raise him together. His parents were described as easy-going, liberal, laid-back hippies. Leonardo often looked at his mom’s childhood photos. He once shared that he kept a picture of her with a distended belly full of worms, and imagining what she went through always brought tears to his eyes.
Leo described his neighborhood growing up as pretty rough, with street workers and substance dealers on every corner. As a kid, he saw people engaging in same-gender intimate acts in broad daylight and watched addicts using drugs in back alleys. He got a scholarship to a private school in Westwood, which was his first glimpse into the lives of the upper class. He made friends with kids from Beverly Hills and got to play basketball in their huge backyards. But eventually, he had to go back to public school, where he was beaten up on his first day back.
Leo had done a bit of acting before, but after that first day back, he decided to pursue it seriously. He wanted to get out of the public school system and earn enough money to help his family live in better conditions. His parents let him drop out of high school after his junior year, and he joined a local drama center to perfect his acting skills. That risky decision paid off.
After his role in the 1997 film “Titanic,” Leo became one of Hollywood’s biggest stars. But the constant attention from photographers and the media digging into his private life wore him down. He told the New York Times he decided to protect his privacy by keeping most people at a distance, sticking with a close-knit group of friends, including childhood friend Tobey Maguire and magician David Blaine. There were rumors that their group, known as the “P Posse,” was often seen chasing women at Manhattan nightclubs. One tabloid even speculated that Leo and Tobey might be more than just friends.
The gossip magazine brazenly reached out to Tobey’s mom, saying they were working on an article about gay celebrities in Hollywood. They slyly asked if she wanted to share any thoughts about Tobey’s close friendship with Leo. Tobey’s mom took the bait and told them, “Those two are just free-spirited guys. Most of their friends are gay, and they’re comfortable with that. I think Leo and Tobey bridge the gap between men and women, accepting their feminine traits.”
As we know, Tobey left the single life briefly in 2007 when he married Jennifer Meyer, while Leo remained unattached and always on the lookout. Leo has been nominated for several Oscars and finally won his first in 2016 for “The Revenant,” bringing his mom as his date. When he’s not in a relationship, his mom often accompanies him to red carpet events. According to online sources, he loves giving her the star treatment, and she enjoys getting all glammed up for his high-profile occasions. She’s become a constant presence in his life, and insiders say that any woman wanting to get close to Leo has to win over his mom first.
Initially, no one questioned Leo’s dating life since his girlfriends and alleged flings were all around his age. There was Bridget, Naomi, Kristen, Helena, Bijou, Amber, Eva, Gisele, Bar, Madalina, Erin, and Toni—all supermodels. But what did Leo have in common with these women? Not much. According to a writer for The Guardian, he started dating Gisele Bündchen around 2000. During a 2001 interview with the supermodel at Leonardo’s house, Gisele was described as volatile and entitled, while Leo came off as withdrawn and very quiet
Their differences reportedly led to their 2005 breakup. Gisele told Porter magazine, “No longer numbing myself with smoking, drinking, and too much work, I was becoming more and more aware of things that I’d chosen not to look at.” While she was doing some serious soul-searching, Leo wasn’t ready to embrace her new lifestyle. So, after a five-year, on-again, off-again relationship, 25-year-old Gisele and 30-year-old Leo went their separate ways. He later admitted that he rarely felt strong emotions, had never been in love, and didn’t believe in marriage.
But in 2008, while dating supermodel Bar Refaeli, Leo seemed to have a change of heart. He told Parade Magazine he was ready to settle down and have children. He shared with The Guardian that he wanted an independent wife who wouldn’t mind if he spontaneously went off to Alaska with his friends. He also told CBS This Morning he liked a woman with humility, a sense of humor, and not a lot of drama. Was Bar the one? Absolutely not. They broke up in May 2011 after five years together. Interestingly, Bar was also 25 at the time of their split, while Leo was 36.
Just days after their breakup, Leo was spotted getting cozy with “Gossip Girl” star Blake Lively on a yacht. E! News speculated that 24-year-old Blake might be the one to tame the wild bachelor, but their relationship fizzled out after five months. What went wrong this time? Reportedly, it was his mom, Ermelin. A source told an online site that Blake didn’t get along with Leo’s mother. The insider added, “His mom told Leo that Blake was far too up herself for him. Leo listens to his mom, and the fact she didn’t like Blake put him off.”
Just days after ending things with Blake, he was linked to 21-year-old Australian model Alice Crawford. One of Alice’s friends told the Daily Mail, “He texts her when he wants to see her, and they hook up a few times a week. They’ve mostly been meeting up during the week. He does other things on weekends.” Unsurprisingly, that situation didn’t last long either, and by December 2011, he was spotted with 22-year-old Victoria’s Secret model Erin Heatherton. After about 10 months of dating, Leo reportedly dumped her. Cosmopolitan magazine noted that Erin was Leo’s 23rd supermodel ex-girlfriend. Yes, 23rd.
Leo attempted to explain his numerous breakups to Esquire magazine, saying it was difficult to maintain relationships while constantly traveling and filming on location. He added that he didn’t even have time to take care of his dog, so he had to give it to his mom. Over the years, Leo has been linked to several women, including Rihanna. They were spotted partying together at the Playboy Mansion in January 2015, with one partygoer tweeting, “Just saw Leo and Rihanna make out while ‘Pour It Up’ was playing. What is life?” However, that fling ended quickly, and later that same year, many believed Leo had finally found “the one” in model Kelly Rohrbach. After four months of dating, he proposed to the 25-year-old supermodel in October 2015, and a source told OK! magazine that Leo’s mom loved and approved of her.
But what could go wrong? In true Leo fashion, his heart didn’t stay committed, and he ended things three months after the engagement news. By then, people were trying to figure out what was going on with Leo. Lisa Arcella, who wrote a book about Leo’s life, told the Daily Mail that his mother might be the reason Leo struggled to find true love. She revealed that due to his upbringing and the sacrifices his mom made for him, Leo felt indebted to her and put her on a pedestal. While he spoiled his mom and gave her the life he felt she deserved, it made it hard for him to give his romantic partners the attention they needed. It seemed like Leo might be a bit of a mama’s boy, which isn’t always a bad thing. According to Verywell Mind, research shows that men who have strong relationships with their mothers are mentally healthier, more empathetic, and have better relationships with women. However, it’s essential for the partner to set clear boundaries, especially if the mom tends to interfere in her son’s relationships.
Leo’s next serious relationship began in 2017 with model Camila Morrone. A year later, a source told Us Weekly they wouldn’t be surprised if Leo proposed to her over the holidays, but a proposal never happened. She accompanied him to the Cannes Film Festival, but according to Vice, he didn’t introduce her as his girlfriend to the press or walk the red carpet with her. In August 2022, Leo and 25-year-old Camila broke up.
If you’ve noticed a pattern, his relationships often end when his girlfriends turn 25. Many people have speculated that he does this intentionally. According to Page Six, an insider claimed that by the time his girlfriends approach 25, they start talking about marriage and having children. Although Leo has publicly stated he wants these things, deep down, he’s still sowing his wild oats. Allegedly, the insider added, “He does not want a family and does not want to be around women who may press him for that.” So, it seems like Leo has changed his mind about settling down, which is fine. But is he being upfront with the women he dates? We’re unsure. The source also mentioned that once a woman meets Leo, the clock starts ticking. If she gets too old, she’s out the door. If she gets too close, she’s gone. His preferred age range for companionship appears to be between 21 and 25, and some people even applaud him for keeping a young woman on his arm. As of September 2022, 47-year-old Leo has been linked to model Gigi Hadid, who is 27 and a mother. It seems Leo might be breaking his own rules with this romance, but will it last? We’ll have to wait and see.