Katie Cleary considers herself a model, actress, philanthropist, and filmmaker, and spends much of her time helping improve animal welfare. It seems that the philanthropist part might not be so accurate, as it literally means “lover of people.” Apparently, the celebrity was caught getting herself all nice and cozy with Leonardo DiCaprio at the Cannes 2014 festival while she was still married to her then-husband, Andrew Stern. It has been rumored that she also had some fun with “Entourage” star Adrian Grenier at that same event. This and probably many other events resulted in her husband, Stern, committing suicide mere weeks after the event.
Cleary ended up receiving exactly nothing in inheritance from her husband’s estate, which all went to her late husband’s parents. Katie runs an animal charity, and the two (Leo and Katie) probably got together over their shared passion for the environment and animal rights. Still, perhaps it would have been better to also think of the rights and needs of those closest to her. After the whole tragedy had run its course, the actress continued her life as usual and is currently working as a Netflix producer. Clearly also founded World Animals News, a website that shares all the latest in animal updates worldwide.
Alesia Riabenkova
When you date a lot of women, especially those who come from the glamorized entertainment industry of Hollywood acting and modeling, you're bound to stumble on some wacky women. Alesia Riabenkova may not be crazy, but she certainly has a lot of drama surrounding her. This ex of Leonardo Dicaprio was also the girlfriend of Gerard Butler at one time.
Alesia Riabenkova has been involved in some controversy over the years. It's a good thing DiCaprio dated her before allegations ever emerged, as he has been quite clear of any controversy despite dating so many women. The Latvian-born model will probably not see a lot of work from Hollywood in the coming years, mostly because fashion companies tend to stay away from women who are considered "troubled." It’s not a surprise then that the DiCaprio-Riabenkova relationship was nothing but a short blip on the iconic actor’s romantic resume.
Toni Garrn
Right after his problematic relationship with Alesia Riabenkova, DiCaprio moved on to date Toni Garrn, the German-born Calvin Klein model, Hollywood actress, and self-titled humanitarian. Garrn worked with both Calvin Klein and Victoria's Secret and even acted in a couple of films. She became an ambassador for Plan International's global "Because I am a Girl" campaign, whose goal is to help eliminate gender inequality worldwide. She also founded the Toni Garrn Foundation, which seeks to help women's rights and advocate for gender equality.
DiCaprio and Garrn dated on and off through 2013 and 2014. Perhaps this was the actor's way of filling the void left by his former girlfriend, Bar Refaeli, who happens to look very similar to Garrn. Leo and Toni didn't quite manage to make things stick and left the on-and-off relationship, which lasted for about a year. In a stunning turn of events, Leo was seen in 2017 walking hand in hand again with Garrn, as the two presumably got back together for a short time before splitting up again. You can really tell the look of pride on Toni Garrn's face as she took the bachelor out for a walk. She was grinning from side to side while he held his head down in shame. The model has over 1.5 million Instagram followers, and it seems her modeling career will only get better for her from now on.
Demi Moore
Young Demi Moore was considered one of the hotties of Hollywood back in the '80s and married stars such as Freddy Moore, Bruce Willis, and even Ashton Kutcher. All of the successful actresses' marriages dissolved after 3 to 6 years, and DiCaprio just happened to be somewhere in between Willis and Kutcher. The then-young actor met with Demi Moore for a few late-night dates, and in a picture that looks like something from a movie scene (it was captured just after the actress finished filming “G.I. Jane” where she shaved her hair), DiCaprio was clearly looking a bit uncomfortable and perhaps even in pain, as he wasn't used to dating women older than him, especially those without long blonde hair.
This cougar didn't manage to catch DiCaprio, and the two dissolved about as quickly as the foams in their late-night lattes. Moore was considered quite a big-time actress in the '80s and '90s and went on to break many records, including being the highest-paid actress in history when she received $12.5 million for her role in the 1996 black comedy "Striptease." She then acted in various films, including "G.I. Jane," "Charlie's Angels: Full Throttle," "Margin Call," and many more, although nothing managed to top her fame from the '90s, which was certainly her best decade. Since then, the actress has focused much of her time on supporting charities and doing work to promote animal rights, and attempting to disrupt child trafficking.
Rihanna
It's been believed that Leonardo DiCaprio had a thing going with Rihanna for a long time. The two were often seen together at clubs, and rumors were starting to emerge that perhaps something was happening behind the scenes. Skeptics thought there was likely too much divide between the two, as they came from very different backgrounds, and Rihanna, being the extremely dominant and power-savvy woman she was, lacked a certain kind of "passiveness" that is often associated with the models and actresses DiCaprio usually dates. After a while, the press discovered that indeed, the two were not dating. Instead, they found out that Rihanna had been linked to one of Leonardo's friends and not the actor himself.
Rihanna dated Drake on and off from 2009 until 2016, although she was also involved at the time with Chris Brown. She welcomed her first child in 2022 with her partner, rapper A$AP Rocky.