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Tobey Maguire. Much like DiCaprio, the Spider-Man star is notorious for dating women much younger women and the newest addition to his list is 20-year-old model, Lily Chee. The actor, 49, was seen ...
12 hours ago · Leonardo DiCaprio is notorious for only dating women younger than 25 years old. ... While memes about Leonardo DiCaprio and his fixation over 20-year-old women keep rolling out, many have found ...
- Kate Ng
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- Bridget Hall, 1994. DiCaprio (20 at the time) and US model Bridget Hall (then 17) dated at the start of his Hollywood movie career. However, the pair’s relationship has been described as a “fling” and lasted only a brief period of time.
- Naomi Campbell, 1995. Naomi Campbell attends the 68th Academy Awards, held at the Dorothy Chandler Pavilion in Los Angeles, California, 25th March 1996. (Getty Images)
- Kristen Zang, 1995-1999. Kristen Zang dated DiCaprio on-and-off for four years when they were both in their early 20s. She wrote an essay for People magazine last year, in which she called out “ageist” headlines about his split from Camila Morrone.
- Helena Christensen, 1997. Following his extraordinary success with the 1997 classic Titanic, DiCaprio (early twenties) was spotted partying with Danish model Helena Christensen (29 at the time) on a number of occasions.
- Bridget Hall (1994) Leo had his first public relationship with supermodel Bridget Hall. The two were spotted canoodling in 1994 when they were just teens, though neither ever confirmed the relationship.
- Naomi Campbell (1995) Naomi Campbell is arguably the biggest name on the list of models Leo dated in the ‘90s. Their relationship, however, was as fabled as it was brief.
- Kristen Zang (1996 to 1997) A year after breaking up with Naomi, Leo started seeing actress and model Kristen Zang. The two were madly in love and had a lot of common friends, like one big happy family.
- Amber Valletta (1997) In the colourful saga of Leonardo DiCaprio’s dating history, the chapter on Amber Valletta unfolds in three parts: Leo glimpsed Amber in a magazine, was immediately smitten, and a brief affair followed.
- Gavin Rossdale. After his marriage to Gwen Stefani, Gavin Rossdale has only been linked to women around half his age. In 2017, he was dating Sophia Thomalla, an actress who was 27 when they got together (and he was 51 years old).
- James Marsden. In late Oct 2023, James Marsden was seen smooching a 25-year-old model named Frederique Brons, which happened after his breakup from singer Edei, who was 25 years his junior.
- P. Diddy. Sean ‘Diddy’ Combs began dating singer Cassie when she was just 19 while he was 36. She has since accused him of physically and sexually abusing her throughout their 10 year relationship.
- David Schwimmer. While David Schwimmer has normally dated people younger than him, his two relationships that have raised the most eyebrows was with Zoe Buckman, who’s 19 years his junior, and Tina Barrett, who’s 10 years his junior.
Sep 26, 2022 · Leonardo DiCaprio reportedly dated co-star Brittany Daniel briefly in 1994, according to The Sun. They met while filming 1995's "The Basketball Diaries." Brittany starred alongside her real...
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Jun 29, 2023 · The actor is believed to have recently split from his girlfriend of five years, actor Camila Morrone, but has previously been romantically linked to the likes of Blake Lively, Naomi Campbell...
