1. Bridget Hall: 17 Years Old

image source: britishvogue.com

It’s believed that model Bridget Hall was DiCaprio’s first ever serious girlfriend, when the pair were seen together back in 1994. Then 17 years old, she attended plenty of events with her actor boyfriend – who would have been 20 at the time. Which actually isn’t so bad a gap based on his later relationships!

2. Naomi Campbell: 25 Years Old

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Supermodel Naomi Campbell and Leonardo DiCaprio were reported to have had a romantic fling in the ‘mid-nineties’ – and the mid-nineties is exactly when Naomi would have been 25 years old. The pair have been lifelong friends, though, ever since their fleeting romance!

3. Amber Valleta: 20 Years Old

image source: usweekly.com

This one is only rumored and we’re not sure when the pair was supposed to have been dating, but as the supermodel’s first marriage was in 1994 and she’s been involved since, we can guess that she maybe dated Leo before 1994 when she was 20 years old. It was rumored he’d seen her picture in a magazine and got into contact with her.

4. Kristen Zang: 22 Years Old

image source: people.com

Model Kristen Zang was Leo’s date to the premiere of the 1996 movie Romeo + Juliet, and she was 22 years old at the time. The pair apparently dated for over 4 years before splitting, and she’s even recently been speaking out about this whole debacle with him, you know… only dating under 25 year olds!

5. Eva Herzigova: 25 Years Old

image source: mizanurrmizan.info

Czech-Italian supermodel Herzigova was 25 years old when she attended the premiere to Leonardo DiCaprio’s movie The Man In The Iron Mask back in 1998 – which is where she allegedly met the actor. It was rumored the pair had a brief two-month romance, but the model has since denied it!

6. Anne Vyalitsyna: 23 Years Old

image source: telva.com

The Russians Sports Illustrated model was believed to be dating DiCaprio when she was 23 years old, after his split from Bar Refaeli. Their relationship was only brief, though, as she went on to marry Adam Levine from Maroon 5, and DiCaprio went on to whichever under-25 model was next.

7. Gisele Bundchen: 18 Years Old

image source: marieclaire.co.uk

Leonardo DiCaprio was 25 years old when he started dating 18-year-old Brazilian model Gisele Bundchen – his youngest girlfriend to date (though that could still change). They actually dated for 5 years, with many public appearances including basketball games and even the Oscars. But it was Gisele who ended the relationship.

8. Bar Refaeli: 20 Years Old

image source: showbizcheatsheet.com

Sports Illustrated model Bar Refaeli was Leo’s next date, and she was 20 years old when she began dating the actor. The pair also lasted around 5 years with an on-off relationship which ended… yep, when she turned 25. But apparently the split was mutual and ‘amicable’.

9. Blake Lively: 23 Years Old

image source: eonline.com

It’s weird to think of Blake Lively with anyone other than Ryan Reynolds, but did you know she dated Leonardo DiCaprio? She was only 23 years old when she dated the actor, while he was 37 years old. It was only a year-long fling where the pair went on many romantic sight-seeing trips together.

10. Erin Heatherton: 22 Years Old

image source: themirror.com

A year later after Lively, Leo started to date Victoria’s Secret Angel Erin Heatherton, who was 22 years old at the time. The pair’s relationship only lasted 10 months before they split, which was apparently because they both had ‘crazy schedules’. Being a famous actor will do that to ya!

11. Toni Garrn: 20 Years Old

image source: harpersbazaar.com

German model Toni started dating DiCaprio when she was just 20 years old, when he was almost twice her age at the time. The pair lasted 2 years before Garrn broke up with the Hollywood actor. The reason she broke it off? Apparently she’d seen Leo leaving a nightclub… with 20 women!

12. Lorena Rae: 20 Years Old

image source: themirror.com

After his split with Toni Garrn, Leo was spotted out and about with model Lorena Rae, for a short time. They didn’t seem to be ‘official’ enough to hit the red carpet together, but they were spotted out in public a few times after the actor’s relationship with Garrn fell through.

13. Kelly Rohrbach: 25 Years Old

image source: glamourmagazine.co.uk

It’s funny that this is Leo’s shortest relationship to date, and presumably because Kelly had already reached the cut off point of 25 years old! They started dating when she was 25, and it ended before she turned 26. Supermodel Kelly’s split from Leo was reportedly mutual because of ‘busy schedules’!

14. Nina Agdal: 24 Years Old

image source: eonline.com

Leo then dated Danish swimsuit model (he has a type, huh?) after his split from Kelly. They tried to keep their relationship on the down-low, but were spotted enough times taking trips in places like Ibiza and the Bahamas. But things ended between the pair before she turned 25.

15. Camila Morrone: 24 Years Old

image source: thesun.co.uk

Camila Morrone is one of Leo’s most recent relationships, which ended in 2022 – before she turned 25. The (you guessed it) model-turned-actress had been dating Leo for around 5 years before they called it quits. Fun fact: Leo first met Camila when she was 12 years old, too… when he was 34.

16. Kat Torres: 21 Years Old

image source: eonline.com

Brazilian model Kat Torres made some big claims back in 2013 when she said that she and Leonardo DiCaprio were dating but that they had a pact never to talk about their relationship. Well, it turns out the pair were never dating and she’d made it up – no doubt taking advantage of people believing he would date a 21 year old..

17. Rihanna: 27 Years Old

image source: themirror.co.uk

Okay, so this one was only a rumor and Rihanna was 27 at the time and not 25, but we’re not far off! It was believed the singer and the actor dated for a short time after Leo split from model Kelly Rohrbach, as the pair were seen in Paris together, and Leo was said to have gone to her birthday party.

18. Miranda Kerr: 30 Years Old

image source: eonline.com

It was rumored that Miranda Kerr and Leo were dating after the model’s split from her husband Orlando Bloom, but the reason it’s only rumored and not official is probably because she was 30 years old at the time and not 25! Rumors were sparked when they were apparently seen having dinner together – but, of course, friends can have dinner too!

19. Helena Christensen: 29 Years Old

image source: twitter.com

It was rumored that Leo was dating Danish supermodel Helena Christensen around the time of the Titanic premiere back in 1997, when Christensen would have been 29 years old. It was never officially confirmed by either Helena or Leo, but they were apparently seen at plenty of parties together!

20. Demi Moore: 35 Years Old

image source: themirror.co.uk

This one is only a rumor, and most probably because she was way over his cut off age as well as being an actress and not a supermodel! But it’s still alleged that Leo and Demi dated after he split from husband Bruce Willis, as they were spotted together – but they could’ve just been friends!

21. And Now… Other Male Celebs With Much Younger Partners! Michael Douglas And Catherine Zeta-Jones

image source: hellomagazine.co.uk

Michael Douglas and Catherine Zeta Jones have been a famous Hollywood couple for a while – and long since proved they’re in it for the long-term. But that doesn’t change the huge age gap! The acting pair began dating in 1999, when Douglas was 55 years old and Catherine was 30 years old.

22. Zach Braff And Florence Pugh

image source: eonline.com

Although the couple have now reportedly split, they made headlines when they were together for the big gap in age between them! Actor Zach Braff and actress Pugh have a 21 year difference, which received a lot of online hate when they posted openly about their relationship!

23. Dane Cook And Kelsi Taylor

image source: usweekly.com

Comedian Dane Cook has been known to date women much younger than him, as he apparently had a three-year relationship with a Playboy Playmate who was 21 years younger than him. The 50-year-old is now engaged to actress Kelsi Taylor, who is 27 years younger.

24. Eddie Murphy And Paige Butcher

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Not only is actor and comedian Eddie Murphy almost 20 years older than his fiancée Paige Butcher, but he apparently makes a habit of it, too. His dating history includes TV and radio star Rosci Diaz, over 20 years younger than him, and Amber Rose, 23 years younger!

25. Steven Tyler And Aimee Preston

image source: tukonews.com

Rock stars are no strangers to having young girls throw themselves at them, but Aerosmith frontman Steven Tyler is currently in a relationship with his assistant Aimee Preston, who is almost 40 years younger than him! They’ve been happily in a relationship for 7 years, though.

26. Johnny Depp And Amber Heard

image source: cnn.com

We all know how this one turned out, and the 23-year age gap between these two actors was the least of their problems in the end. Johnny was also 10 years older than supermodel Kate Moss when he dated her. Now nearly 60, Depp deserves the single life for a while!

27. Jim Carrey And Ginger Gonzaga

image source: eonline.com

Comedian Jim Carrey, now 61 years old, was previously in a relationship with fellow comedian Ginger Gonzaga – with a 22 year age gap between the pair. Before this, he had a three-year relationship with makeup artist Cathriona White, who was 25 years younger.

28. Hugh Hefner And Crystal Hefner

image source: people.com

We all know Hugh Hefner was surrounded by very young Playboy bunnies during his life, but he was officially in a relationship with women who were 18 years old when he was in his 80s! Crystal Hefner, his wife before he passed away, was 60 years younger than him during their marriage.

29. Kevin Costner And Christine Baumgartner

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Married back in 2004 and still going strong, actor Kevin Costner is actually 20 years older than wife Christine. The pair had been in a relationship for 4 years before officially tying the knot. Kevin was 49 years old when he married the 29 year old model and handbag designer!

30. Bruce Willis And Emma Heming Willis

image source: vanityfair.com

This pair have been married since 2009, and the action movie star is 23 years older than his wife, Emma. The model and actor now have two daughters together, too. The Die Hard actor was 54 when he married 31-year-old Emma, following his previous marriage to Demi Moore.