Photo: Mike Windle / Staff / Getty Images

Money, fame and good looks— Leonardo DiCaprio seems to have it all. So, why in the heck is he still single? He’s certainly dated his fair share of beautiful women, but still no Juliet to his Romeo! Let’s analyze things further and take a look at the list of all of the former Leonardo DiCaprio girlfriends.

He’s definitely a hit with the ladies! The handsome and talented Leonardo DiCaprio is ranked among the best and most influential actors in Hollywood. The 42-year-old star has acted in countless blockbuster movies that have sent the box-office registers ringing such as Titanic, Catch Me If You Can, The Great Gatsby, and Inception. Despite his phenomenal professional success, the Oscar-winning actor has never been married, and continues to flit from one girlfriend to another. Over the years, The Revenant star has become infamous for only dating Victoria’s Secret models and Hollywood actresses. Leonardo DiCaprio’s dating timeline boasts a long and impressive lineup of drop dead gorgeous women who most men could only dream about. Here is a comprehensive list of Leonardo DiCaprio’s girlfriends.

Leonardo DiCaprio Dating Timeline: Who Is Leonardo DiCaprio Dating?

Most men would kill to be in his shoes, but DiCaprio is unfazed by all the female attention he gets on a regular basis. The Wolf of Wall Street superstar has dated beautiful actresses like Blake Lively and Amber Valetta, while his long list of model girlfriends include Gisele Bundchen, Naomi Campbell, Bar Rafaeli, and most recently, Nina Adgal. He has dated a string of Victoria’s Secret and Sports Illustrated models such as Kelly Rohrbach, Toni Garrn, Erin Heatherton, Eva Herzigova and Anne Vyalitsyna. Let’s take a closer look at Leonardo DiCaprio’s numerous girlfriends over the years.

#1. Gisele Bundchen

She is the world’s top supermodel and he is the most famous face in Hollywood. By all accounts, Leonardo DiCaprio and Gisele Bundchen were the epitome of a power couple, and dated from 2000-2004. At the time, the duo topped several lists of most beautiful couples, but the Victoria’s Secret Angel eventually got tired of waiting for the stubbornly single Leo to propose. She is happily married to Tom Brady now, but gave a tell-all interview back then saying, “We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best.”

Gisele Bundchen Dicaprio

Photo: Michael Loccisano / Staff / Getty Images

Also Read: 10 Best Leonardo DiCaprio Movies For Which He Should Have Won an Oscar!

#2. Bijou Phillips

Leonardo DiCaprio and Bijou Phillips were one of Hollywood’s “it” couples in the ’90s, and he even helped her score her first big break in Hollywood. As the daughter of the Mamas and Papas singer, John Phillips, Bijou was no stranger to fame. However, DiCaprio had a big hand in her debut film role in Black and White.

#3. Naomi Campbell

She was the beautiful British supermodel DiCaprio dated way back in 1995, but ended things on amicable terms and remain friends to this day. Campbell and the Django Unchained star have been on several exotic vacations with mutual friends, and are regular fixtures at each others events and fundraisers.

Naomi Campbell Dicaprio

Photo: Frazer Harrison / Staff / Getty Images

#4. Bar Refaeli

While it lasted, DiCaprio and the stunning Israeli model gave fans everywhere relationship envy with their picture-perfect life together. The pair dated for nearly six years and things seemed to be getting pretty serious with engagement rumors floating around. However, the attractive couple headed for splitsville in 2011, and Refaeli is currently expecting her first child with her Israeli businessman/husband, Adi Ezra.

Bar Refaeli leonardo Dicaprio

Photo: Pablo Cuadra / Stringer /Getty Images

#5. Blake Lively

This relationship came as a surprise to many die-hard fans of the beautiful Blake Lively, who is now happily married to Deadpool star, Ryan Reynolds. While she may be the doting mother of two adorable children now, the Gossip Girl actress briefly dated DiCaprio back in 2011. Their five-month long relationship lasted while he was shooting The Great Gatsby and sources gushed, “She spent the whole time baking… Leo’s never dated a girl who can cook. And he’s smitten!”

Blake Lively Leonardo Dicaprio

Photo: Jamie McCarthy / Staff / Getty Images

Also Read: 10 Hottest Blake Lively Pics of All Time

#6. Amber Valetta

According to tabloid fodder back in 1998, DiCaprio happened to glance at a photo of the gorgeous Amber Valetta in a magazine, and hunted her down in person. Apparently, he was so smitten that he had his reps contact her management and set up a date. The twosome allegedly had a brief fling the same year, but it didn’t last long before they headed their separate ways.

#7. Rihanna

If you thought DiCaprio only had a taste for famous models and actresses, think again! Last year, the actor was spotted getting cozy with Rihanna at Coachella, the music festival. The stars have been linked together multiple times over the years, after they were seen dancing flirtatiously at a Paris club, and he allegedly helped plan her birthday party once upon a time!

Rihanna Leonardo DiCaprio

Photo: Frazer Harrison / Staff /Getty Images

#8. Kelly Rohrbach

Probably one of his longest relationships in recent times, DiCaprio dated the Sports Illustrated model for over a year! The blonde beauty is a woman of many talents, being a golfer and a graduate of Georgetown University. DiCaprio and the 27-year-old Rohrbach even sparked rumors of an engagement, but announced their split at the beginning of last year. She will soon be seen in the upcoming highly-anticipated big screen adaptation of the ‘90s TV show, Baywatch.

[etn-inline-post id=”29611″]