Kate Moss

Kate Moss might have experienced all the ups and downs of having a relationship. She has been through a broken marriage once. But whenever she just comes from a broken relationship, she always makes sure she looks good and camera-ready as a supermodel.

The businesswoman has been through a lot of flings and short-lived romances, like with Lenny Kravitz, Rhys Ifans, and Russell Brand, among others. In the 1990s, she was described to be a “defined grunge waif chic.” However, some of her famous romances weren’t just for the noise. Some were serious, but sadly, it still didn’t work out to a certain degree. She famously had a relationship with Johnny Depp. Other guys she dated were Antony Langdon, Jefferson Hack, Pete Doherty, and Jamie Hince, to name a few.

Elizabeth Taylor

Elizabeth Taylor had a long list of ex-husbands, lovers, and boyfriends. She was married seven times, but she had been into a relationship more than that. She had dated a lot of men. Taylor married Richard Burton twice, while her last husband was Larry Fortensky. However, the last relationship she had was with Jason Winters that lasted for four years.

In case you didn’t know, and you’ll surely be surprised, Taylor had a romantic relationship with Colin Farrell from 2009 to 2011. However, Farrell revealed they never officially ended their romance. In the late 1990s, she also dated Rod Steiger. She also had a thing with George Hamilton in 1987, with Victor Luna from 1983 to 1985, and Anthony Geary from 1982 to 1984. To some degree, she was never out of a man in her life.

Zsa Zsa Gabor

Aside from leaving a legacy in Hollywood, Zsa Zsa Gabor also got the credit for being one of Tinseltown’s most eligible ladies. She had nine marriages and numerous relationships, giving her prolific love life. Her name was liked to dozens of A-list stars and even a prince.

Gabor was married to Frédéric von Anhalt for 30 years, Felipe Alba for just a year, Michael O’Hara for six years, Joshua S. Cosden, Jr. for one year, Herbert Hunter for four years, George Sanders for five years, Conrad Hilton for five years, and Burhan Belge for four years. Relationship-wise, she had romances with Prince Aly Khan, Baby Pignatari, Harry Karl, John F. Kennedy, Frank Sinatra, Richard Nixon, Sean Connery, and the list goes on!

Joan Collins

Joan Collins has one of the most beautiful faces in Hollywood during her time. No wonder she has been through numerous relationships over the years. She has tied the knot five times throughout her lifetime, and she is currently married to Percy Gibson, who is 18 years her junior, for 18 years.

Her former husbands were Peter Holm for two years, Ronald S. Kass for 11 years, Anthony Newley for eight years, and Maxwell Reed for four years. When it comes to boyfriends, Collins can have the credits for having a long list of that. She had romances with Tim, Bill Wiggins, Ryan O’Neal, Warren Beatty for four years, Paul Newman, Ramfis Trujillo, George Englund for one year, Conrad Hilton, and even his son, Conrad Hilton Jr..

Sharon Stone

As one of the most famous actresses and models, Sharon Stone has also dated equally popular men back then. Some of the most notable personalities Stone had a relationship with were Craig Ferguson and Rick Fox. But aside from these two, there is a long list of men that the Basic Instinct star had a romance with.

Stone dated David DeLuise in 2014, while she also went out with Chase Dreyfous in 2008. In 2006, she went on to date Christian Slater. For a year, she had a thing with Craig Ferguson. But in 1998, she tied the knot with Phil Bronstein, although they parted ways in 2004. There are a lot of other guys that Stone dated in the past, with the degree of her beauty, this news is not surprising at all.

George Clooney

Another A-list actor on the list who has dated the best and brightest is George Clooney. He used to be known as a notorious playboy before she settled down with the human rights attorney Amal Almuddin in 2014. Although he also used to be married to Talia Balsam, things between them also ended, and he went on to date several women.

Clooney and Kelly Preston used to live together before they became famous. He then dated Balsam and tied the knot in 1989 and parted ways in 1993. After that, he had a thing with Kimberly Russell after a few years, but they broke up too. He then met Celine Balitran in Paris and dated for three years. He also had romances with Krista Allen, Lisa Snowdown, Carole Radziwill, and Renee Zellweger.

Britney Spears

Britney Spears now looks better after all the issues she has been through. She is now happily in love with her personal trainer boyfriend, Sam Asghari. But before she finds this happiness, she has dated a lot of guys, like Reg Jones, with whom she had a relationship when she’s still in high school.

One of her most famous relationships in the business is with Justin Timberlake. They used to receive credits for being an iconic celebrity from 1998 to 2002. She then went to have romances with Wade Robson, Fred Durst, Colin Farrell, Columbus Short, Jared Leto, Jason Alexander, her ex-husband Kevin Federline, J.R. Rotem, Howie Day, Criss Angel, Adnan Ghalib, Jason Trawick, David Lucado, and Charlie Ebersol.

Cameron Diaz

Cameron Diaz had been in several relationships with actors, singers, athletes, and even businessmen before she finally settled with her current husband, Benji Madden, in 2015. After being engaged for just 17 days, the two decided to tie the knot. Now, they seem to have insurance to a happy family with the arrival of their first kid.

But before they met, Diaz briefly dated Elon Musk in 2013. She also had a thing with the baseball superstar Alex Rodriguez for a year. She was also linked to Adam Levine in 2010 and rumored to have dated Keanu Reeves. Diaz and Paul Sculfor, too, had a brief romance after she went out with Gerard Butler, Sean Combs, and Bradley Cooper. Other guys she had affairs with were Kelly Slater, Tyrese Gibson, Jude Law, Justin Timberlake, and Robbie Williams, among others.

Jennifer Love Hewitt

Jennifer Love Hewitt may have dated a lot of popular men in the industry. Before she officially tied the knot with her current husband, Brian Hallisay in 2013, she had been with several guys before. She had different degrees of relationships, from flings to serious.

Some of the well-known men she dated were John Cusack, John Mayer, Enrique Iglesias, Alex Beh, Jamie Kennedy, Ross McCall, Wilmer Valderrama, Scott Austin, Will Estes, Kip Pardue, Patrick Wilson, Rich Cronin, Carson Daly, Andrew Keegan, Will Friedle, Joey Lawrence, and Fred Savage. However, when she met Hallisay in 2012, her point of view of dating changed. The two worked together for the movie The Client List. From here, the rest is history, taking them to where they are now.

Grace Kelly

She was one of the most beautiful women in the world, so it’s no surprise that Grace Kelly had made a lot of men fell for her. Her dating history was quite controversial because she was linked to her already married co-stars. However, all the controversies died down when she finally settled down and tied the knot with the Prince of Monaco, Rainier III, earning her the credits of being the Princess of Monaco, in 1956.

But before she became the Grace of Monaco, Kelly used to have a relationship with Bing Crosby after they met on the set of their movie together, The Country Girl. Some of his famous exes were William Holden, Australian director Robert Dornhelm, David Niven, Jean-Pierre Aumont, Marlon Brando, John F. Kennedy, Spencer Tracy, and Frank Sinatra, to name a few.