Celebrities have a tough life – they are constantly in the news and their actions and life choices are forever being dissected and discussed by the media, their fans and their haters.
If you are a celebrity, it is incredibly hard to maintain your private life, especially your romantic life. After all, fans love hearing anything and everything about their favorite celebrity’s romantic relationships.
Still, celebrities try to maintain their private life as private as possible, often keeping their affairs and their relationships secret until it is no longer possible to do so. However, even though celebrities must maintain half of their affairs a secret we are still astounded by the number of relationships that most celebrities have had.
However, we do understand them – most celebrities are rather good-looking and it is so hard to just stick to one person when you believe that there might be someone else - possibly someone better - out there. The only problem is, by searching for that perfect person celebrities may end up utterly and totally alone.
10. TAYLOR SWIFT
The singer Taylor Swift is well known for her numerous failed relationships probably because she almost always ends up writing songs about her ex-boyfriends.
Over the years, Swift has dated Joe Jonas (he broke up with her over the phone and inspired her to write Forever & Always), Taylor Lautner (inspired Back To December), John Mayer (was the inspiration behind Dear John), Jake Gyllenhaal (inspired We Are Never Ever Getting Back Together), Conor Kennedy (rumoured to have inspired Begin Again), Harry Styles (inspired I Knew You Were Trouble), Calvin Harris (inspired Look What You Made Me Do) and Tom Hiddleston, which for the moment, has avoided having a song written about him.
Of course, the above relationships are just the ones we know of – there could have been more! Currently Swift is dating the actor and model Joe Alwyn, pictured above.
9. LINDSAY LOHAN
The actress Lindsay Lohan has had countless of partners and failed relationships. Her ex-boyfriends include Aaron Carter, Harry Morton, Calum Best, Egor Tarabasov (pictured above) and Ozzy Lusth among many others. She has also dated women, including Samantha Ronson but has since said that that was the result of her L.A lifestyle – “Yeah. I was living in L.A. I’m not saying it’s a bad thing.”
Of course, Lohan has also been rumoured to have dated or at least been with countless of A-listers. In 2014 Lohan apparently hand-wrote a list of the famous men she has had relations with, including Justin Timberlake, Zac Efron, Adam Levine, and Joaquin Phoenix.
Currently it seems like the actress is not dating anyone. In a recent interview she said – “I don’t think anyone could be in a relationship with me because I’m never there all the time.”
8. JENNIFER ANISTON
Jennifer Aniston, still best known as Rachel from the TV show Friends, has also dated a lot of men. Her ex-boyfriends include Charlie Schlatter, Daniel McDonald, Adam Duritz, Tate Donovan, Paul Rudd, Vince Vaughn, and John Mayer.
Aniston is also rumoured to have dated Jon Stewart (we do know that they had dinner together), Paul Sculfor, Gerard Butler, Harry Morton and even her Friends co-star, Matthew Perry!
In 2000 Aniston married Brad Pitt (pictured above) but the couple divorced in 2005. In 2011 the actress started dating Justin Theroux and in 2015 the pair got married. But as recent news have shown, that relationship also didn't last.
7. JOHNNY DEPP
Johnny Depp is not only a talented actor but also a beautiful man. Thus, it comes as no surprise that he has dated countless of women, including the Twin Peaks actress Sherilyn Fenn (they were reportedly engaged but parted ways due to careers), Winona Ryder, Tatjana Patitz, Kate Moss and of course Vanessa Paradis (they dated from 1998 to 2012).
He is also rumoured to have been with A-listers such as Ashley Olsen, Eva Green, Angelina Jolie, Penelope Cruz and Naomi Campbell.
Depp has also been married two times. In 1983 he married the makeup artist Lori Allison but they got divorced in 1985 and in 2015 he married Amber Heard (pictured above) but they got divorced in 2017.
6. CAMERON DIAZ
Cameron Diaz is another celebrity who has a great number of failed relationships. Over the years the actress has dated countless of men, including Carlos de la Torre, Matt Dillon, Jared Leto, Justin Timberlake (pictured above), Kelly Slater, Sean Combs, Paul Sculfor, and Alex Rodriguez.
Of course, Diaz has also not escaped rumours – it is said that she has dated the business magnate Elon Musk, Bradley Cooper and Keanu Reeves as well as with Adam Levine, Gerard Butler, and Tyrese Gibson. In 2014, the actress started dating the guitarist Benji Madden and the couple married in 2015. How long will their marriage last? Probably not very long.
5. KATE MOSS
The stunning model Kate Moss has also dated many men and as is so often the case with celebrities, she has countless of failed relationships. Moss has dated men such as the guitarist Jeordie White, Aviv Nevo, Antony Langdon, Johnny Depp (pictured above), the Prince of Venice and Piedmont Emanuele Filiberto, Pete Doherty and Jefferson Hack among many others.
Rumour has it that she has also been romantically involved with Russell Brand, Jamie Dornan, Daniel Craig, Billy Zane and John F. Kennedy Jr. In addition, Moss said that she kissed Sinatra in 1995.
In 2011 Moss married The Kills musician Jamie Hince but their marriage did not last long – they got divorced in 2016. Unfortunately, that is really no big surprise.
4. KATE HUDSON
Ever wondered how many men the actress Kate Hudson has dated? Quite a lot, it turns out! And unfortunately, none of her relationships ended well – indeed, all of them have failed.
Hudson’s ex-boyfriends include the actor Owen Wilson (they met on the set of You, Me and Dupree and had an on-again and off-again relationship), actor Dax Shepard, Lance Armstrong, Alex Rodriguez, and the musician Matthew Bellamy (pictured above), who was her long-term partner and whom she dated from 2010 to 2014.
It is also rumored that Hudson has dated DJ Diplo, Nick Jonas, Adam Scott and Heath Ledger. Hudson has also been married to the musician Chris Robinson – the couple married in 2000 and divorced in 2007. Currently Hudson is dating the music executive Danny Fujikawa.
3. RIHANNA
The singer Rihanna has also dated countless of men but unfortunately none of her relationships turned into anything serious. Over the years Rihanna has dated the singer Chris Brown (pictured above - they started dating in 2007 and separated after Brown hurt Rihanna in 2009. Nevertheless they got back together in 2012 for a while), Matt Kemp, Travis Scott, and the Saudi billionaire Hassan Jameel.
It is also rumored that Rihanna has been on an on-again and off-again relationship with Drake and that she has also dated Leonardo DiCaprio, Ashton Kutcher, Ryan Philippe, Rashard Lewis, and Justin Timberlake. The actor Shia LaBeouf has also confessed that he went on one date with the singer but their one date did not lead to anything more serious.
2. MADONNA
Madonna and her lovers are always in the news and that’s not surprising seeing as the Queen of Pop can’t seem to maintain her relationships. Over the years, Madonna has dated the American screenwriter Dan Gilroy, the artist Jean-Michel Basquiat, Mark Kamins, John Benitez, John F. Kennedy Jr., Warren Beatty, Vanilla Ice (pictured above) and Tupac Shakur among many others.
Madonna is also rumored to have dated Michael Jackson! The singer has also been married twice. Her first marriage was to Sean Penn – the pair married in 1985 and divorced in 1989. Her second marriage was to Guy Ritchie whom she married in 2000. Their marriage lasted eight years.
1. MILEY CYRUS
Ever wondered who the singer Miley Cyrus has dated? Wonder no more! Over the years Cyrus has dated quite a few men including Nick Jonas, Justin Gaston, Liam Hemsworth, and Patrick Schwarzenegger (pictured above).
She has also been rumored to have dated Jared Leto, Kellan Lutz, Mike Will Made It, and Josh Bowman among many others. Interestingly, Dylan Sprouse confessed that he went on a date with Cyrus in 2006. It is also said that Cyrus and Justin Bieber also went on a date.
Nowadays Cyrus is dating Liam Hemsworth once again and things are looking serious. However, judging by the length of Cyrus' previous relationships, this one is not going to last either.