20 Celebs Who Had So Many Failed Relationships (They'll Probably Be Alone Forever)

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.

20 Taylor Swift

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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.

19 Lindsay Lohan

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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.”

18 Jennifer Aniston

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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.

17 Drew Barrymore

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The actress Drew Barrymore is a stunning woman so we’re not surprised that she too has dated many men. Her ex-boyfriends include The Strokes drummer Fabrizio Moretti, Corin Nemec, Jamie Walters, and David Arquette among many others.

It is also rumoured that at some point in her life Barrymore hooked up with Edward Norton, Leonardo DiCaprio, and Heather Graham. Interestingly, Christian Bale has recently revealed that he went on a date with Barrymore when they were both teenagers but that he never heard from her again after the date.

The actress has also been married three times – she married Jeremy Thomas in 1994 and divorced him in 1995, married Tom Green in 2001 and divorced in 2002 and married Will Kopelman (pictured above) in 2012 and divorced him in 2016. Currently the actress is said to be dating the businessman David Hutchinson. How long will this relationship last? Probably not very long.

16 Johnny Depp

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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.

15 Cameron Diaz

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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.

14 Kate Moss

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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.

13 Kate Hudson

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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.

12 Rihanna

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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.

11 Madonna

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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.

10 Miley Cyrus

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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.

9 John Mayer

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The singer and song-writer John Mayer is a good-looking man so it comes as no surprise that he has had many relationships. Indeed, Mayer has dated many A-listers – his ex-girlfriends include Vanessa Carlton, Jennifer Love Hewitt, Jessica Simpson, Minka Kelly, Jennifer Aniston, Reena Hammer, Taylor Swift and Katy Perry (pictured above).

Mayer is also rumored to have dated Renee Zellweger, Kim Kardashian and Scheana Marie. Currently, it is rumored that Mayer is dating the star of Rich Kids of Beverly Hills, Dorothy Wang. They were spotted together last month celebrating Wang’s birthday. In fact, both of them arrived in the same party bus! Could that mean that they are hooking up or even dating? Who knows!

8 Kirsten Dunst

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The actress Kirsten Dunst is another Hollywood celebrity that has had quite a few failed relationships. Over the years Dunst has dated numerous men, including Jake Hoffman, Ben Foster, Jake Gyllenhaal (pictured above), Johnny Borrell, Jacob Soboroff, Jason Boesel, and Garrett Hedlund.

Dunst is also said to have dated Justin Long, The Strokes drummer Fabrizio Moretti, Adam Brody and Tobey Maguire. In the case of the latter rumor, while neither Dunst nor Maguire confirmed that they briefly dated, Spiderman director Sam Raimi did, albeit in a very roundabout way.

While Dunst has had quite a few failed relationships, she is not currently single. In fact, she is dating the actor Jesse Plemons whom she met in 2016 while filming Fargo. Last year the couple got engaged. But will they actually get married? Only time will tell.

7 Jennifer Love Hewitt

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The actress Jennifer Love Hewitt has had a tumultuous love life. Indeed, the actress has dated quite a lot of men. Her past boyfriends include Fred Savage, Joey Lawrence, Carson Daly, Diego Serrano, Wilder Valderrama, Rich Cronin, Patrick Wilson, John Mayer, Kip Pardue, and Scott Austin and Ross McCall (pictured above - the pair was even engaged at one point during their relationship) among many others.

It is also said that Hewitt has hooked up with a number of famous men such as Enrique Iglesias. Currently Hewitt is married to the actor Brian Hallisay and the pair has two children together. However, if we have learned anything from this post it is that marriage in Hollywood rarely lasts!

6 Justin Timberlake

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Justin Timberlake is a famous man and he is not bad looking either. So it only makes sense that he has had quite a few relationships. Timberlake’s ex-girlfriends include Danielle Ditto, Fergie (pictured above), Veronica Finn, Britney Spears, Nicole Appleton, Alyssa Milano, Staci Flood, Tatyana Ali, and Cameron Diaz.

As most celebrities, Timberlake also hasn’t escaped romantic linking. Over the years he has been linked to Olivia Munn, Rihanna, and Scarlett Johansson, among many other women. In 2007 Timberlake started dating the actress Jessica Biel and the pair got married in 2012. Their marriage is still going strong but nothing is permanent in Hollywood.

5 Paris Hilton

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Paris Hilton has had so many failed relationships that we have no doubt she’s going to end up alone! Hilton’s ex-boyfriends include Randy Spelling, Edward Furlong (pictured above), Nick Carter, Fred Durst, Kid Rock, Tyler Atkins, and businessman Thomas Gross among many others.

Of course, rumour has it that Hilton has also dated such A-listers like Leonardo DiCaprio and has been photographed in close quarters with the likes of 50 Cent and Jared Leto, frontman of Thirty Seconds To Mars.

She has also been engaged to Jason Shaw. Currently however Hilton is engaged to the actor Chris Zylka. She has said – “I am so excited to be engaged to the love of my life and my best friend. I have never felt so happy, safe and loved. He is perfect for me in every way and showed me that fairytales really do exist!” We’ll see how long that will last!

4 Courtney Love

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Despite her name, Courtney Love doesn’t seem to be very lucky in love at least not based on her past relationships. Love has dated countless of men and her ex-boyfriends include Roddy Bottum, Dave Navarro, Billy Gould, Edward Norton, Jesse Camp, Scott Weiland, Jim Barber, Billy Corgan, and Noel Fielding.

Love has also possibly dated Mickey Rourke, Jamie Burke and Russell Brand. She has also been married twice. In 1989 she married the vocalist James Moreland but their marriage was annulled later that same year. In 1992 Love married Kurt Cobain (pictured above) and the pair remained married until his death in 1994. Considering all her relationships, the one that really goes down in history is her relationship with Kurt Cobain, but mostly because he is a legend.

3 Kelly Osbourne

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Kelly Osbourne has also not been particularly lucky in love and has had quite a few failed relationships. Over the years she has dated men such as Bert McCracken, Danny Jones, Luke Worrall, Rob Damiani, Anton Lombardi, Matthew Mosshart, and Ricki Hall (pictured above).

It is also said that Osbourne dated Quincy Brown, Nick Grimshaw, Josh Hansen, Matty Derham and Kevin Zegers.

Last we heard Osbourne was dating a man named Mario Cuomo who is the lead singer of The Orwells. We’re sure that he’s not Osbourne’s last boyfriend though! Not to mention the fact that she comes from a very strange family, so maybe it's not entirely her fault that she cannot keep a stable relationship.

2 Lil Wayne

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The rapper Lil Wayne has had relationships with quite a few women, including Toya Carter (whom he married in 2004 and divorced in 2006), Lauren London, Nivea, Adrienne Williams-Bosh, Trina, Sarah Bellew, Shenelle, Zena Foster, Candace Cabrera, Dhea, and Christina Millian (pictured above).

Lil Wayne has also been romantically linked to women such as Skylar Diggins, Nicki Minaj, Dana Lee, and Tammy Torres.

All of these failed relationships make us think that Lil Wayne will end up alone. After all, it is said that famous people find it harder to commit – no wonder most of them date more than any normal person. Plus, let's be really honest, we're pretty sure Wayne has a ton of problems, which is probably why he can't keep a girlfriend in the first place.

1 Drake

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The Canadian rapper Drake has also dated countless of women. Unfortunately, all of his relationships have failed which makes us believe that he will end up alone. Which is super unfortunate considering he is known to be a very nice man.

Drake’s ex-girlfriends include Catya Washington, Maliah Michel, Rihanna, Serena Williams, Dollicia Bryan, Sophia Marie, Jhonni Blaze, Shaye G, and India Love.

Drake has also been rumoured to have dated Nicki Minaj (although both of them deny these rumours) Rita Ora (both claim they’re friends) Amber Rose, Jennifer Lopez and Hailey Baldwin. Drake has also confessed that at one point he went on one date with Tyra Banks. It really is a shame that what they say is true: nice guys finish last.

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