Some female celebrities simply choose the wrong men, while others love the honeymoon periods of relationships, so they tend to jump from one to another partner.
Certain names on the list will surprise you, while others are well known for refusing to be single longer than five minutes.
It doesn’t matter whether it was a long-term relationship, a fling, or an entire-blown marriage. This is a rare case where quantity matters more than quality.
We are not judging them but merely stating the facts. So, here are 20 female stars and plenty of their exes.
Ariana Grande: 8
The young singer got engaged on 20th Dec 2020. This time, Dalton Gomez stole her heart. But that’s far from her first engagement.
Ariana dated Graham Phillips for three years, between 2008 and 2011.
Jai Brooks and Grande’s relationship officially lasted for two years, though at the same time, the singer was spotted with Nathan Sykes and Big Sean.
She went on to date Big Sean from 2014 to 2016 and then spent two years with now late Mac Miller. The couple were engaged but decided to split in 2018.
The same year, Grande met Pete Davidson, and the two were also engaged. It was a short romance, but quite intense.
Since the singer is in her mid 20s, we don’t think she will settle down just yet.
Hayden Panettiere: 10
Hayden Panettiere dated Stephen Colletti, her Laguna Beach co-star, from 2006 to 2008. During this relationship, she had a fling with Evan Ross.
She then started dating Milo Ventimiglia for a year. Right before the official ending of this relationship, in 2009, she was spotted with Jesse McCartney.
British TV star Steve Jones and businessman Harry Morton also came into the picture in 2009.
She started seeing athletes, NFL player Scotty McKnight and professional boxer Wladimir Klitschko.
Hayden and Klitschko share a daughter, Kaya Evdokia Klitschko.
Considering she is still young, yet she hasn’t found the one, we are sure Hayden’s list of relationships and flings will continue to grow.
Charlize Theron: 10
It’s not a stretch to say that Charlize doesn’t have a type. Well, she has a soft spot for actors, but that’s about it.
From 1995 to 1997, Charlize Theron dated the American actor and singer Craig Phillip Bierko. From 1998 to 2001, she dated musician/songwriter Stephan Jenkins.
Reportedly, at the time, she had a fling with George Clooney. Right after her break up with Jenkins, she started almost a decade-long partnership with actor Stewart Townsend.
After this long-term relationship ended, Charlize was spotted with Keanu Reeves, then actor Jeremy Renner, Ryan Reynolds, and finally Alexander Skarsgard.
From 2013 to 2015, Theron was dating Sean Penn. Some say they were engaged, but she denied it after the split.
She was then accompanying Eric Stonestreet in 2018, and there were rumors about hooking up with Brad Pitt.
Charlize seems to enjoy being in a relationship, but she clearly chooses the wrong guys. Case in point: Stuart Townsend – Charlize Theron’s ex-partner – has a secret family in Costa Rica. And it started while he was dating the Oscar-winning actress.
Katy Perry: 11
Katy Perry likes her men famous and mostly British.
She was married to Russel Brand and is engaged to Orlando Bloom.
The singer dated Sons of Anarchy actor Johnny Lewis before becoming a global superstar and dedicated him a song, The One That Got Away.
Song Circle the Drain is about her relationship with Travie McCoy.
After her divorce in 2012, Katy dated a French model Baptiste Giabiconi, then guitarist Robert Ackroyd, and during the same year, she started her romance with John Mayer.
Diplo, guitarist Robert Ackroyd, Robert Pattinson, Jared Leto are also on the list of Perry’s flings.
That is not a lot of guys, since the singer is in her mid-30s, but it’s interesting since they are all from show business.
Amber Heard: 10 and counting
Unlike Charlize, who is mainly known for her movie roles, Amber Heard’s private life always overshadows her work.
From 2004 to 2005, she dated the Mexican director, Alejandro Gomez Monteverde. Then she started dating Mexican actor Valentino Lanus, right after the break with the director.
Another singer came to Amber’s life in 2007, Mark Wystrach, followed by actor Crispin Glover.
Then from 2007 to 2008, Sean Faris came into the picture. Again, right after the split, she moved on to Austin Nichols, the fellow actor.
In 2009 Heard was spotted with French producer Arthur Wybrands.
From 2008 to 2012, she was in an on/off relationship with the female photographer, Tasya vee Ree.
And that’s when she met and married Johnny Depp.
During and after the marriage, she was seeing Elon Musk. Then Vito Schnabel and Bianca Butti came into Amber’s life. To be continued…
Jessica Simpson: 11
Though he was not her first boyfriend, Nick Lachey and Jessica Simpson became an iconic couple in the early 2000s. After dating for a year, the two got married, had their TV show, and finally split in 2006.
Apparently, she was seeing Adam Levine in 2004, Fred Durst, and skateboarder Bam Margera, both in 2005. Right after the divorce, she had a brief affair with the comedian Dane Cook. From 2006 to 2007, she dated John Mayer.
In 2007, she was seeing Marcus Schenkenberg until she met NFL star, Tony Romo. The two spent two years together.
Billy Corgan and Simpson were spotted in 2010, though we cannot make sense out of that one.
In 2010 she met Eric Johnson. The couple married in 2014 and now are parents of three.
Clearly, she married Lachey way too early and needed some life and romance experience before finding the one.
Taylor Swift: 12
People like to mock Taylor for her list of exes, but it’s not even that long!
Her whole love life is documented in her songs. In 2008 she dated John Jonas and wrote three songs about the relationship: Last Kiss, Forever and Always, and Holy Ground.
In 2009 she was seeing a model Lucas Till and then moved onto the Twilight star Taylor Lautner. She dedicated him a song Back to December.
Then John Mayer came along. Again. Imagine making the list of all his exes…
After the break-up in 2010, she was seeing actor and musician Cory Monteith and wrote him a song called Mine. At the end of 2010 and in 2011, she dated the actor Jake Gyllenhaal.
Among Taylor’s famous flings are Eddie Redmayne, Harry Styles, Conor Kennedy, and Zac Efron. Styles got two songs: IKnew You Were Trouble and Out of the Woods.
Calvin Harris and Swift dated from 2015 to 2016, and it seemed pretty serious. After the break-up, she had another high-profile relationship with Tom Hiddleston.
Taylor Swift hasn’t spoken much about Joe Alwyn publicly, but they have been dating for at least five years.
Alwyn stated he finds it “flattering” that Swift writes songs about him.
Kate Hudson: 12
Kate Hudson has three kids with three different exes.
In 1998, Kate Hudson started dating Chris Robinson from The Black Crowes. The two got married and had a child in 2000. The divorce came seven years later.
From 2006 to 2009, Kate had an on/off relationship with the actor, Owen Wilson. Then she went on a couple of dates with Dax Shepard and NBA star Baron Davis.
In 2007, Kate had a fling with late Heath Ledger. A year later, she was seeing the professional cyclist Lance Armstrong.
In 2009 she started seeing the professional golfer Adam Scott but soon turned to New York Yankee Alex Rodriguez.
From 2010 to 2014, Kate dated the Muse singer Matthew Bellamy and had another child.
In late 2016 Hudson started seeing a musician/actor Danny Fujikawa. The two had Kate’s third child in 2018.
She was also linked to Diplo, Nick Jonas, and even Matt LeBlanc, back in the late 90s.
Amanda Seyfried: 12
Amanda Seyfried dated the actor Micah Alberti from 2002 to 2006. It was young love, and the two met on the set of All My Children.
While they were on a break, in 2005, she was spotted with Emile Hirsch.
Amanda Seyfried and Dominic Cooper dated for two years, from 2007 to 2010. At the time, she was linked to Alexander Skarsgård as well.
From 2010 to 2011, a blue-eyed actress was seeing Ryan Phillippe. She clearly loved being in year-long relationships since she also dated Desmond Harrington, Josh Hartnett, and Andrew Joblon, all for one year.
She and Justin Long became an IT couple in 2013 and dated until late 2015.
Amanda started going out with Thomas Sadoski in 2016. Amanda and Thomas met on the set of their 2015 off-Broadway play The Way We Get By and did a 2016 film, The Last Word.
Sadoski divorced and married Amanda in 2017.
They have two children.
Natalie Portman: 12
Without the rumors, Natalie Portman’s love life would be pretty dull. That’s why we have to include those who were “maybe” seeing the popular Oscar-winning actress.
It all started in 1998 when young Natalie dated Lukas Haas.
Then Hayden Christensen came into her life, and the two spent a year together.
The story about Portman and Moby is still unclear, but it doesn’t seem that anything happened between the two.
From 2003 to 2006, she dated the actor/director/singer/producer/model Gael García Bernal. After the break-up, she started seeing Andy Samberg and then another actor, Jake Gyllenhaal.
The fling with Jude Law from 2007 remains a mystery, and Natalie went on to date Nathaniel Philip Rothschild and Nathan Bogle.
Singer/songwriter Devendra Banhart stole her heart in 2008, but they called it quits after a year. Natalie met Benjamin Millepied in 2012, on the set of BlackSwan, and they got married soon after.
They share two children.
Kaley Cuoco: 12
Kaley Cuoco and actor-producer Thad Luckinbill started their romance in 2002. Though it’s not clear how long it lasted, her next guy was a model and actor, Kevin Zegers, in 2004.
Two years later, The Big Bang Theory started singer Jared Lowenstein. In 2007 she had two relationships, with actor Josh Henderson and Al Santos.
She spent two years with Johnny Galecki, from 2008 to 2010, her TBBT costar. The following two years, Kaley was with Christopher French, a musician.
In 2012 she got engaged to an addiction specialist named Josh Resnik. Later that year she was back to arms of a musician, this time, Bret Bollinger.
In 2013 Kaley met her future ex-husband, a professional tennis player, Ryan Sweeting. The marriage lasted only a year, from 2015 to 2016.
She went onto date Karl Cook, and they married in 2018.
Scarlett Johansson: 13
Johansson doesn’t truly believe in monogamy, as she stated in a recent interview. But, she seems to love falling in love, and can we blame her?
The actress didn’t confirm all of her affairs, so we have a lot of questions. Like, what was going on between her and Jude Law in 2003?
And what about Benicio Del Toro in 2004? Wasn’t she dating Jared Leto at the time?
We know that from 2005 to 2007, Scarlett and Josh Hartnett were pretty serious. We can’t confirm or deny if anything happened between her and Justin Timberlake. We do know that ScarJo started seeing Ryan Reynolds in 2007, and the two married a year later.
The two divorced in 2011, and it looks like they both cheated. Scarlett was spotted with Sean Penn, and between 2011 and 2012, she dated Nate Naylor, an NYC advertising executive.
Scarlett married French journalist Romain Dauriac in 2014 and divorced him in 2016.
Colin Jost and Scarlett Johansson married last October, and we hope that the third time’s the charm!
Sandra Bullock: 13
Considering that Sandra Bullock is in her mid-50s, it’s safe to say that she didn’t date much.
The actress dated mostly actors, but there were few musicians as well.
Bullock dated an actor Michael Mailer in the late 80s. Between 1992 and 1995 she was spending her days with Tate Donovan, also an actor.
Some still think that during their Speed days, Keanu and Sandra hooked up, but both denied it many years later. I
n 1995, she briefly dated the NFL star, Troy Aikman. From 1996 to 1998, Matthew McConaughey won her heart.
After a fling with Dweezil Zappa, Sandra dated the musician Bob Schneider until 2001. Following the split, she spent less than a year with Hugh Grant and dated Ryan Gosling. Yes, the age gap is freaky, but they were both adults.
The next step was marriage, and she chose West Coast Choppers owner, Jesse James. They were together from 2004 to 2010, when she met Ryan Reynolds, her new leading guy.
Chris Evans and Bullock were briefly together, and in 2015 she started dating photographer Bryan Randall. We cannot say whether they are still going strong, considering there were rumors about the split.
The Queen of everything, Rihanna, is one of those women who excel at everything, but they don’t always choose the best guys.
There were rumors back in 2006 that Riri is with Jay Z. Also, at the same time, she was spotted with Shia LaBeouf. However, her first public relationship came to light in 2007 and it was not pretty.
Rihanna and Chris Brown dated from 2007 to 2009, when he assaulted her. She moved on and had flings with Justin Timberlake and NBA star Rashard Lewis. In 2011, Riri dated Matt Kemp, then a model Dudley O’ Shaughnessy, and finally Ryan Phillippe.
In 2012 Rihanna was spotted with Ashton Kutcher and the following year with NBA player J.R. Smith. In 2015 she reportedly became one of many Leonardo DiCaprio’s girls.
At the same time, Travis Scott came into the picture. As for Drake? Well, he has been on and off since 2009 and went official in 2016.
That didn’t last, and Riri had a new man – the Saudi billionaire, Hassan Jameel. The relationship ended after four years.
Jennifer Lopez: 14 and counting
J.Lo loves to be engaged, married, anything but single. And it would be unfair to say that she was unlucky in love since her exes are always saying the nicest things about her.
That being said, the mom of two recently ended her engagement with Alex Rodriguez. But who were men before an American former professional baseball shortstop?
Back in the early 90s, Lopez dated Chris Paciello, who was in the Mafia. Then in the mid-90s, she went out with Wesley Snipes.
Between 1984 and 1994, she was on/off with the businessman, David Cruz. In 1997 she married a waiter Ojani Noa but divorced in 1998.
Then, in 1999, J.Lo started seeing P. Diddy and this high-profile relationship ended in 2001.
From 2001 to 2003, she was married to her backup dancer, Cris Judd. During that time she met her next big love: Ben Affleck.
In 2003, she was engaged to the actor, but they ended their romance.
Jennifer married once again in 2005. This time, she chose a musician Marc Anthony and the couple had twins. They split in 2011.
After, she dated two actors, Rodrigo Santoro and Bradley Cooper.
Between 2011 and 2014, she dated a young Casper Smart, another backup dancer. At the time, she reportedly had a fling with another dancer, Maksim Chmerkovskiy.
In 2016 she was briefly with Drake, and later that year she met Rodriguez.
Jennifer Aniston: 14
Aniston, apart from few exceptions, dates actors exclusively.
In 1990, she dated Charlie Schlatter. Then she spent four years with Daniel McDonald. She briefly dated Jon Stewart and musician Adam Duritz.
From 1995 to 1998, Jennifer was in a relationship with Tate Donovan. As soon as they broke up, she hooked up with Paul Rudd.
Aniston married Brad Pitt in 2000, but they divorced in 2005 because he felt he was “wasting his life.” The star was caught in a love triangle with Pitt and Angelina Jolie.
She found comfort in Vince Vaughn. Then some say she also hooked up with Matthew Perry.
Like every other Hollywood gal, Jen also fell for John Mayer. They were together for a year, and after that relationship ended in 2009, she had a fling with Gerard Butler.
In 2010, Jennifer was spotted with an NYC businessman Harry Morton. In 2011, she started dating her co-star from Wanderlust, Justin Theroux. They got engaged a year later.
The couple married in 2015 but divorced in 2018.
Sienna Miller: 15
Like Kate Hudson, Miller doesn’t believe in monogamy.
The American-British star first dated Orlando Bloom, back in 2001.
In 2004, she met Jude Law during the filming of Alfie. They were on and off for almost a decade. But, during their time apart, they had other relationships.
In 2005, Sienna was hanging out with Jamie Dornan, as well as with 007 Daniel Craig.
And in 2007, she was hanging out with Josh Harnett, P. Diddy, model Jamie Burke, and even James Franco.
While filming The Edge of Love, Sienna fell for her costar, Matthew Rhys. He was soon replaced by Rhys Ifans, and the two were engaged.
Between 2008 and 2009, she was seeing married Balthazar Getty. Needless to say, people judged her way more than him.
In 2011 she was engaged once again, this time to Tom Sturridge. The couple welcomed a baby girl, and despite the break-up, they are full of support for each other.
In 2016, Sienna was engaged once again. This time it was director Bennett Miller. But, after two years they decided to split, and singe Sienna started seeing Lucas Zwirner. They broke up in 2020.
Sienna is enjoying life, and eventually, she will settle down. If not, she will continue having fun, because that’s also an option!
Halle Berry: 15
Berry’s first big love was Kevin Costner, back in 1989. During the same year she was spotted with singer Danny Wood. In the early 90s, she was with Spike Lee but left him for Wesley Snipes.
At the time she was also seeing Eddie Murphy.
Halle married professional baseball player David Justice in 1992, but they divorced in 1997. Her rebound was Shemar Moore.
From 1999 to 2005, Halle was with Eric Benet, and they even got married in 2001. Due to his infidelities, they ended the marriage. Ultra talented and drop-dead gorgeous actress was single, again.
Post-divorce, she mended her heart with Fred Durst, then Heavy D, and Terrence Howard.
At the same time, she met her future long-term partner, Canadian model Gabriel Aubry. The couple shares a daughter.
In 2013, Halle married the French actor Oliver Martinez, but they divorced in 2016. The following year she was seeing Alexander Grant, AKA Alex da Kid.
Has Halle finally found the one? She is dating Van Hunt, and they recently had a red carpet debut.
Britney Spears: 17
America’s sweetheart started dating golden boy Mario Lopez in 1999. She moved onto the actor Robbie Carrico during the same year and finally met Justin Timberlake.
The two were the hottest pop couple, though their romance ended in 2002, and Britney started dating a choreographer, Wade Robson. She was also spotted with the musician Fred Durst.
Colin Farrell and her backup dancer, Columbus Short occupied Britney’s love life in 2003.
A year later she was married. Young Britney married her childhood friend, Jason Alexander, in Vegas, but there was a quick annulment.
From 2004 to 2007, she was married to her dancer, Kevin Federline, and they share two boys.
After the divorce, Britney had a number of flings: Isaac Cohen, Howie Day, Jonathan Rotem. From 2009 to 2013, she was involved with her agent, Jason Trawick.
A year later, she was seeing a lawyer and bartender named David Lucado.
From late 2014 to 2015, she dated the film producer Charlie Ebersol. Since 2016, Britney has been dating the actor, Sam Asghari, and the two were engaged.
Spears and model Sam Asghar have been dating for a couple of years now. We cannot say whether they are still together.
Drew Barrymore: 30
The former wild child of Hollywood started her career as a toddler. She grew up way too fast, so it’s not surprising that she already had a vast number of relationships.
Drew went out on a date with the actor Christian Bale while she was still a teenager. Then dated poker player Rick Salomon and Corey Feldman, a former child star.
In 1990, she dated Balthazar Getty. From 1990 to 1991, Drew dated another actor, Leland Hayward. Also in 1991, she dated the actor/director David Arquette.
Between 1994 and 1995, she was married to a bar owner. Jeremy Tomas. She then dated Chris O’Donnell and Leo DiCaprio.
From 1995 to 1996, Drew dated the musician Eric Erlandson. Following the split, she hooked up with Edward Norton.
In 1999 she had a short romance with another actor, Henry Thomas. She was in an on/off relationship with The Strokes drummer Fabrizio Moretti for most of the 2000s.
In 2001 she married the comedian Tom Green, but the marriage lasted only until 2002.
She was spotted with Sam Rockwell, Hugh Grant, and other actors and musicians mostly.
Drew married Will Kopelman in 2012, and they had two children together. However, they ended the marriage in 2016.
Since 2017, the actress is in a relationship with David Hutchinson. We are not sure whether they are still together, but we didn’t find reports stating otherwise.
Drew beat addictions, overcome being a child star, and became the story of success. Her love life might be messy, but that’s nothing to lose our heads over.