Relationships are hard.
We think that the stars have it easier when it comes to hooking up and dating around. After all, they’re gorgeous, famous, rich, talented – who wouldn’t want to date them? Alas, like a buffet with too many options, celebrity culture can make it impossible for stars to find someone who’s in it for the long haul. Take Taylor Swift, for example, who charts her own relationships and their trouble through her song lyrics and candid interviews. Unlike her male counterparts, who also sing about their own long lists of ex-lovers, Swift named hers – or at least provided enough clues for savvy fans to guess as to their identities. As a result, her romantic history has been picked apart and made the subject of jokes and jabs, but is she really alone in having relationship troubles, or does she just get the most press for it?
These 15 female celebrities all have their own rocky history when it comes to romance. From ex-husbands to canceled engagements to public arrests to public disses, no stone has gone unturned when it comes to love that’s been lost. Don’t worry, Taylor, these 15 ladies prove that you’re in good company!
15 Katy Perry: On-Off Wonder
Katy Perry has recently been spotted again with on-off boyfriend Orlando Bloom, but she’s had numerous messy relationships in the past that rival her enemy Taylor Swift! Let’s take a look back, shall we?
When the singer first burst onto the scene in 2006, she was dating Gym Class Heroes singer Travie McCoy, even starring in his music video for “Cupid’s Chokehold”. According to POPSUGAR, they split over McCoy’s substance issues and Perry later got involved with comedian Russell Brand, marrying him in 2010. Things turned sour between the pair after just 14 months together and Brand ended things via text message – the last time they ever spoke. Then came an on-off relationship with womanizer John Mayer (another point in the T-Swift column, who also calls the musician an ex) before she moved on to Diplo and, most recently, Orlando Bloom, where she’s been running things hot and cold again!
14 Drew Barrymore: 3 Divorces By 40
As a former wild child who struggled with substances by the age of 13, Drew Barrymore didn’t exactly have healthy relationships to base her own experiences on, which might explain why she’s been divorced three times! According to POPSUGAR, Barrymore has been with an impressive 17 men during her tenure in the spotlight, including big names like Edward Norton, Luke Wilson, and Hugh Grant!
When it comes to marriage, though, the actress has been pretty unlucky. After her first time walking down the aisle to bar owner Jeremy Thomas, the couple split less than a year later. Then, she tied the knot with comedian Tom Green – which again lasted less than a year. Finally, most recently, she wed art consultant Will Kopelman, with whom she shares two daughters. Perhaps unsurprisingly, that marriage ended in divorce too, this time less than four years later.
13 Jennifer Lopez: Likes Her Flings
Jennifer Lopez is a woman who loves love, but she certainly doesn’t seem to be very lucky in it! Drama has plagued most of her highly-publicized relationships, but her reputation as a man-eater hasn’t dampened her appeal.
Like Drew Barrymore, Lopez has also been married (and divorced) three times, with her first husband Ojani Noa threatening to release intimate material starring a young J.Lo! Then, there was the infamous relationship with Diddy, which, according to NYMag, culminated in a shootout at a nightclub, a trip down the aisle again with backup dancer Cris Judd, and, of course, the notorious engagement to actor Ben Affleck, which gave us the flop Gigli and the practice of celebrity portmanteaus. Bennifer, anyone? Following Affleck, there was marriage and children with singer Marc Anthony, a lengthy on-off relationship with boy toy Casper Smart, a fling with Drake, and, most recently, a relationship with baseball player Alex Rodriguez!
12 Amber Rose: Dissing & Dishing
While Amber Rose hasn’t yet racked up a list of famous men she’s been involved with, two she’s had on her arm have had their fair share of drama where the former dancer and model is concerned.
With rappers Kanye West and Wiz Khalifa as her two famous exes, Rose has seen her relationship history laid bare for everyone to see, thanks to the former’s volatility on Twitter! From 2008 to 2010, West and Rose dated, and things did not end well. West moved on to Kim Kardashian while Rose took up with Khalifa, who she married and had a child with. After 14 months of marriage, they split, but it was really the Kardashian drama involving Kylie Jenner, Tyga, and Rose’s BFF Black Chyna that got West on Twitter, where he made inappropriate comments to Khalifa about Rose and their history in an expletive-laden rant.
11 Scarlett Johansson: Loved & Lost
As one of the most beautiful actresses in the business, Scarlett Johansson is no stranger to breaking hearts. While she might be the Black Widow in the Avengers franchise, the Oscar nominee hasn’t always had the upper hand when it comes to her troubled relationship history.
Boasting big-name exes like Justin Timberlake and Jude Law, Johansson was first married to Ryan Reynolds from September 2008 to December 2010, and Johansson called the subsequent divorce “horrible” and “devastating” in an interview with Vogue. Then, in 2014, the actress got back up on the nuptial horse, this time with journalist Romain Dauriac, with whom she shares a daughter. The marriage fizzled out after just two years, but we think that, if history repeats itself, it won’t be the last trip down the aisle for Johansson.
10 Britney Spears: Bad Influences
Having her relationships dissected by tabloids for years following her major split from Justin Timberlake as the ideal couple of the early ‘00s, Britney Spears has had bad influence after bad influence in all subsequent relationships. First there was backup dancer Kevin Federline, who was lauded by the media as the stereotypical deadbeat. The singer loved him, though, and their divorce was the straw that broke the camel’s back that led to her notorious 2007 breakdown. Following K-Fed, there was an engagement to agent Jason Trawick – who was named as a co-conservator over the troubled star – and a cheating scandal with lawyer David Lucado.
Now, the singer is seeing aspiring actor Sam Asghari, and while things seem to have settled down for Spears, anyone with a 55-hour marriage on their resumé definitely has a troubled romantic past!
9 Kim Kardashian: Ran Around Before Settling Down
We’ve already discussed Kim Kardashian’s relationship with Kanye West, who is the father of her three children, but before the rapper, Kardashian wasn’t exactly a role model for healthy relationships.
After tying the knot for the first time at the age of 19, Kardashian’s romantic history was a tangled web. From an intimate personal tape with Ray J that catapulted her to fame to the 72-day marriage to NBA player Kris Humphries, Kardashian was showing us all the things NOT to do when you’re trying to navigate the waters of love. Kardashian’s marriage to Humphries was largely seen as a cash-grab – even by the groom himself, who wanted to have it annulled on the basis of fraud! What followed was a lengthy series of proceedings that didn’t end until Kardashian was seven months pregnant with her first child by West!
8 Mariah Carey: Princess Problems
Mariah Carey is known for her diva-like behavior, so it shouldn’t be a surprise to anyone – her husbands included – that she’s jumped from relationship to relationship, each one troubled.
First, the chanteuse wed music exec Tommy Mottola, who was 19 years her senior. In the fallout after their four-year marriage fell apart, Carey described Mottola as “overpowering” and “controlling” on her E! show Mariah’s World. Mottola corroborated some of this in his memoir, according to Billboard, saying that their union was “absolutely wrong and inappropriate”. Later, Carey married Nick Cannon, but, before the ink was dry on those divorce papers, Cannon was airing their dirty laundry, saying that they were living in separate homes. The drama surrounding the divorce saw Carey breaking down several times in concert, and, even though she’s moved on, it doesn’t always seem rosy for the singer.
7 Khloe Kardashian: Heartbreak & Hoop Stars
While Khloe Kardashian has stepped into motherhood and is blissful in this new chapter of her life, things weren’t always so joyful for the youngest Kardashian sister.
In pursuit of the fairytale ending, Kardashian wed NBA star, Lamar Odom, after only a month of knowing him! Stability was clearly not a factor for the couple, who endured many ups and downs before finally calling it quits in December of 2016. Of course, that wasn’t before a reality show charted the progression of their union and saw Kardashian try to get pregnant to no avail, but it was really Odom’s issues with substances and infidelity that saw everything collapse. Considering how much darkness she’s gone through, it’s tough to see what the outcome will be for Tristen and herself.
6 Kris Jenner: Change Is A Hard Thing
The Kardashian-Jenner family simply isn’t lucky in love! While on the outside it seemed that Kris Jenner was enjoying a stable and loving relationship with Caitlyn Jenner prior to her transition, rumors began seeping out that the marriage was not nearly as cheery as it seemed, despite the multitude of coordinated family photos.
Conflicting reports by all Kardashian-Jenners have abounded, with Caitlyn claiming that Kris knew about her inner turmoil and desire to transition and Kris saying that she was blindsided by the news. In the fallout of Caitlyn’s reveal as being transgender, the couple divorced and things have been strained between Caitlyn and the rest of the family. When relationship troubles extend to the remainder of the clan, there’s definitely more struggle than your standard T-Swift song that’s for sure!
5 Naya Rivera: Serious Allegations
When a relationship involves allegations from one partner against the other, it’s clearly not a healthy situation, but actress Naya Rivera is no stranger to unhealthy relationships.
To start, there was her on-screen and off-screen love affair with Glee costar Mark Salling, which later ended less than amicably (Rivera keyed his car). Following the release of charges against Salling, Rivera said she wasn’t that surprised! What followed was an engagement to Big Sean, which ended amid rumors of his infidelity and her jealousy, and a wedding to Ryan Dorsey, which is where these images come into play! In November 2017, Rivera and Dorsey had a disagreement which ended with Rivera in handcuffs. We’re all for a little fire in a relationship, but when it turns to violence, that’s where we draw the line.
4 Halle Berry: All’s Fair In Love And War?
She’s flown under the radar for a woman with relationship troubles, but make no mistake: even the gorgeous Halle Berry isn’t immune to a little heartache. Married three times – first to baseball player David Justice, which ended in a restraining order; second to singer-songwriter Eric Benét, who claimed abnormal circumstances as the reason for the split; and thirdly to actor Olivier Martinez, which is where our story gets juicy.
Prior to Martinez, Berry was in a long-term relationship with model Gabriel Aubry, with whom she shares a daughter, Nahla. When Martinez and Berry wanted to bring Nahla to live in France with them, Aubry made it clear that he was not onboard with the sudden change. For her part, Berry has said that she feels “guilty and responsible” for her failed relationships in an interview with Us Weekly.
3 Rihanna: Bad Gal RiRi Vs. Bad Guy Chris Brown
Bad Girl RiRi has had a thing for bad boys, but it was one bad boy in particular that catapulted her so near the top of our list.
Chris Brown has earned himself a permanent black mark on his record, even as he’s continued to release music. As the infamous story goes, back in 2009 following a night at the Grammy Awards, Brown and Rihanna had an altercation. Suffice to say, it certainly qualifies as relationship troubles that far outweighs Taylor Swift’s latest complaints about a neglectful boyfriend or cheating ex.
While the pair reunited briefly afterward – and Brown still tries to get his ex’s attention via Twitter and Instagram – this messy situation seems merciful over and done with.
2 Angelina Jolie: Love ‘Em & Leave ‘Em
The most famous ex of Angelina Jolie is, of course, Brad Pitt, but he wasn’t the first co-star she set her sights on. Jolie’s string of exes she’s shared the screen with include ex-husbands Johnny Lee Miller (Hackers) and Billy Bob Thornton (Pushing Tin) as well as lovers Jenny Shimizu and Colin Farrell. However, it was really Brad Pitt who made the greatest impact.
The couple got together while Pitt was still married to Jennifer Aniston, and only wed after spending ten years together. Despite sharing six children and reinventing herself as an earth mother type and humanitarian, Jolie showed that she was still a bad girl at heart when she accused Pitt of various misconducts in an attempt to gain full custody. Playing dirty, indeed!
1 Jennifer Aniston: Relationship Tabloid Fixture
Not to be outdone by the woman who stole her man, Jennifer Aniston has spent much of her career painted as the perpetual spinster – a woman who desperately wants children but is never pregnant, a woman who is constantly losing her lovers, a woman who is always without a man.
After Brad Pitt cheated on – and subsequently split from – Aniston, the actress embarked on a series of relationships that included the likes of John Mayer, Vince Vaughan, and Gerard Butler before meeting Justin Theroux. Unfortunately, even from the outset, rumors plagued the couple that they weren’t happy. Theroux spent much of their marriage in Australia filming or in New York while Aniston stayed in California, and the distance between the pair grew even wider when they announced their separation. While Aniston doesn’t have the “maneater” reputation of Taylor Swift, she certainly understands the feeling of having your relationship woes dissected by the media!
References: popsugar.com, popsugar.com, popsugar.com, complex.com, popsugar.com, popsugar.com, people.com, stylist.co.uk, billboard.com, eonline.com, hollywoodlife.com, dailymail.co.uk, usmagazine.com, etonline.com, dailymail.co.uk, nydailynews.com, usmagazine.com, billboard.com, popsugar.com, thestir.cafemom.com, elle.com