Ah, celebrity love. Some celebrity relationships seem like real-life fairy tales. Others inspire internet ships that live on long after the relationship is over. And, yes, there are also star unions that aren’t so perfect, including some that seem doomed from the start. It’s one thing when that skepticism comes from the masses on social media, who weigh in on the lives of people they’ve never actually met (no matter how much their in-depth Insta feeds might make us feel like we know them). It’s a lot more concerning (and, let’s be honest, a lot more telling) when those red flags are raised by people who actually know something about the situation.
Whether the warnings have come from friends within their own inner circles or from a tell-it-like-it-is ex on either side of the relationship, these famous folk were all warned about a relationship. Oh, and another (truly unfortunate) thing all of these couples have in common? Those warnings turned out to be very warranted because none of these relationships ended up going the distance.
Taylor Swift's mom thought she was crazy for dating John Mayer
In the realm of celebrity dating, few people have relationship histories as long — or as talked about — as John Mayer and Taylor Swift. Mayer earned a reputation as a bit of a player after dating a string of famous ladies, including Jennifer Love Hewitt, Jessica Simpson, and Jennifer Aniston, among others. Swift, meanwhile, has built a career penning heartfelt, diary-like confessional love songs — and breakup songs. So, when she and Mayer split after a brief (but intense) relationship, she processed her feelings by writing a song. That song also hinted that someone very close to Swift was against the relationship from the start: her mom.
In her breakup ballad “Dear John,” Swift sings about her mother’s thoughts on her relationship with ex Mayer — and, given the famously autobiographical nature of Tay’s tracks, we can only assume this exchange really happened. “Long were the nights when my days once revolved around you. Counting my footsteps, Praying the floor won’t fall through, again,” the pop star belts out in the song’s first verse before adding, “My mother accused me of losing my mind — but I swore I was fine.” Clearly, this was one instance where the phrase “mother knows best” turned out to be very accurate. Swift and Mayer split in February 2010 after just three months together.
Morrissey warned Katy Perry not to marry Russell Brand
Katy Perry and Russell Brand were one of those celebrity couples that left a lot of people scratching their heads. According to MTV, Perry and Brand connected in September 2009 at the MTV Video Music Awards and married just over a year later, in October 2010. The marriage only lasted 14 months, however, and ended in December 2011 (on New Year’s Eve, to be exact), when Brand infamously delivered the news that he was filing for divorce via text message. “He’s a very smart man, and I was in love with him when I married him,” Perry told Vogue in 2013. “Let’s just say I haven’t heard from him since he texted me saying he was divorcing me December 31, 2011.”
Perry was clearly blindsided by the breakup, but not everyone was so shocked. Before the heartbreak, music legend Morrissey actually warned Katy against the union. “He’s Russell’s mate and he is fascinating but he was giving us a hard time about getting married. He swooned and sighed, ‘Oh, left hand third finger, don’t do it’. It was just so eloquent and poetic and like one of his songs,” Perry told The Sun (via NME). “It would be great to have him at the wedding but I told him, ‘We can’t have a Mr Misery like you messing things up.'”
Did Ariana Grande warn Margaret Qualley about Pete Davidson?
Ariana Grande and Pete Davidson fell fast and hard for each other in 2018, getting engaged after a few short weeks of dating and ultimately splitting after just five months together. The duo got inked with multiple couple’s tattoos and moved into an NYC apartment together during their courtship and Davidson reportedly dropped $100,000 on Grande’s engagement ring. When he confirmed their engagement, Davidson gushed about the relationship, telling Jimmy Fallon, “I feel like I won a contest, it’s so sick.”
After their whirlwind romance ended poorly, Grande reportedly took it upon herself to warn Davidson’s next girlfriend, actress and model Margaret Qualley, to reconsider her own budding relationship with the Saturday Night Live star. “Ariana felt it was her responsibility as a feminist, of course, to warn Margaret about what she was getting herself into,” a source told Life & Style. “She got word to Margaret through a mutual pal, that Pete’s an immature stoner who’d make fun of her on SNL after she eventually dumped him, too.” For what it’s worth, Gossip Cop did report that the rumor that Grande tried to talk Qualley out of dating Davidson was just that — a rumor — but there’s never been a firm confirmation from any of the parties actually involved either way. Still, Davidson and Qualley’s relationship fizzled after just a few months, too.
The Weeknd's ex warned him not to date Selena Gomez
The Weeknd (real name Abel Tesfaye) and Bella Hadid have dated off and on since 2015. During one of those “off” periods, Tesfaye embarked on a relationship with Selena Gomez. Hadid reportedly did not support the relationship, but a friend of the model’s told Us Weekly that Tesfaye ignored his ex’s warnings. “Bella has reached out to Abel a few times and told him Selena is using him,” Hadid’s friend supposedly told the magazine, adding, “He thinks she’s just jealous and isn’t listening to her.”
While there’s no evidence to suggest that Gomez was “using” Tesfaye, Hadid’s instincts about the mismatched pairing turned out to be at least somewhat justified. Tesfaye and Gomez broke up in October 2017 after 10 months of dating. The timing of the breakup coincided with Gomez reconnecting over lunch with her ex, Justin Bieber. “The Weeknd doesn’t think Selena talking to Justin again is weird at all. He doesn’t care,” a source told Us Weekly at the time. The Weeknd stayed mostly silent following the split, but seemed to address it on a few tracks on his album My Dear Melancholy in 2018. “Guess I was just another pit stop, ’til you made up your mind, he sang on ‘Call Out My Name.’ “You just wasted my time.”
Blac Chyna advised a prenup for Kylie Jenner and Tyga
Kylie Jenner’s relationship with rapper Tyga was controversial from its start. According to The Sun, they met in 2011, when Kylie was just 14, and were rumored to have been dating on the down-low for quite a while before her 18th birthday (Tyga is eight years older than Kylie).
In 2015, Tyga’s ex, Blac Chyna, with whom he shares a son, King Cairo, issued a warning to Kylie about the relationship — and it had nothing to do with the age difference. Chyna took to Instagram to send a not-so-subtle bit of advice to the makeup mogul. In a now-deleted video described by Radar Online, Chyna lip-syncs to Drake’s “Back To Back” and “smirks” while mouthing the line, “Shout out to my boss b*tches wifing [expletive]. Make sure you hit him with the prenup.” The post, which came around the same time reports were circulating that Tyga was having money troubles and that Kylie was paying his rent, was widely interpreted as a direct message to the young beauty mogul.
Chyna’s advice, however, turned out to be unnecessary. Kylie and Tyga split in April 2017. About a month later, she started dating Travis Scott, and almost immediately conceived their daughter, Stormi Webster, who was born roughly nine months later, in February 2018.
And then Tyga warned Rob Kardashian about Blac Chyna
Two years after Blac Chyna seemingly took it upon herself to warn Kylie Jenner against tying the knot with Tyga without a prenup, the rapper returned the favor to his ex by privately and publicly warning Jenner’s half-brother, Rob Kardashian, against his own relationship with Chyna. Rob and Chyna started dating in January 2016 and welcomed their daughter, Dream Kardashian, that fall. By the next summer, Tyga went public with his concerns about the union — which he says he shared with Rob before Dream was born.
“I told him what the play was. … This is what you about to deal with,” Tyga explained during an interview on 105.1’s The Breakfast Club, adding, “Chyna, she’s just got a different mentality. She really is a good person at heart, but she’s been through a lot in her life, and she really didn’t have people to help guide her and stuff in her life.” Tyga added that he didn’t think Rob was “gonna be able to handle somebody like her. He coming from a whole different world….He don’t know how she move or how she think. When you’re in love and when you don’t care what nobody else think … love blinds you.” After Rob and Chyna welcomed Dream, though, Tyga backed off. “I told him…but I’m not going to intervene on what they got going on.”
Khloé Kardashian was warned a lot about French Montana
When Khloé Kardashian started dating rapper French Montana back in 2014, she reportedly received multiple warnings about the relationship. Khloé’s family — particularly Kim Kardashian and Caitlyn Jenner — reportedly worried about French early on. “[They] are very skeptical of him,” a KarJenner source told Us Weekly at the time, adding, “They think he’s using Khloé for fame.”
Montana’s ex-wife, Deen Kharbouch, also publicly expressed concerns about the relationship, telling Life & Style: “She has to be careful. Things are not what they seem. … He and I worked together to put him where he is. As soon as he popped, it was as if [our son] Kruz and I didn’t exist. He practically abandoned us. Sometimes we won’t hear from him for two or three months.”
Khloé and French’s relationship fizzled after just a few months, but he insists there’s no bad blood. “I feel like we had a real dope relationship — there was no bad blood, nobody did something to somebody that we couldn’t come back from,” he told Haute Living in 2019, adding, “When the love was like that, it’s always going to be like that. Friendship after a relationship is something that’s real hard to do, and I’m glad we’ve been able to do it.”
Chris Brown's ex warned Kendall Jenner about dating him
There have actually been romantic rumors about Kendall Jenner and Chris Brown twice. In 2014, the pair hung out and a source told Us Weekly that Kendall was “obsessed” with the rapper, who was with Karrueche Tran at the time. Two years later, in 2016, rumors flew that Jenner and Brown might be dating when it was reported that he flew to Paris to spend time with the model during Fashion Week.
By then, Tran was Brown’s ex, and she was most definitely not here for his rumored relationship with Jenner. The actress and model reportedly made a point of slamming Chris to Kendall’s little sister, Kylie Jenner, when she hung out with the youngest KarJenner to film an episode of her YouTube show, Cooking With Kylie.
After speaking with “an insider,” Hollywood Life reported that Karrueche “basically told Kylie to watch out for Kendall and not let her get too close to Chris.” The gossip blog also said the insider claimed that Chris treated Karrueche like a queen — until they slept together. “After that, it was all down hill. Chris is a constant cheater and Kae reminded Kylie that he got a girl pregnant when they were together,” the insider told the outlet, adding, “Kae just wanted to warn Kylie what her sister could potentially be setting herself up for — a lifetime of heartbreak.”
Selena Gomez's friends and family weren't thrilled with this reconciliation
Selena Gomez and Justin Bieber’s romance has been a notoriously tumultuous love affair. They were first linked officially in 2011 and dated off and on for the better part of a decade, reconnecting for the final time in 2017, when Bieber reached out to check on Gomez after her kidney transplant. Even though he only reached out “as a friend,” he and Selena ended up “slowly rekindling their relationship,” a source told Us Weekly, adding, “They have both grown up tremendously and think that this is their time to get back to where they were before, but more in love than ever.”
Still, Gomez’s crew wasn’t totally on board. The Us Weekly source said the singer’s friends worried because she was “in such a good place and so happy without Justin. Her friends want her to be cautious.” Gomez’s friends weren’t the only ones who were concerned about her last go at romance with Bieber. In December 2017, TMZ reported that Gomez’s mom, Mandy Teefey, was so upset about the relationship that she had to be admitted to the hospital. Things between Gomez and her mom were strained throughout the remainder of her relationship with Bieber, which fizzled out again for the final time in early 2018. In January of 2018, Teefey admitted to Gossip Cop that she was “not happy” with the relationship, but added that, “Selena is an adult and can make her own choices.”
A former employee of Jesse James tried to blow the whistle for Sandra Bullock
Sandra Bullock and Jesse James’ five-year marriage broke down in 2010 when it was revealed that James had been habitually unfaithful. That same year, RadarOnline reported that James’ former employee, Deann McClung, who worked for James at West Coast Choppers in Long Beach, Calif., called her former boss “an evil, brutal, terrible person.” The tabloid also cited a separate interview with McClung, conducted in 2005 when Bullock and James were still dating, in which she said, “I’m sure he has Sandra conned into thinking what a nice guy he is, but it’s all a big lie.”
McClung sued James for sexual harassment in 2000 (she and James settled the suit out of court in 2001) and, according to RadarOnline, gave an explosive interview in 2005 that reiterated her allegations. “Jesse James forced me to have sex with him,” she claimed in the interview. “He forced me to have sex, kidnapped me, locked me up and threatened me. He ruined my life.” McClung added, “There was nothing I could do,” while recounting an incident in which she alleges James forced her to perform oral sex on him. “He told me, ‘You wanted this. You know you had it out for me for months.'”
Lindsay Lohan once felt the wrath of a tiger mom
Lindsay Lohan and Samantha Ronson dated off and on in 2008 and 2009, and Ronson’s mom, Ann Dexter-Jones, may have been instrumental in ending the relationship. In 2013, she shared the story of the night that forced her to warn her daughter about continuing a relationship with Lohan. “Suddenly, without any warning, Lindsay flung herself on to the thick carpet and started to roll around screaming like a child. It seemed she was upset that people, including Samantha, were not paying her enough attention,” she told the Daily Mail, adding, “To my mind, it was classic psychotic behaviour. I took Lindsay aside and told her not to make a spectacle of herself. She was clearly out of control and spoiling for a fight.”
After that incident, Dexter-Jones decided it was time to let Ronson (and Lohan — awkward) know she was officially throwing a warning flag on the relationship. “The http://wp.looper.com/wp-admin/admin.php?page=nggallery-submissions&a=40753#morning after her tantrum — and believe me, that was not the worst of it — I told them both that I could no longer support them as a couple, that I no longer approved of them being together and that Lindsay was no longer welcome in my home.” Ronson later concurred with her mom, telling the Daily Beast that the relationship was “not healthy.”
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