There are roughly three varieties of celebrity breakup. First, you have your conscious uncouplings, civil partings announced in publicist-penned essays filled with vows to remain friends and/or loving co-parents. This type of split is followed by polite silence, or, more rarely, genuine-seeming amity. Then, there are the bitter breakups, where there appears to be nothing but acrimony on both sides (see Brad Pitt and Angelina Jolie’s divorce, which is currently in its 5th year). Finally, we’ve got the lopsided heartbreaks, in which half of the couple appears to have moved on, while the other half seems determined to go down with the ship of their one-time romance. (We’re not talking about breakups that result in genuinely troubling behavior—think corny love songs, not long-term harassment.)
These days, the celebrities who have the hardest time letting go are often the ex-boyfriends and husbands of some of the most celebrated women on the planet. Anyone can see that it would be tough to watch Jennifer Lopez or Rihanna walk out of your life. But have some pride! Getting dumped is no excuse to embarrass your ex, or to make us, the captive spectators of your love life, want to cringe our faces off.
2 / 9
Mr. Cannon wants that old thang back. You know you’ve got that good-good when your ex-husband writes a song about missing you six years after your divorce. On Feb 15th, Nick Cannon’s released his dedication to Ms. Carey, entitled, “Alone.” Auntie Mariah indeed has the bedazzled juice and 7-carat sauce and has left our poor brother Cannon cold and alone. Any rom-com connoisseur will tell you that when an ex publicly confesses love through a serenade, it’s real.
“I’d been lyin’ / I say I’m cool when I know I miss it,” he belts. “I’d trade it all for the case / If I could have you back / If I could go back to where we started at.”
Despite Cannon now having five baby mommas and seven children, it’s Mariah who still has Cannon in his feelings. It’s been years since their divorce—fans want to know: what prompted this song now? Maybe the life of countless women that Cannon so proudly flaunts isn’t the glamorous life he thought it would be. Perhaps his sheets were cold on VDay and Carey’s empty side of the bed brought up thoughts of settling down for the perpetual bachelor... –Khalisa Rae Thompson
3 / 9
Lamar Odom is no stranger to the concept of getting entangled in a web of scandal, as proven by the many troubles that have plagued the ex-Laker throughout his uneven career and stormy 7-year marriage to none other than Khloe Kardashian.
The once lovey-dovey couple were married from 2009-2016, conveniently during the height of Lamar’s golden days as a Laker. Lamar’s appearances on “Keeping Up With The Kardashians” led to one of many spinoffs, “Khloe and Lamar” that showcased the couple in their element. But once Lamar’s days as a prized Laker on a championship team came to an end, and he was downgraded to the Dallas Mavericks, the celebrated couple’s love connection fizzled.
Lamar’s rampant infidelity and public battle with drug addiction certainly didn’t help matters, and despite how awful it got with a well-publicized near-fatal overdose at a Nevada brothel in 2015, his faithful wife famously never left his side and continued to selflessly cater to the urgent needs of her estranged husband fighting for his life.
That likely explains why all these years later, Lamar Odom is still unable to close the chapter on a doomed love story that shouldn’t be revived under any circumstances. The trolling is constant from the hovering ex-husband who not only lavished praise on his ex-wife in his 2019 memoir “Darkness to Light,” but also dedicated the book to her, while professing his undying love as if his second chance was waiting in the wings.
Lamar’s trolling also extends to NBA star and Khloe’s biggest mistake, Tristan Thompson, who was recently forced to claim his unborn child conceived from a one-night stand. TMZ caught up with Lamar to get his reaction to his former wife’s woes and he didn’t hold back, “Dude was corny for that, but it’s all good.” Well, it takes one to know one!
His latest gig as a housemate on “Celebrity Big Brother” made headlines after he expressed regret about how his marriage to Khloe imploded for the world to see, “I didn’t treat that woman right, I’m going to try my damndest to reconnect with her.” But then he ends his confession with the realization that he’s probably not going to get what he desires, “She has the right to never ever want to see me again for the things I put her through, but time moves on and people change.”
Frankly, we are rooting for the permanent demise of Khloe and Lamar with only the occasional TV reruns to serve as evidence of how “moving on and changing” is the best revenge. –Ezinne Ukoha
4 / 9
Bennifer 2.0 has been so omnipresent that it’s easy to forget that immediately before Jennifer Lopez rekindled her romance with Ben Affleck and helped usher in the early aughts revival, she was attached to another famous man, Alex Rodriguez.
Despite rumors that the pairing collapsed amid allegations that he’d cheated, A-Rod didn’t take the end of their five-year-long relationship well. Instead, he posted a video to his Instagram stories in which he silently filmed photos of himself and Lopez, along with a framed picture of their names written in a heart in the sand. Rodriguez himself didn’t speak a word, and instead decided to let Coldplay do the talking, as their weepy anthem “Fix You” played in the background. Looking at old photos while listening to sad songs—we’ve all been there. Recording that sad sack garbage posting it to social media, and tagging your ex? A pathetic bridge too far. –Gabrielle Bruney
5 / 9
From 2006 to 2016, Scott Disick and Kourtney Kardashian shared a turbulent, on-again-off-again relationship that yielded three children, and no shortage of drama for Keeping Up With the Kardashians. Now, after years of putting up with Scott’s frequent affairs and relationships with barely legal models, and other assorted bullshit, she’s happily in love with and engaged to Blink-182 drummer Travis Barker. Disick quite obviously can’t stand it.
Last summer, another of Kourtney’s exes, Younes Bendjima, exposed Disick for sending him a DM expressing disgust with Barker and Kourtney’s relationship: “Yo is this chick ok!???? Broooo like what is this. In the middle of Italy,” Disick wrote, referring to Kourtney’s numerous Instagram posts featuring her and Barker publicly making out whilst on a romantic vacation. One source has said Disick “never approved of Kourtney dating Travis,” and “has struggled with their relationship” because he always believed “he and Kourtney would eventually get back together.” By all accounts, Disick, like others in his cohort of men who have fumbled hot celebrity women, seems to be down bad, and he has no one to blame but himself.–Kylie Cheung
6 / 9
The month of Black love seems to have a few men in hip-hop shook, clutching pearls and old wallet photos, reminiscing about the one that got away. Drake is among the squad of broken-hearted romantics this February. Upon learning that Rihanna and ASAP Rocky were expecting a baby, he went straight to the unfollow button on both Twitter and Instagram like the petty Champagne Papi we knew him to be. However one-sided and short-lived his 2016 public love confession and “relationship” with Rihanna was, the memes and Twitter jokes were just the opposite. Within a matter of minutes of Drake pressing that little blue button, Twitter flocked to their meme-makers and used their 140 characters to roast our precious albeit broken-hearted Drizzy. All in good fun, our minds fill in the blanks. We created hilarious scenes of Drake in his silk pajamas playing their 2016 duet, “I’m Too Good To You” and Mint Condition’s “Breakin’ My Heart,” sipping Private Stock, letting one tear roll down his freshly exfoliated cheek.
While Ms. Fenty is embarking on a new chapter, Drake seems to cling to a past of duets, friendly hangouts, and what could have been. One can only shake their head and feel sorry for the homie; Pop Crews photographed him visiting all of Rihanna’s favorite childhood spots in Barbados back in 2020 for what his team says was “album prep.” Twitter posts reported him cuddling up with her family members, but all the true players know the truth— wounded hearts heal best when they’ve got time to reflect on those Fenty pheromones under a tropical sky with nothing but a piña colada and sand to heal his heart. Rih has moved on. The question is: will Aubrey?–Khalisa Rae Thompson
7 / 9
When Hilary Duff’s Lizzie kissed Aaron Carter under the mistletoe on a 2001 episode of Lizzie McGuire, the earth may as well have shaken beneath my very feet. That the two 13-year-olds went on to a real life relationship also felt like a very big deal to my grade school self, as did the rumored love triangle that resulted when Carter later dated fellow child star Lindsay Lohan. Still, I was pretty much over the whole thing by 2014 —as was Duff, who’d married and had a kid with a different man. You know who wasn’t over it? Carter. That year, he began tweeting about their decade-old courtship, sending off messages like, “I’ll spend the rest of my life trying to better myself to get back to her. I don’t care what ANY of you think,” and, “Don’t be that stupid douche that loses the love of your life forever.. Like me…”
Duff, who was probably busy doing stuff like filming Younger and raising her kid, was understandably put off. “I don’t know what to say about it! It was so many years ago,” she told Andy Cohen at the time. “It’s uncomfortable.”
“He was very sweet,” she added, “when I was 13.”—Gabrielle Bruney
8 / 9
Justin Bieber is now music’s premier wife guy, but this wasn’t always the case. Between 2011 and 2014, he dated Selena Gomez, and the pair were the Brangelina of the tween set. After their breakup, he created an extraordinarily embarrassing Instagram post, one that, unlike most of the social media groveling in this slideshow, is still standing today. It was a photo of Gomez at that year’s Vanity Fair Oscars party, and he captioned it simply, “Most elegant princess in the world.”
As far as post-breakup courtship goes, it was relatively dignified. No out-and-out begging, just a single, sappy sentence. Gomez’s response was similarly restrained. She posted a picture of herself with Vanessa Hudgens, and judging by the dress, it was taken at the very same Vanity Fair shindig. The caption read: “my only, official party buddy for life,” which was pretty polite for a stern brush-off. —Gabrielle Bruney