Love may have abounded at the 2019 Academy Awards, but less than two months into the year, 2019 was already shaping up to be just as rough as 2018 in the realm of celebrity relationships—or perhaps even more so, if Khloé Kardashian and Tristan Thompson are any indication. (The couple managed to weather an ultra-public cheating scandal last year, even while juggling the birth of their newborn, though Thompson turned out to be pushing his luck when he cheated on Kardashian once again.) Bradley Cooper and Irina Shayk, on the other hand, have tried to keep their four-year relationship as private as possible, though that didn’t stop the news from getting out when they reportedly broke up in June. Still, there’s a bit of good news to be found amid all the heartbreak: MacKenzie Bezos decided to make the best out of the end of her 25-year marriage to Amazon’s Jeff Bezos, aka the wealthiest man in the world, by donating half of her post-divorce $37 billion fortune to charity. Pay your respects to those couples and the rest that 2019 has claimed so far here.
BRADLEY COOPER AND IRINA SHAYK Bradley Cooper and Irina Shayk have done their best to keep their relationship private since they began dating four years ago, over the course of which Shayk gave birth to their daughter, who’s now two. In June, however, People reported that the pair has split—a turn of events that tabloids (and fans of A Star Is Born, which Cooper directed and starred in opposite Lady Gaga) have been predicting for months.
HENRI LEVY AND DEMI LOVATO Demi Lovato has largely been staying out of the spotlight since she overdosed last summer, but in the past few months, she’s begun returning to the public eye, often in the company of Henri Levy, designer of the label Enfants Riches Déprimés. After four months of dating, which saw Lovato give Levy a puppy for Valentine’s Day, though, the pair has reportedly split.
LILY ALLEN AND MERIDIAN DAN Lily Allen’s breakup with Meridian Dan, a grime MC from North London, not only marked the end of their three-year relationship but also, according to Allen, marked the first time she’s been single since she was 15.
METIN HARA AND ADRIANA LIMA Adriana Lima has been making quite a few life changes as of late: The past few months have seen her both officially retire from the Victoria’s Secret Fashion Show and publicly make the decision to only take her clothes off if there’s a cause involved. In January, it turned out those changes had carried over to her personal life, too, following the announcement of her split from the Turkish writer and self-help guru Metin Hara, whom she’d been dating for the past year and a half. Her marriage to herself, on the other hand, appears to remain intact.
MILES MCMILLAN AND ZACHARY QUINTO Two days after they ominously attended two different post-Oscars parties, news broke that the 41-year-old actor Zachary Quinto and the 29-year-old artist-slash-model Miles McMillan are no longer an item. Before that they’d been dating for nearly six years.
RITA ORA AND ANDREW GARFIELD If you didn’t know that Rita Ora and Andrew Garfield were reportedly dating, you’re not alone. In any case, it’s apparently already in the past; their relationship, which seems to have begun in November, has “fizzled out,” according to the tabloids, which seem to have been the only ones aware of it in the first place.
SHANINA SHAIK AND DJ RUCKUS Shanina Shaik and DJ Ruckus announced their separation in June, a year after they got married on a private island owned by Lenny Kravitz.
SHAYNA TAYLOR AND RYAN SEACREST For the second time in five years, 44-year-old Ryan Seacrest and 26-year-old Shayna Taylor, who defended the E! host when he was accused of sexual misconduct, have parted ways.
TRISTAN THOMPSON AND KHLOÉ KARDASHIAN It took two public cheating scandals for 27-year-old Tristan Thompson and 34-year-old Khloé Kardashian to part ways. Less than a year after the first, which broke practically at the moment that Kardashian was giving back to their daughter, True, Thompson’s alleged infidelity again returned to the spotlight. (This latest instance is unfortunately even messier, involving the Kardashians’ 21-year-old comrade Jordyn Woods.)
BELLA THORNE AND TANA MONGEAU Bella Thorne and the YouTube star Tana Mongeau announced that their year-long open relationship had come to an end on Twitter, with the latter noting that she will “love [Thorne] forever.”
BELLA THORNE AND MOD SUN In just a few short months, Bella Thorne has gone through not just one but two breakups this year. Two months after ending things with her ex-girlfriend Tana Mongeau in February, Thorne split from Mod Sun, her boyfriend of a year. The breakup appears to be amicable, though, as Thorne shared a selfie with the rapper on Instagram, along with the caption, “I will always love you. All good things must come to an end.”
ALEX GREENWALD AND BRIE LARSON Ten years after his band, Phantom Planet, became forever associated with the unforgettable theme song for The O.C., lead singer Alex Greenwald began dating the actress Brie Larson. It wasn’t long before she gave him a shout-out in her Oscar acceptance speech and they got engaged, but unfortunately, not all things last forever: While they reportedly “remain close,” the couple has since called things off.