14 Celebrity Engagements That Went Sideways
Seth Rogen had the most Seth Rogen engagement you can imagine.
Johnny Depp
Ever the romantic, he didn’t bother to get Amber Heard’s finger measurements before he went out and got a ring. He wound up just adding it to his own jewelry collection: “I have a female engagement ring. It was too big for my girl.”
Sienna Miller and Jude Law
They tried and failed twice, but their first breakup was the juiciest. After a two-year engagement, Sienna found out that Jude had had an affair with their kids’ nanny.
Katie Holmes and Chris Klein
The two dated for five years, and were engaged for two years after that. Just a handful of months after the engagement was called off, Holmes was dating Tom Cruise, leading people to suspect she was being vetted as the potential next queen of Scientology during her original engagement.
Peter Facinelli
He hired a plane to fly by the Empire State Building with a “Will You Marry Me?” banner at 4 p.m., got his girlfriend up to the observation deck… where she decided she was too cold and insisted on going inside at 3:55 p.m.
Ariana Grande and Pete Davidson
Within one month of their first date, the two moved in together, got couples tattoos and got engaged. Somehow, all that mutual lovebombing didn’t translate to a stable relationship, and the engagement was briskly called off. But the dust from their torrid love affair took a long time to settle — Grande had already recorded her album Sweetener, which featured a track called “Pete Davidson” and reportedly almost had a Davidson rap on it.
LL Cool J
He improv’d an extremely unromantic proposal — without a plan or a ring, he leaned over to Simone Smith while he was driving and said, “Do you wanna do this?”
Cynthia Bailey
Fellow Real Housewife Kenya Moore had gotten advance notice that Bailey’s boyfriend was going to propose, and was physically incapable of playing it cool, telling her earlier in the day, “I feel like he might propose tonight!”
George Clooney
After winning a $10,000 bet with Michelle Pfeiffer and Nicole Kidman that he’d stay a bachelor until 40, he eventually settled down with Amal Alamuddin — after his proposal turned into a half-hour long negotiation.
Megan Fox
After Brian Austin Green proposed on a Hawaiian beach, onlookers say Fox dropped the ring in the sand: “I saw her jumping up and down. Later, I saw a half dozen staff sifting through the sand.”
Ryan Reynolds and Alanis Morissette
The two were engaged for three whole years before they called it off. On the surface, everything was cordial, thanks to a masterclass in PR niceties. But Alanis later admitted that her 2008 album Flavors of Entanglement was an act of “catharsis” written entirely about Reynolds and their breakup.
Seth Rogen
He had big romantic plans, but when he got the ring he felt compelled to rush upstairs and pop the question: “She was in our closet changing, and she was literally only in her underwear and her boobs were out. I figured the only appropriate thing was to place the ring on her nipple actually.”
Howard Stern
He got his girlfriend naked on purpose, telling her he had a gift for her, but she could only have it if she was naked. Upon undressing, she found it was a 5.2-karat ring.
Robert Pattinson and FKA Twigs
T-Pain, of all people, announced the news of the couple’s engagement before they were ready to alert the press: “And she’s engaged now, so that’s about to be a whole other thing… to ol’ Patty. I don’t know if she wanted anybody to know that.” He tried playing it off like it was an April Fool’s joke, to no avail.
Julia Roberts and Kiefer Sutherland
The two got engaged in 1990, but called it off three days before the wedding, which was to be held on a movie sound stage decked out to look like a lavish garden. Soon after, Roberts went on a romantic trip to Ireland with Sutherland’s best friend, Jason Patric, and they dated for about a year.