Sienna Miller and Jude Law
Read more: Other stars who had affairs with the help— and got caught
Big Sean and Naya Rivera
Oh, the drama. It took all of a year for the Glee actress and the rapper to meet, get engaged, then break things off. But unlike these celebrity couples, their split was anything but amicable. There were reports that he was unfaithful, and she tweeted — then deleted — something about him "stealing Rolexes" because she is "on Glee and making more money or something." Ouch. The final straw? The exes unfollowing each other on Twitter. #toobadsosad
Brad Pitt and Gwyneth Paltrow
Their matching haircuts wasn’t enough for the golden couple. Paltrow seemed rarin' to get hitched but she later said that she wasn't at all ready for marriage and kids and admitted she was a "big mess." Our only question: Would the world still have hated Goop if she married Pitt? Probably.
Evan Rachel Wood and Marilyn Manson
The rocker proposed while on stage in Paris and she happily accepted. Eight months later, they called the whole thing off. Their age gap — he was 39 at the time of their engagement; she was 21 — seemed like the obvous reason for their split but it may have simply been an impulsive decision that was re-examined.
Johnny Depp and Winona Ryder
The love they found on the set of Edward Scissorhands wasn't enough and their decision to get married no longer seemed right. Plus, Ryder was 19 when they got engaged; perhaps too hasty for someone that young? Turned out, Winona wasn't forever.
Kelly Osbourne and Matthew Mosshart
Perhaps Osbourne is a bit of a commitmentphobe as she has two broken engagements under her belt. The first was from Luke Worrall in 2010, and she called it quits with Matthew Mosshart earlier this year.
Jennifer Lopez and Ben Affleck
Before the days of social media, there was the original Bennifer. Their relationship was epic and when Affleck gave J.Lo that pink diamond engagement ring ($1.2 million, 6.1 carat, FYI), we were all prepared for a lifetime (or at least a couple of years) of gossipy goodness. They even set a wedding date but ended up postponing the nups mere days before they were set to exchange "I dos" — and broke up for good shortly afterward.
Jas Prince and Christina Milian
The singer and CEO of Rap-A-Lot Records had been engaged for over a year when they decided to end their relationship. And what better way to do it than with a cryptic post on Instagram? First, Milian captioned a photo of herself cuddling with her newborn niece with "rough day," as well as an inspirational message: "There comes a time in life, when you walk away from all the drama and people who create it." Prince also took to social media, writing, "Keep calm, pray and leave it all in God's hands."
Sheryl Crow and Lance Armstrong
The disgraced cyclist began dating Crow shortly after he filed for divorce from his first wife. Hmm. Two years later, they were engaged but five months after the proposal, they announced to the world that they were better off apart. "After much thought and consideration we have made a very tough decision to split up. We both have a deep love and respect for each other and we ask that everyone respect our privacy during this very difficult time." The lesson here?
Jesse James and Kat Von D
Alanis Morrisette and Ryan Reynolds
We'd take this Canadian couple over Avril and Chad any day but, alas, it wasn’t meant to be. Their nearly three-year-long engagement probably didn't help but the pair did break up with class in this lovely statement: "They remain close friends and continue to have the utmost love and admiration for each other. They ask that their privacy be respected surrounding this personal matter."
Katie Holmes and Chris Klein
These two were kind of adorable together, no? And she looked happy and healthy and didn't sport the dead eyes she had throughout her marriage to Tom Cruise. Holmes and Klein were together for five years but a two-year engagement is almost never a good sign and they ended things two years after his proposal.
Julia Roberts and Kiefer Sutherland
This was one of the most scandalous splits ever. Just three days before the Flatliners stars were scheduled to marry, she ran off with his best friend, Jason Patric. Sutherland could've remained bitter towards Roberts but a decade later, he said of his runaway bride-to-be, "I commend Julia for seeing how young and silly we were, even as painful and difficult as it was." Classy.