As much fun as it is to follow along with celebrity weddings, where the real intrigue is at is celebrity engagements. Many stars have been married multiple times, but some celebrities have pretty impressive diamond ring collections that never ended up leading them down the aisle — and in some cases, the weddings were already planned and ready to go before the couple decided that it was best to go their separate ways.
Honestly, these broken engagements are ultimately a good thing — it's way better to figure out if a marriage isn't going to work before actually tying the knot, so good for these stars for being able to make the hard decision to walk away from a relationship that isn't working. Breakups are difficult enough without having to go through them while living in the spotlight, after all!
Read on for all the stars who have been engaged more than once. Some of these engagements led to marriages, while others didn't — but if they had, the landscape of couples in Hollywood might look a whole lot different today.
Drew Barrymore
Though Drew Barrymore has been married three times — to Jeremy Thomas, Tom Green, and Will Kopelman, in that order — she's been engaged two other times, too. Her first was at the age of 16 to Leland Hayward, the grandson of the Hollywood producer of the same name, and then a year later, she dated and was engaged to Jamie Walters, though their relationship was short-lived.
Jennifer Lopez
Jennifer Lopez definitely has one of the most impressive engagement records in the game. In total, J.Lo has been engaged five times — to Ojani Noa, who she was married to for less than a year; Cris Judd, who she was only married to for nine months; Ben Affleck, who she never ended up marrying; Marc Anthony, her ex-husband of 10 years; and Alex Rodriguez, her latest official relationship that ended in early 2021.
Paris Hilton
Paris Hilton also exists among the ranks of Hollywood women who have had multiple engagements. Although the heiress has been engaged four times, she's never actually been married. In the past, she's received rings from ex-boyfriends Jason Shaw, Stavros Niarchos, and Chris Zylka, and currently, she's engaged to Carter Reum.
Demi Moore
Though Demi Moore counts Bruce Willis and Ashton Kutcher among her ex-husbands, before her marriages to either of those men, she was engaged to Emilio Estevez after they met and fell in love on the set of St. Elmo's Fire. According to Cheat Sheet, Demi wrote in her memoir that she broke things off after she found out that Emilio had cheated on her.
Lady Gaga
So far, Lady Gaga (real name: Stephanie Germanotta) has never actually made it down the aisle, but she's been proposed to a time or two. She's been engaged to both Taylor Kinney and Christian Carino, though neither of those engagements turned into marriages. Today, Gaga is dating Michael Polansky — maybe another ring is in her future?
Ariana Grande
In May 2021, Ariana Grande tied the knot in a small ceremony at home with real estate agent Dalton Gomez, but that wasn't the first time she'd been engaged. Previously, Ariana was planning to marry comedian Pete Davidson, but their whirlwind romance quickly came to an end in 2018.
Gwyneth Paltrow
Today, Gwyneth Paltrow is married to producer Brad Falchuk, following her divorce (or "conscious uncoupling") from Coldplay frontman Chris Martin. But before her relationships with either of them, Gwyneth was engaged to fellow actor Brad Pitt, whom she dated for three years in the '90s but never actually married.
Brad Pitt
While we're on the topic of Brad Pitt, we all know that he's famously been married to (and divorced from) Jennifer Aniston and Angelina Jolie, and we can add Gwyneth to his list of ex-fiancées. But Brad has also been engaged to Jill Schoelen, way back before his more high-profile romances.
Kate Hudson
Though Kate Hudson is happily enjoying her relationship with Danny Fujikawa these days — and he hasn't yet popped the question, as far as we know — she's been married and engaged before. Kate was formerly married to Chris Robinson of The Black Crowes, and she ended her engagement to Matt Bellamy before they ever made it to the altar.
Julia Roberts
Julia Roberts has been married to Danny Moder since 2002, and before that, she was wed to Lyle Lovett for two years in the early '90s. But the rom-com icon has also been engaged to Keifer Sutherland (she called off the wedding just days before it was all supposed to go down) and Dylan McDermott.
Mariah Carey
Along with her marriages to Tommy Mottola and Nick Cannon, Mariah Carey was also engaged a third time to billionaire James Packer. It doesn't seem like that was an important relationship to the singer, though; in an interview with the Guardian, she said that James didn't make it into her memoir because she only included relationships that mattered. Ouch!
Ryan Reynolds
At this point, it's hard to imagine Ryan Reynolds married to anyone but Blake Lively, but it's happened before. Not only was he married to Scarlett Johansson, but before that, he had a high-profile relationship and engagement to singer Alanis Morissette, though they never made it to their wedding day.
Johnny Depp
Johnny Depp has reportedly been engaged a whopping six times, though he's only been married twice — to Amber Heard and Lori Anne Allison. He's also been engaged to Sherilyn Fenn, Jennifer Grey, and Winona Ryder, with speculation that he might have been engaged to longtime love Vanessa Paradis (who also happens to be the mother of his children). Johnny and Vanessa were together for 14 years.
Danielle Staub
Real Housewives of New Jersey star Danielle Staub might be going for some kind of record. She's been married three times: to Kevin Maher, Marty Caffrey, and Thomas Staub. But her engagements? Well, she's been engaged a total of 21 times, including those marriages. Whoa!
Kim Kardashian
Kim Kardashian has received three engagement rings from three husbands: Damon Thomas, who she was briefly married to at just 19 years old, Kris Humphries, to whom she was famously only married for 72 days, and Kanye West, her third husband, who is about to become her ex.
