14 Ex-Celeb Couples Who Called Off Engagements
Celebrity breakups can be sad, messy, and straight-up chaotic. But celebrity engagement breakups? That's next-level tragic.
These 14 couples were thissss close to tying the knot, but never made it to the altar. Here are some of the most iconic, surprising, and totally unexpected celeb pairs who almost said 'I do'...then didn't:
Lady Gaga and Taylor Kinney
These two first crossed paths on the set of Gaga's "Yoü And I" music video — the one with mermaids, electrocution, and Gaga kissing herself? Yes, that one. In 2015, Kinney popped the question on Valentine's Day with a heart-shaped ring. The pair split the following year due to the all-too-familiar 'long-distance and complicated schedules.'
Julia Roberts and Kiefer Sutherland
Talk about a wedding disaster. Julia Roberts and Kiefer Sutherland got engaged in 1990, but broke up just three days before the wedding. The twist? Julia hopped on a plane to Ireland with Kiefer's best friend, Jason Patric. Yes, really. Peak tabloid era insanity.
Ryan Reynolds and Alanis Morissette
This Canadian power couple was engaged from 2004 to 2007, and are one of the more unexpected pairings in pop culture history. They announced their separation in 2007 with zero drama, but Morissette later gave us a few emotional tracks fans suspect are about him on her album Flavors of Entanglement.
Ariana Grande and Pete Davidson
Remember 2018? The year of 'God is a woman,' and a pop culture fever dream of an engagement. The two started dating, got tattoos for each other, moved in together, and got engaged all within one month. Then, just as quickly as it started, it was over. It was chaotic, and gave us Sweetener, so honestly…no notes.
Katie Holmes and Chris Klein
Before there was Tom and Katie, there was Katie and Chris. The pair got engaged in 2003 after five years of dating, but quietly called it off in early 2005. A few months later, Katie was dating you-know-who (Tom Cruise, in case you hadn't figured that one out yet).
Demi Lovato and Max Ehrich
Quarantine relationships move fast — and wow, did this one fly. Demi Lovato and Max Ehrich were briefly engaged in July 2020 after a few months of dating, complete with a romantic Malibu beach proposal. By September it was over...very publicly. Max went on social media rants, and Demi announced she wanted "nothing to do with him." What beautiful tragedies lockdown brought us.
Gwyneth Paltrow and Brad Pitt
These '90s icons began dating after playing lovers in the crime thriller Seven — and yeah, we all know how that one ended. They eventually got engaged in 1996, but called it off just a year later. Still, no bad blood! Gwyneth later said she was 'not ready' for marriage at the time.
Channing Tatum and Zoë Kravitz
One of the more recent (and tragic) heartbreaks on this list. This impossibly attractive duo got together after working on Blink Twice in 2021, and by 2023, Zoë was spotted with a ring on her finger. While they never confirmed the proposal publicly, sources said wedding plans were underway. But by early 2024, it was the end for Tatum and Kravitz — and yes, Channing has already moved on.
Ben Affleck and Jennifer Lopez
Ah, the original Bennifer. They postponed their 2003 wedding due to 'excessive media attention,' only to call it off entirely. Then came the plot twist: nearly 20 years later, they reunited, and actually married in 2022. Buttttttt then…they split again, with an official divorce! Is this really the end of Bennifer? Only time can tell.
Sienna Miller and Jude Law
Sienna Miller and Jude Law were everyone's fav 'it' couple of the early 2000s. They got engaged on Christmas Day in 2004, but things fell apart in 2006 after a huge scandal involving Jude and his kids' nanny. They tried again in 2009, but eventually ended things for good. A holiday engagement, a nanny affair, a reunion, and a dramatic downfall — this one had it all.
Rachel Bilson and Hayden Christensen
This millennial dream couple first met on the set of Jumper in 2007 and got engaged the next year. After a brief breakup in 2010, they reunited and even had a daughter together. But by 2017, it was officially over. RIP to Anakin Skywalker and Summer Roberts.
Mark Ronson and Rashida Jones
Music legend + TV legend = a very cool couple that didn't quite make it down the aisle. Mark proposed in 2003, but the engagement fizzled out about a year later.
Sandra Bullock and Tate Donovan
Before she was America's sweetheart, Sandra Bullock was engaged to her Love Potion No.9 co-star Tate Donovan. They dated for about three years in the '90s and even got engaged — but called it off before saying their 'I do's.' A true rom-com that didn't get its happy ending.
Zayn Malik and Perrie Edwards
These two met on The X Factor, got engaged in 2013, and broke up two years later. Initially, there was a rumour the breakup happened over text, but Zayn denied it. The breakup was very public, and kinda iconic…mostly because fans suspect it inspired some of Little Mix's absolute best songs.
Did we miss any big heartbreaks? Got thoughts on these iconic couples? Let us know in the comments below!
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He was a pioneer in carving out a new Deep South concert scene, billing these rock shows as 'dances' because, as Mom explained, going to concerts back then wasn't yet accepted in the buttoned-down Bible Belt. Not once did Dad talk about this to me. I wondered if he was secretly ashamed that his dreams had deflated into owning a company that supplied concerts with tents, tables and chairs instead of attention-grabbing talent — a company that started from the leftovers of those rosy rock days, with an old red-and-yellow tent top Richard put up over the stage for his acts. 'Where did you find this?' I asked Mom. She waved me down the grungy, carpeted stairs to the basement, where a battered tank of a file cabinet stood tucked away in a nook. As a kid, I'd overlooked it a million times, more captivated by the toys and board games surrounding the 1940s-era metal tower. Opening a squeaking drawer, I saw it fully packed with documents, an extremely thorough paper archive focusing on Dad's time as a concert promoter from 1968 to 1976. He'd saved it all: contracts, guest passes, flyers and posters, ledgers, photos, receipts (sometimes scrawled on a bar napkin). Bathed in the sickly, fluorescent basement lights, I was overwhelmed by the gravity of these to do with all this? Back upstairs, Mom and I discussed selling some ofthe hoard. Dad had saved many copies. But I was hesitant. 'Some items should be off-limits,' I said. Out of respect for Dad, for his story, for this side of him I didn't know. Mom agreed. So we went through each document of Dad's old music promotion business, Peace Concerts. I read the print too tiny for Mom's eyes and wrote descriptions while she priced and categorized. For an eye-catcher, we chose a silvery, vintage poster of a bare-chested Stevie Nicks and Lindsey Buckingham when they were still a dad had booked the last concerts they did before joining Fleetwood Mac and made a bundle on those few shows. The pair were treated so well that Nicks later said in an interview: 'We could join Fleetwood Mac or we could move to Birmingham, Alabama.' Mom and I decided we would not part with the poster. However, we did make glossy reproductions and sell them for $20 a pop. On a too-brightspring day about a year after Richard's passing, I packed my mom's car with the rock files anddrove us to our first record show at a modern, red-bricked convention center. Set up in a large room by plate glass windows, we sold 'retro musical mementos' mostly to old rock 'n' rollers and longhaired hippie-looking characters, all grizzled or gray now, some with a limp or cane. Yet when they browsed the faded posters and dog-eared flyers, a smile would break across their faces as they remembered that packed after-party my dad threw for Stevie and Lindseyfor their sold-out show at the Alabama Theater, the last concert they played before merging with Fleetwood Mac —or how everyone's ears were ringing after that raucous Lynyrd Skynyrd concert at Rickwood Field in '74, the first time that group performed 'Sweet Home Alabama' in the state. For this generation, music was a spiritual experience, and my dad was at the center of it. Well, center backstage. I fidgeted in my chair as I nodded along, jealous that it seemed like these strangers knew my father better than I did. Occasionally, one would squint at meand say, 'You look just like him.' It's true. I have my dad's red-brown curls and intense blue eyes. Although I always thought his shade of eggshell blue was far prettier. Music was another thing we had in common. Dad possessed a sweeter voice, but I was the better guitarist. I didn't start learning until I was 16, so he never played music with me nor expressed an interest after the depression sank deep inside him. Years into his isolation, I visited to perform for him. I must've been 20 and studying classical guitar, eager to show off my new finger-style skills. But after I finished my first piece, a difficult and delicate arpeggiated prelude by a Paraguayan composer named Barrios, he snapped at me, 'That's good, andI won't even count those two mistakes you made.' My throat clenched —my voice evaporated. His ear was still so sensitive. It wasn't a spotless performance, as he'd demanded of his local bands back in the Peace Concert days — he'd told my mother how he kept detailed, sometimes harsh, performance notes from his spot in the back row. I wanted to snap all my guitar strings. Instead, I never played for him again. For years, a feeling of shame flooded over me when I flashed back to that memory — and I carried my resentment around inside like a balled-up mass of old strings. So it went at the record shows: After selling for several hours, Mom and I would gingerly repackage everything back into her car, and I'd drive us back home. We'd split the cash, and I'd roll us a joint. 'For Richard,' we'd toast as thick blue smoke unfurledaround our heads. 'Did he hang out with the acts other than just working with them?' I asked. Mom bit her lip and thought about it. Long ago, Richard told my mom some of Peace Concerts' history — how he saved money from his job at the telephone company to book his first acts, and how promoting was like gambling and he lost it all on a bad run of concerts where the ticket sales didn't materialize. 'Not really,' Mom said. 'He wasn't in it for that. He liked making money — and he did it for the thrill.' 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She said he hated old concertgoers wanting to wax nostalgic with him about the glory days.I figured Dad, like me,always had big dreams hounding him down. Time spins like a vinyl, and after doing a few of these record shows and hearing every tale Mom knew, I began reaching out to Dad'sold friends and work associates from his promoting prime. Yet I heard the same thing I already knew: Dad was a 'workaholic.' 'And how exactly did he fall out of promoting?' About this I'd heard different stories. Mom had always said he'd lost it all on a bad concert run with Joe Cocker, and that he was distracted chasing a woman nicknamed 'Little Red' who never reciprocated my father's interest. But I'd heard more than one old associate say that Dad had also been outgunned by a hotshot New York promoter namedTony Ruffino who today gets the credit for putting Birmingham on the map for big rock bands. One old rock buddy who used to hang up flyers and do other promotional work even said that Richard tried to go rogue and represent Lindsey Buckingham and Stevie Nicks on his own, and for this the record biz blacklisted him. 'But what was he like as a person?' I'd ask these strangers who knew 'the old Richard.' That was always harder for them to answer. 'He was a private guy,' was the best answer I got from a man named Wendell, a partner in an early booking agency my dad founded and later sold. 'He didn't talk much about what was going on in his head.' I became desperate, looking to our family albums and VHS tapes for answers. But here, too, Dad was the invisible promoter, so frequently on the other side of the camera capturing/directing holidays and trips instead of being in them. A backstage man, even in his personal life. Wendell suggested I visit the iconic 2121 high-rise in downtown Birmingham to see my father's old office, where he built his Peace Concerts empire nearly six decades ago in what was then called 'the penthouse,' room 1727. When I told Mom about the idea, she smiled and said Richard used to point out the 2121 building in their earlier days, telling her he worked at the top in an office with a view. So I drove a half-hour into town to see for myself, uncertain what Wendell thought I would findso clarifying there. Riding the elevator up, my reflection rippled in the scratched, stainless steel doors in front of me, looking like a leaner, taller ghost of my father. On the top floor, I saw only three suite numbers: 1700, 1710, and 1720. I rang the bell at 1700, where a woman with graying blonde hair and sleepy eyes answered. I explained I was writing something about my relationship with my father and trying to hunt down his old office. Albeit bemused, she was nice enough to let me in and give me a quick tour. She explained that this suite connected to 1720 but there was no room #1727, not even 27 separate offices on that floor. The place had clearly been redesigned since my dad last stepped foot there. It was hard to believe that any rock concerts were ever planned in this now drowsy, overly air-conditioned space. But what I did see, everywhere I looked, were plate glass windows waist-high to ceiling. It was the kind ofspace where an overachiever could dream big while watching the world spin down below — exactly like something I would prefer, for I need a window nearby to write. 'I'm sorry I don't know any more,' the office worker said before walking away. I snorted a laugh and had to accept that I would never know my father like I wanted — that a history of objects can reveal but never resurrect — and also that, to some degree, he'd been there right in front of me. That private but friendly guy always working, always dreaming — that was my dad. A dozen years after my father's passing, the days of selling rock files are done. My mother eventually sold what was left in the file cabinet to a local collector who's creating an archive of the Birmingham music scene with the hopes of turning it into a museum. The archivist hauled away that clanky metal thing that, although lighter from fewer files, still had to be hand-trucked out by two strong one day, Dad's papers and accomplishments could be on public display. Mom kept a few favorites, including that black-and-white poster of Stevie Nicks and Lindsey Buckingham, forever frozen in their 20s, forever beautiful, boldly staring back at the viewer like wild-haired rock gods. Mom displayed it in her living room, a reminder of when she and Richard were young. Over the years of sellingrock documents, the parent I got to know was my mom. Even though she frequently griped about Dadnot being more involved in child care and housekeeping, I could tell part of her still loved him — the version of Richard before the disease of depression stole himfrom us. That's why she kept selling these rare items, not for the money, which she didn't need, but to keep his memory living and moving,just like the music they both craved. Remembering is also reacquainting. Although I thought I never played for my father again, that's not entirely true. I never played for him in person. While writing this essay, a memory returned to me: I used to keep in touch with Richard over the phone in the early days of his decline, when there was still some little spark of the old dad inside him. I must've been practicing guitar during a call one evening (a habit I still have) because he grew silent, listening to me play. I stopped plucking the strings, anxious. 'You sound good, son,' he finally said. 'Sound really good.' 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