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6 Celebrity Engagements That Came To A Crashing Halt

6 Celebrity Engagements That Came To A Crashing Halt

Tinseltown twinkles with fairytales on screen, but off-camera, love stories often flicker out like dying bulbs. We’ve witnessed the dazzling diamond announcements, the magazine spreads overflowing with bliss, only to be left scratching our heads when whispers of “uncoupled” echo down the red carpet. In this list, we peel back the curtain on seven Hollywood engagements that went from “I do!” to “Never mind…” Broken promises, shattered champagne flutes, and the quiet fizzling of celebrity romance abound as we unveil the truth behind love’s demise under the harsh glare of the spotlight.

Kiefer Sutherland E Julia Roberts, Smile, Hairstyle, Facial expression, Human, Coat, Bow tie, Gesture, Happy

Julia Roberts and Kiefer Sutherland

Back in 1991, Kiefer Sutherland and Julia Roberts, who were among Hollywood’s hottest young stars at the time, had a relationship that appeared destined for a true “happily ever after” fairy tale ending. So when Roberts broke up with him three days before they were to profess their eternal love for each other, it was quite a shock. To add insult to injury, she dumped Sutherland for his BFF Jason Patric!

Gentleman, Hairstyle, Smile, Product, Vision care, Fashion, Flash photography

Carson Daly and Tara Reid

Celebrity couples often rush through their marriages, but it appeared that Carson and Tara were taking a smart, slow, deliberate approach. Just kidding. After Daily ended a lengthy bicoastal relationship with Jennifer Love Hewett, he and Reid jumped right into things and announced that they were planning to get married after a mere 7 months of dating. But as quick as their relationship had started, it was over. Reid, who has been engaged multiple times but has never tied the knot, stated years later that she regrets that they didn’t get married, as she’d likely have been a mother and curbed her crazy partying lifestyle.

Emilio Estevez Sonja Magdevski Split, Flash photography, Tie, Smile

Demi Moore and Emilio Estevez

Demi Moore and Emilio Estevez, fresh off of their success as co-stars in St. Elmo’s Fire, announced a December 13, 1986 wedding date. They had even gone so far as to send out invitations. But shortly before the ceremony was supposed to take place, they put out an announcement that they intended to just stay friends. Moore married Bruce Willis the following year. There didn’t appear to be any hard feelings, though. When Estevez directed Bobby in 2006, a film that featured Demi and her second husband Ashton Kutcher, he spoke glowingly about being able to work with her again. 

Lance Armstrong Sheryl Crow, Watch, Hand, Hairstyle, Vertebrate, Mammal, Gesture

Lance Armstrong and Sheryl Crow

Soon after Lance filed for divorce from his first wife in 2003, he began dating the legendary singer. After celebrating their 2-year anniversary as a couple, they announced their engagement. However, a few short months later, they parted ways. As the cyclist would explain in his 2009 biography, Crow wanted children whereas he had just had 3, and she wanted to get married when he had just gotten out of one. 

Gwyneth Paltrow And Brad Pitt, Hair, Glasses, Smile, Vision care, Shoulder, Goggles, Sunglasses, Eyewear, Happy

Gwyneth Paltrow and Brad Pitt

These Hollywood A-listers first met in 1995 on the set of Seven, and soon romance was in the air. When they got engaged, they marked the occasion with a huge party at Paltrow’s parents house. Their wedding date was set for the summer of 1997 but, alas, it wasn’t meant to be. Pitt had expressed excitement about the prospect of marriage in an interview with Rolling Stone, but at 25 years old, Gwyneth decided she was not yet ready to settle down. 

Jennifer Lopez Wed Ben, Smile, Hairstyle, Facial expression, Comfort, Gesture

Jennifer Lopez and Ben Affleck

Bennifer pretty much birthed this whole “let’s refer to celebrity couples as a single entity that blends both of their names” trend that remains to this day. When the Ben side of the duo forked over $1.2 million on a 6.1-carat pink diamond engagement ring, their marriage felt like a done deal. However, they postponed the wedding a few days before they were set to walk down the aisle. The good news: nearly 20 years and a pair of divorces later (he to Jennifer Garner and she to Marc Antony), they finally did tie the knot on July 16, 2022.

Tags: Julia Roberts