"Bennifer" only dated for four months before becoming engaged in November 2002. There was huge media buzz surrounding the wedding, but four days before it was set to take place in 2003, the couple called it off.
After dating for two-and-a-half years, the couple became engaged, but split six months later. "We were up against her biological clock — that pressure is what cracked it," the cyclist later said. Sheryl went on to adopt two sons as a single mom.
After meeting on the set of Seven, the pair dated for nearly three years (with a six-month engagement) before calling it quits in 1997. Gwyneth later said she couldn't believe Brad went out with her, given she was "such a mess."
The young actors were supposed to marry on Dec. 13, 1986, but called off the ceremony shortly before, announcing their decision to remain "just friends." Demi tied the knot with Bruce Willis the following year.
The A-list couple were set to tie the knot at 20th Century Fox's Soundstage 14 in 1991, but three days before the ceremony, Julia ran off with the actor's best friend. More than a decade later, Kiefer admitted, "I commend Julia for seeing how young and silly we were, even as painful and difficult as it was."
The Canadian duo got engaged in 2004 and shocked fans by separating three years later. "They remain close friends and continue to have the utmost love and admiration for each other," their reps said at the time.