Julia Roberts and Kiefer Sutherland met on the set of their movie “Flatliners” in 1990, right when Sutherland was finalizing a divorce. The two began dating soon after and were living together by the end of that same year. Rumors started going around about Sutherland being unfaithful, but they were all silenced when the couple announced they were engaged and scheduled for a big celebrity wedding in June of 1991.
But just three days before their scheduled wedding, Roberts called off the engagement. Roberts eventually married cinematographer Daniel Moder in 2002 and went on to have three children. Sutherland’s love life was slightly rockier – he got married and divorced and has had a slew of relationships in between until finally settling down with partner Cindy Vela, also an actress.
Demi Moore and Emilio Estevez
The 1985 coming-of-age hit film “St. Elmo’s Fire” brought co-stars Demi Moore and Emilio Estevez together. They started dating for some months and were engaged by the end of that same year. For the next two years, Moore and Estevez broke up and got back together several times, until finally setting a wedding date for December of 1986.
Not surprisingly, they finally called it off for good a few months later. Moore married actor Bruce Willis in 1987, with whom she had three gorgeous daughters. Even though they divorced in 2000, they remain very close. Moore married Ashton Kutcher in 2005 and then divorced him in 2013. Since then, the beautiful actress has been enjoying the single life with her cute dog Pilaf.
Jason Wahler and Katja Decker Sadowski
“The Hills” and “Laguna Beach: The Real Orange County” actor Jason Wahler is now happily married to model Ashley Slack. However, back in 2007, he almost pledged his undying love to somebody else – Katja Decker Sadowski. They started dating in February of 2007, and by August of that same year, they were engaged.
The engagement bliss lasted until February 2009, when Wahler decided to call off the wedding. The actor said they had broken up amicably and simply decided that “they were both just too young to be considering getting married right now.” Well, it’s definitely better to admit that before any forever commitments are made.
Ruby Rose and Phoebe Dahl
Actress and “Orange Is the New Black” star Ruby Rose met Phoebe Dahl in 2014, at a barbecue of a mutual friend. Dahl, granddaughter and heiress to famous English writer Roald Dahl, immediately fell for the wild and gorgeous Ruby. And apparently, the feeling was mutual.
The two started dating, and after just three months, they got engaged. However, the engagement lasted little over a year, as they announced they were going their separate ways by the end of 2015. As Dahl explained to the press, "Our break is not the result of any media speculation, and we want nothing but the best for each other."
Sean Penn and Charlize Theron
Sean Penn definitely has good taste in women. After splitting up with his actress Robin Wright, Sean Penn fell for none other than South African beauty Charlize Theron. These two Hollywood A-listers got together in 2013 and got engaged a short year later; but alas, it wasn't meant to be. After 18 months of dating, they decided to go their separate ways.
The tabloids had a field day with their breakup, but thankfully, Theron cleared everything up. Like the classy lady that she is, the “Mad Max: Fury Road” star cleared the air, saying that sometimes relationships just don't work out, and in this case, they both decided to separate amicably. Oh well, as long as it was amicable.