Entertainment
With the rate that the tabloids throw celebrity break-ups and make-ups at you, it can be hard to keep track of who's with who in the grand scheme of celebrity love entanglements. Even more shocking is all the celebrities you forgot were engaged to one another at some point in time. While jogging my memory to compile this list, I got a rude awakening of just how many celebrity power couples got engaged in the '90s and never actually made it. But I'd be lying if I said it's not fun to reminisce on all the couples that used to be.
Of course, most (if not all) of these celebs have moved on from their broken engagements of yesteryear and found love again. Some of them have even found love multiple times, sifting through engagements and marriages and taking their turn in the celebrity spotlight for something completely normal: trying to make a relationship work. Although these celebrity couples of the past didn't make it all the way, it's way too fun to picture them as a couple now than to forget that they were ever engaged. So read on for a good dose of celebrity nostalgia, and remember all the celebrity couples that used to be.
1
Cameron Diaz and Jared Leto
According to IMDB, Cameron Diaz and Jared Leto dated for four years dated and were allegedly engaged towards the end, when Diaz started sporting an engagement ring. Diaz dated a string of successful men before settling down with her current husband, Benji Madden.
2
Alanis Morisette and Ryan Reynolds
In 2004, People reported that Alanis Morisette and Ryan Reynolds got engaged and became Canada's power couple. Though the engagement lasted for three years, the two never made it to the altar. The pair split in 2007, and Morisette channeled their breakup on her 2008 album Flavors of Entanglement.
3
Tara Reid and Carson Daly
Tara Reid and Carson Daly got engaged back in 2000, when MTV was in its heyday, but went their separate ways in 2001. In an interview with Elle in 2012, Daly described breaking off their engagement as though he "dodged a bullet." Reid on the other hand was pretty broken up about it.
4
Alison Pill and Jay Baruchel
Another cute Canadian couple that had to call it quits, Alison Pill and Jay Baruchel were engaged for two years before calling it off in 2013. According to Us Weekly, Baruchel took to Twitter to lament his heartbreak.
5
Kate Moss & Pete Doherty
Kate Moss and Pete Doherty had a long and tumultuous are-they-aren't-they relationship that rumors practically chased after. Though some reports stated that the two weren't actually engaged, during a performance in 2007, Doherty referred to Moss as his fiancée.
6
Nicolette Sheridan and Michael Bolton
Nicolette Sheridan and Michael Bolton's first relationship began in 1992 and lasted for five years. Since it didn't work out the first time around, the two tried again, getting back together in 2005, and announcing their engagement in 2006. People reported in 2008 that the couple was going their separate ways.
7
Laura Dern and Billy Bob Thornton
Laura Dern and Billy Bob Thornton were engaged to be married, and ABC News reported that Dern opened up about the breakup in Talk magazine. “I left our home to work on a movie, and while I was away, my boyfriend got married, and I’ve never heard from him again.” Dern went on to say that there's never been any closure or clarity on the matter. Yikes.
8
Evan Rachel Wood and Marilyn Manson
Evan Rachel Wood and Marilyn Manson began their relationship in 2006, when she was just 19, and he 36. Though their relationship and engagement was the subject of much controversy, Wood doesn't regret it. "I wouldn’t trade any of [our relationship]," Wood said in an interview with The Edit. "I appreciate everything he taught me. I just don’t think we were right for each other."
9
Sheryl Crow & Lance Armstrong
Sheryl Crow and Lance Armstrong were a couple from 2003 to 2006, and were engaged for a brief period of time before they split. Crow opened up to The Telegraph about their relationship, noting that Armstrong's doping controversy wasn't the reason they split.
10
Gwyneth Paltrow and Brad Pitt
According to Us Weekly, Brad Pitt proposed to Gwyneth Paltrow in 1996, and less than a year later in 1997, they called it off.
11
Demi Moore & Emilio Estevez
Before Demi Moore married Bruce Willis and had a gaggle of children, Moore was engaged to Emilio Estevez. They were to be married in 1986, but called off the engagement. The two were reunited at the premiere for their film Bobby in 2006.
12
Courteney Cox and Michael Keaton
Though Courteney Cox and Michael Keaton were together for over five years, they called off their engagement in 1995, according to People. "It's the most important relationship I've ever had, and I think he's the most wonderful person I've ever met," Cox told the magazine. Recently, rumors were stirred up that the couple was reuniting their flame, but the rumors were quickly squashed.
13
Julia Roberts and Kiefer Sutherland
Julia Roberts and Kiefer Sutherland were engaged from 1990 to 1991. People reported that just days before their wedding, she broke off the engagement and fled their wedding plans with Sutherland's best friend, Jason Patric.
14
Katie Holmes & Chris Klein
The poster kids for all-American '90s romance, Katie Holmes and Christ Klein dated for five years and were engaged for two. They called off their engagement in 2005, and Klein opened up to The Daily Beast about their split, stating that things didn't work out because they were young, and still growing up.
15
Winona Ryder and Johnny Depp
According to People, Winona Ryder and Johnny Depp got engaged when she was just a teenager. The pair met on the set of Edward Scissorhands, and split three years later when she was just 19.
