Celebrity Couples You Forgot Were Engaged

With all the celebrity couples getting engaged and un-engaged these days, we thought it would be a great time to take a trip down memory lane and reflect on all of the other couples who coupled and uncoupled (consciously or not) over the years.

I bet you forgot that some of these famous pairs even dated at all. Keep reading to learn about the it-couples of yesteryear.

Emilio Estevez and Demi Moore

Emilio Estevez and Demi Moore met on the set of St. Elmo’s Fire. They started a romantic relationship and even got engaged. In 1987, they broke off their engagement. Shortly after that, Demi Moore started dating her future husband, Bruce Willis.

Then they got divorced and she married Ashton Kutcher, and then they got divorced.

Kiefer Sutherland and Julia Roberts

Kiefer Sutherland and Julia Roberts were engaged in the early 1990s, but Julia called off the wedding just a few days before it was supposed to take place. Maybe she should have starred in Runaway Bride.

Oh wait, she did. Well, that makes sense.

Amber Rose and Kanye West

Before Kaye married Kim Kardashian, he was engaged to Amber Rose. Actually, before he was engaged to Amber Rose, he was engaged to designer Alexis Phifer.

Sadly, Kim and Kanye’s marriage didn’t last too long.

Kate Moss and Pete Doherty

Model Kate Moss and the Libertines frontman Pete Doherty were briefly engaged in 2007. After his engagement to Moss, Doherty was briefly engaged to model Irina Lăzăreanu.

Doherty definitely has a thing for models. Unfortunately, he couldn’t make any of those relationships stick.

Alanis Morisette and Ryan Reynolds

You oughta know that Alanis Morisette and Ryan Reynolds were an item from 2002 to 2007. They were even engaged, but they called off their engagement before they ever got married.

It’s hard to imagine Ryan Reynolds with anyone other than Blake Lively. Alanis has also found a husband, so everybody is doing just fine.

Heather Locklear and Jack Wagner

Jack Wagner and Heather Locklear met on the set of Melrose Place. They didn’t start dating until years after the show ended, though. They began a relationship in 2007, right after Locklear’s second divorce was finalized.

They got engaged in August of 2011, but called off the engagement just a few months later.

Carson Daly and Tara Reid

Carson Daly and Tara Ried together are what ’90s dreams are made of. Just saying their names take me back to the days of Slinkies and Sony Walkmen.

Carson proposed to Tara in October of 2000, but by the summer of 2001, they had called off the wedding.

Billy Bob Thornton and Laura Dern

Billy Bob Thornton and Laura Dern were engaged in 2000. Billy Bob has actually been married six times and divorced five, so luckily this relationship ended before they made things legal. Seven marriages would just be too much.

Thornton married Angelina Jolie shortly after breaking up with Laura Dern.

Jude Law and Sienna Miller

Sienna Miller and Jude Law almost got married in the mid 2000s, but they called the whole thing off after Sienna discovered that Jude was having an affair with his children’s nanny.

Even though they called off the wedding, they still continued to date until 2011.

Courteney Cox and Michael Keaton

Courteney Cox and Michael Keaton were together from 1989 – 1995. Their relationship predates Friends and lasted until the first season of the show started airing. At the time, neither Courteney nor Michael knew how big the show was going to be.

They didn’t end up getting married, but they were engaged for a while.

Katie Holmes and Chris Klein

American Pie actor Chris Klein was engaged to Katie Holmes in 2003. The couple called off their engagement and ended their relationship in 2005. Klein went on to marry a travel agent named Laina Rose Thyfault. They have two children together.

Katie Holmes went on to marry Tom Cruise, and we all know how that went.

Sheryl Crow and Lance Armstrong

These two began their romantic relationship back in 2003. They got engaged in 2005, but called off their engagement in 2006.

At the time, Lance was freshly divorced from his first wife, and Sheryl was about to discover that she, like Lance, would also have to face a battle with cancer.

Rachel Weisz and Darren Aronofsky

These two lovebirds were engaged from 2005 to 2009. Unfortunately, it wasn’t meant to last. Rachel would go on to marry Daniel Craig.

Nicollette Sheridan and Michael Bolton

Nicollette Sheridan must have fallen for Michael Bolton’s sultry voice, because these two were engaged for two years before they broke up in 2008.

This was actually the second time that Michael and Nicollette broke up. They dated for five years back in the ’90s.

Winona Ryder and Johnny Depp

We all remember that Winona and Johnny were an item. They were the most iconic couple of the ’90s. In fact, I kind of wish that they were still a thing. But did you remember that they were actually engaged from 1990 to 1993?

I kind of wish that we got to see that Burton-esque wedding.

Nicole Richie and DJ AM

Nicole Richie and DJ AM (or DJ Adam Michael Goldstein) began dating in 2003. Her influence and star power caused his career to skyrocket. Unfortunately, this relationship just wasn’t meant to be.

Richie and Goldstein called it quits, and a few years later, Goldstein died of a drug overdose.

Gwyneth Paltrow and Brad Pitt

Gwyneth Paltrow and Brad Bitt dated from 1994 to 1997. They were even engaged for a bit. Gwyneth would go on to marry and later divorce Coldplay frontman, Chris Martin. She recently married producer Brad Falchuck.

Ed Norton and Courtney Love

Courtney Love and Edward Norton actually dated for four years, and they were even engaged at one point.

Love said, “I should have married Edward. I left him for a bad man who stole all my money.” I guess you live and you learn. We all should have married Ed Norton.