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15 Celebrity Couples That Most People Probably Forgot Were Engaged

There's nothing that Hollywood loves more than a wedding. Over the years, some of our favorite stars have come dangerously close to walking down the aisle with partners that may surprise you.

To give you a better idea, here are 10+ celebrity couples that you probably forgot were once engaged. Have a look and try to imagine how much different their loves might have looked had they wound up saying "I do."

Drew Barrymore and Leland Hayward

Drew Barrymore's teen years were tumultuous at best.

She legally emancipated herself at 14, moved into her own apartment by 15, and then a year later she was engaged to fellow actor, Leland Hayward III.

Tate Donovan and Jennifer Aniston


A few short months after calling off their engagement, Tate was cast to play Joshua on Friends. That's right — Rachel and Joshua were actually engaged in real life

According to Tate, the whole ordeal was absolute torture.

Kiefer Sutherland and Julia Roberts

Kiefer and Julia met on the set of the 1990 psychological thriller, Flatliners. At the time, Kiefer was in the midst of a nasty divorce from former flame Camelia Kath.

Sadly, less than a year after moving in together and announcing their planned nuptials, Kiefer and Julia decided to call it quits.

Alanis Morissette and Ryan Reynolds

Don't get me wrong, I'm incredibly happy that Ryan and Alanis have found their forever people. But these two were the living embodiment of a Canadian power couple.

I genuinely was hoping they'd find a way to make it work, at the time.

Kerry Washington and David Moscow

The name David Moscow might not ring any bells, but I bet you'd recognize him from his role as Young Josh in Big.

These two were engaged for three whole years before finally deciding to call it off in 2007.

Demi Moore and Emilio Estevez

I'm a '90s kid, who just missed the boat on the Brat Pack. But as far as I'm concerned, St. Elmo's Fire ranks in the highest echelon of '80s films.

Unfortunately for Demi and Emilio, their spark wasn't able to catch flame.

Jeffrey Dean Morgan and Mary-Louise Parker

I had completely forgotten that JDM starred in Weeds, let alone that he was at one time engaged to Mary-Louise Parker.

The couple announced their plans to wed in February of 2008 and had split by April of that same year.

Sandra Bullock and Tate Donovan

My goodness, Tate Donovan really gets around! Not so ironically, he and Sandra met and fell in love on the set of Love Potion No. 9.

They were engaged for three years but never made their way down the aisle.

Sienna Miller and Jude Law

I still remember a time when Jude Law and Sienna Miller were considered by many to be the most beautiful couple on the entire planet.

But after rumors about Law's affair with the couple's nanny were confirmed, Sienna said her goodbyes to the one-time sex symbol.

Johnny Depp and Winona Ryder

After Johnny and Winona met filming Edward Scissorhands, they began a torrid love affair.

Depp says that the reason for the demise of their relationship was due to intense pressure brought on by the media.

Sheryl Crow and Lance Armstrong

Sheryl started dating Lance in 2003; the same year that he got divorced from his wife.

Try as they did, Sheryl and Lance just couldn't find their harmony and less than a year later decided to go their separate ways.

Alyssa Milano and Scott Wolf

Talk about a throwback from way back! Does anyone else remember the movie Double Dragon or was I literally the only person who watched this movie as a kid?

Anyway, these two started dating two months after filming and were engaged after four. But by the very next year, they were no more.

Brad Pitt and Gwyneth Paltrow

The idea of Brad and Gwyneth just seems foreign to me. Try as I might, I could just never picture these two together.

Gwyneth clearly felt the same and decided to call off the engagement, on the grounds that the relationship had become toxic.

Jennifer Lopez and Ben Affleck

I recall when Bennifer was on every single cover of every single magazine in print; what a time to be alive.

But after being dragged through the mud in the media and co-starring in arguably the worst movie ever made, these two went their separate ways...at least until recently.

Sean Penn and Charlize Theron

Charlize and Sean dated for a little more than a year and rumors say that they were headed down the aisle after getting secretly engaged.

However, it should also be noted that Charlize vehemently denies these claims. Almost a little too vehemently.