19 Celebrity Couples Who Broke Off Their Engagements

Two years into their relationship, Reynolds proposed in 2004. Their engagement was a long one — four years — before they realized they weren't each other's end game.

RELATED: 32 Celebrity Couples Who Called it Quits Recently

Before Angie, there was Jen. But before Jen, there was Gwyneth, the original golden couple. They top the list of '90s couples who need to get back together. They dated for nearly two years but broke up in 1997.

They became engaged five months after their first date, when he was 27 and she was 18. He got his infamous "Winona Forever" tattoo but, alas, things don't always last that long and by 1993, their engagement was off and "Wino Forever" lives on.

They met on the set of Gaga's video for "You and I" back in 2011 and started dating almost immediately. Kinney popped the question on Valentine's Day in 2015 with a heard-shaped diamond, and it was one of 24 celebrity engagements rings we adored! But just over a year later, the two announced they were done.

The billionaire proposed with a 35-carat diamond and naturally Mimi said yes. But less than a year later, there were reports the two were on a break. Those reports led to both sides revealing they were over for good, with Mariah focused on her reality show and James wanting nothing to do with it.

These two got engaged in 2004 but it was seven months later that she — and we — learned about Law's affair with his kids' nanny. Naturally, they called it quits but the two briefly reunited in 2010, making them just one Hollywood couple who survived cheating and stayed together. They parted ways for good shortly after, though.

Nick and Selita met at a Super Bowl party in 2007, he proposed three months later, and they were done five months after that. Yep, about right.

Demi and Emilio were '80s fire after meeting on the set of St. Elmo's Fire. Their engagement, however, was brief and the duo were done almost as quick as they began.

Their on-off relationship should've been a sign; after seven short engaged months, they called it and were permanently off. It's probably also due to the fact that they first got together while Manson was with Dita Von Teese. To this day it remains one of the most scandalous celebrity love triangles of all time.

When a guy writes a song about you, it can be cheese. But "Everything" was anything but. They got engaged in 2005 but split three years later. We're totally OK with this since Blunt and John Krasinski are perfection together.

They dated for six short months before deciding they were each other's lobsters. Um, nope. The couple broke up two months before their July 2014 wedding.

She left Dylan McDermott for Kiefer, and the two were engaged. It seemed to be going swimmingly until she called off the wedding three days before it was supposed to go down and took off with her and Sutherland's friend, Jason Patric. Damn.

Aw, how cute were these two? They began dating in 2000, engaged three years later and two years after that, they split.

They met in 2000, when she was one of the stars of American Pie and appeared on his show, Total Request Live. They were engaged by October of that year but they were broken up by the following summer.

Their nine-year relationship — five of which they spent engaged — ended in 2010. But they have a beautiful son together.

The NBA star and rapper celebrated their engagement in June 2015 but she broke up with him the following year, and accused him of cheating.

The tattoo artist and DJ got engaged two months after dating, in December 2012. They had big plans for an underwater-themed wedding but they called it quits in June of the following year.

They were engaged in 2005, after two years of dating, but announced their split the following year.

The two met on the 2002 set of Gigli and were engaged that same year. Ben popped the question with a pink diamond but it all became too much and just like their first movie, these two crashed and burned in 2004, in one of the most scandalous breakups in modern Hollywood history.