BRAD PITT AND GWYNETH PALTROW
This it couple from the 90s dated between 1995 and 1997. Blonde, tall, beautiful, even at some point with the same hair (see picture above), they almost seemed too good to be true.
JOHNNY DEPP AND WINONA RYDER
They met in 1989, when Winona was only 17 and got engaged five months later. They were Hollywood's favorite dark couple, but ultimately, they ended up parting ways in 1993.
LENNY KRAVITZ AND NICOLE KIDMAN
Did you know these two were engaged in the early 2000s? Apparently, they were together in 2002-2003, and even thought of marriage, but weren't right for each other in the end.
RYAN REYNOLDS AND ALANIS MORISSETTE
Even if they seem like an odd pairing, the Ironic singer and the Deadpool star, were an item for five years, and engaged for two, before they broke up in 2007.
MICHAEL BUBLE AND EMILY BLUNT
The singer and the actress were together for five years, and they had an ugly split in 2008, surrounded by rumors of infidelity. In the end, they got married and had children with their respective partners, Luisana Lopilato and John Krasinski.
CAMERON DIAZ AND JARED LETO
Before marrying her singer husband Benji Madden, Díaz went out with the 30 seconds to Mars singer (and actor) Jared Leto, between 1999 and 2003, and they even got engaged.
JENNIFER LOPEZ AND BEN AFFLECK
These two superstars had a high profile romance with Hollywood ingredients: met on a movie set, expensive diamond ring, and calling off the wedding four days before the big celebration in 2004.
JULIA ROBERTS AND KIEFER SUTHERLAND
Another scandalous superstar couple that broke up just days before their wedding: they dated for a year until Roberts called it off in 1991, allegedly to be with Kiefer's friend, actor Jason Patric.
EVAN RACHEL WOOD AND MARILYN MANSON
This tumultuous relationship started when Wood was only 19, and Manson almost 40. They had an on and off relationship until he proposed in a concert in 2010. They broke up a few months after that.
LAURA DERN AND BILLY BOB THORTON
These two started dating in 1997 and he popped the question in 1998, only to run away after Angelina Jolie the year after, without notice or explanation to his fiance.
JUDE LAW AND SIENNA MILLER
These two met on the set of Alfie, in 2004, and got engaged that same year. Sadly, he cheated with his children's nanny, so the couple split up in 2006.
KATE MOSS AND PETE DOHERTY
The musician and the supermodel had a turbulent relationship fueled by their addiction to alcohol, drugs and partying. They started dating in 2005, got engaged, and parted ways for good in 2007.
ROSE MCGOWAN AND MARILYN MANSON
The eccentric rock singer and the Charmed actress were engaged from 1998 to 2001, when McGowan ended the relationship allegedly over his drug abuse, citing "lifestyle differences".
RACHEL WEISZ AND DARREN ARONOFSKY
The couple dated for 9 years and had a son together, but they broke their engagement in 2010, allegedly because she was already having an affair with co-star Daniel Craig, whom she ended up marrying.
LAURA DERN AND JEFF GOLDBLUM
The Big little lies actress and The fly actor met on the set of Jurassic Park and went on to get engaged in 1995. They ended up parting ways in 1997.
LADY GAGA AND TAYLOR KINNEY
The superstar singer and the actor were together for four years before he popped the question on Valentine's Day in 2015. The couple announced their break up in 2016.
CARSON DALY AND TARA REID
The TV host and the actress, dated in the early 2000s. They met on the Total Request Live set in 200 and got engaged soon after. They broke up in 2001.
JULIA ROBERTS AND DYLAN MCDERMOTT
They met in 1988 on the set of Steel Magnolias, where they played husband and wife. They got engaged, but she broke up with him soon after to date Kiefer Sutherland.
JENNIFER MORRISON AND JESSE SPENCER
The actors met on the set of the acclaimed drama House and started dating in 2004. After a very romantic proposal in the Eiffel tower in 2006, they broke up the following year.
BRITNEY SPEARS AND JASON TRAWICK
The pop star and the agent started dating in 2009, soon after he started representing her. They got engaged in 2011 but ended up calling off their wedding after two years.
MARK RONSON AND RASHIDA JONES
The actress and the DJ and record producer met in 2002 and broke up in 2004. They even got engaged at some point but called it quits that same year.
MARY-LOUISE PARKER AND JEFFREY DEAN MORGAN
The actors met on the set of the tv series Weed in 2006 and got engaged in 2008, after two years of on-again off-again relationship. They separated soon after.
DEMI MOORE AND EMILIO ESTEVEZ
Back in the 80s, Demi Moore and Emilio Estevez were an item: they met on the set of Wisdom in 1984, got engaged a year later, and ended up breaking up in 1987.
MICHAEL BOLTON AND NICOLLETTE SHERIDAN
This couple had a long-lasting love story: they dated for five years in the 90s, broke up, and then in 2005 they reconnected, got engaged, but ended up breaking up for good in 2008.
KATIE HOLMES AND CHRIS KLEIN
These actors started dating in the late 90s and ended up getting engaged in 2003, after five years of a steamy romance. Sadly, they broke up two years later.
HEATHER LOCKLEAR AND JACK WAGNER
The Melrose Place co-stars began dating in 2007, and got engaged in 2011. Ultimately, the pressure of organizing the wedding ended up being too much and they broke up 3 months after.
SHERYL CROW AND LANCE ARMSTRONG
The Grammy award-winning singer and the now-disgraced cyclist surprised everyone when they started dating in 2003 and got engaged in 2006, only to break up five months later.
BEN STILLER AND JEANNE TRIPPLEHORN
Before getting married to Christine Taylor, actor and director Ben Stiller was engaged to actress Jeanne Tripplehorn. They started dating in 1990 and were engaged for three years until they separated in 1995.
SANDRA BULLOCK AND TATE DONOVAN
The Oscar-winning actress and the actor met in 1992 on the set of Love Potion No. 9 and dated for three years, before parting ways in 1995.
CARRIE FISHER AND DAN AYKROYD
The actors met on the set of the 80s classic The blues brothers, and he proposed to her on set. In 1983, Fisher reconciled with her ex Paul Simon and ended up marrying him instead.
SIMON COWELL AND MEZHGAN HUSSAINY
TV host and mogul Simon Cowell and Hussainy were in a long-term relationship of 7 years, before getting engaged in 2010. Things didn't work out and they parted ways in 2011.
DREW BARRYMORE AND LELAND HAYWARD
The actress was only 16 when she started dating Hayward, grandson of Hollywood producer Leland Hayward and got engaged soon after. Thankfully, the engagement was called off a few months later.
DREW BARRYMORE AND JAMIE WALTERS
After breaking up their engagement with Hayward, a teenager Barrymore started dating the actor and musician Jamie Walters. They got engaged but ended up calling it off a few months later, in 1993.
BIG SEAN AND NAYA RIVERA
The Glee actress and the rapper met on Twitter and started dating in 2013. In October of that same year they got engaged, but the rapper called it off in 2014.
ROSAMUND PIKE AND JOE WRIGHT
The Gone girl actress and the Atonement director met on the set of Pride and Prejudice, in 2005. He proposed in 2007, but they ended their relationship a year after.
ZOE SALDANA AND KEITH BRITTON
The actress and the entrepreneur had a long-term relationship. They started dating in 2000 and announced their engagement in 2010, only to break up in 2011.
PARIS HILTON AND PARIS LATSIS
The Paris started dating in 2004 and got engaged in 2005. Despite having the same name and being heirs and billionaires, their relationship didn't work out and they broke up in 2005.
DANIEL CRAIG AND SATSUKI MITCHELL
The actor and the film producer dated for over ten years and were engaged for four, but in 2011 Craig fall for co star Rachel Weisz, and the engagement was off.
GINNIFER GOODWIN AND JOEY KERN
The Cabin Fever actor and the Once Upon a Time actress got engaged in December 2010, but they broke things off only a few months later, in May 2011.
JOSH BROLIN AND MINNIE DRIVER
The actors met in the set of their movie Slow Burn in 1998 and got engaged soon after. In October 2011, Driver called off their 3-year engagement.
MARIAH CAREY AND JAMES PACKER
The singer and superstar met Australian billionaire in 2014 and got engaged in January 2016, but broke up in October of the same year, after a tumultuous vacation in Greece.
JAY BARUCHEL AND ALISON PILL
The Canadian actors got engaged in 2011, but Pill called if off in March 2013. Baruchel alluded to the break up in a Twitter post that said "Getting dumped rules".
KERRY WASHINGTON AND DAVID MOSCOW
The actors started dating in 2003 and in 2004 they got engaged. In 2007, when she turned 30, she broke off the engagement to focus on herself and her career.
KALEY CUOCO AND JOSH REZNIK
The Big Bang Theory star and the addiction specialist got engaged in October 2011, but the love didn't last, and they broke up a year later.
ROSE MCGOWAN AND ROBERT RODRIGUEZ
The actress and the director met in Cannes, in 2005, and they began their relationship when he cast her in his movie Grindhouse. They eventually got engaged in 2007 and split up in 2009.
NICK CANNON AND SELITA EBANKS
The comedian and Victoria's secret model began dating in 2007 and he proposed to her in May of that same year in Times Square. Five months later, they broke up.
KANYE WEST AND ALEXIS PHIFER
Before dating Kim Kardashian, rapper Kanye West was engaged to designer Alexis Phifer, and they even got engaged after going out for 4 years. They announced their separation 2 years later.
ROBIN WRIGHT AND BEN FOSTER
The House of cards star began dating actor Ben Foster in 2012 and they announced their engagement in January 2014 but ended up parting ways for good in August 2015.
RUBY ROSE AND PHOEBE DAHL
The Orange is the new black actress and the fashion designer announced their engagement in 2014. But, a year and a half later, they called off their wedding.
ZAYN MALIK AND PERRIE EDWARDS
The pop singers began dating in 2011 and Malik popped the question two years later but broke it off in 2015. Edwards then claimed he dumped her via text message.
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