Celebrities and Their Almost "I Do’s"

Celebrities who met in a film and shared the same passion that ended up in the “will you marry me” phase is already a common thing. However, some people just aren't meant to be. Here are 25 former star couples who made it to "Will you marry me" and "Yes and I will" but weren't able to share their "I do’s".

Image Source: Getty Images/Ryan and Alanis

Image Source: Getty Images/Ryan and Alanis


25. ARIANA GRANDE ALMOST GOT MARRIED TO PETE DAVIDSON

The Focus singer Ariana Grande and the comedian Pete Davidson were first publicly seen together in 2016 and it was in the show "Saturday Night Live". The two started dating in May 2018 sometime after their break up confirmation with their respective partners. The same year they also got engaged with a diamond ring from Davidson and even had couple tattoos!

Image Source: Getty Images/Nicholas Hunt | Pete Davison and Ariana Grande attend the 2018 MTV Video Music Awards at Radio City Music Hall on August 20, 2018 in New York City

Image Source: Getty Images/Nicholas Hunt | Pete Davison and Ariana Grande attend the 2018 MTV Video Music Awards at Radio City Music Hall on August 20, 2018 in New York City

However, they had enough of their ups and downs so they eventually broke up.  It was then the birth of Grande's song, "Thank U, Next". Now Grande is in a relationship with Dalton Gomez and Davidson is single after his break up with Kaia Gerber last January.

Image Source: Getty Images/Raymond Hall | Singer Ariana Grande (R) and Pete Davidson are seen walking in Midtown on July 11, 2018 in New York City

Image Source: Getty Images/Raymond Hall | Singer Ariana Grande (R) and Pete Davidson are seen walking in Midtown on July 11, 2018 in New York City


24. MARILYN MANSON AND ROSE MCGOWAN SHARED A GREAT LOVE

After publicly showing their affection to each other, shock rock star Marilyn Manson and Rose McGowan called off their engagement in 2001. In an interview with Andy Cohen, McGowan said that in their relationship, there was great love but their difference when it comes to lifestyle is even greater.

Image Source: Getty Images/Steve Granitz | Rose McGowan & Marilyn Manson during "The Straight Story" Los Angeles Premiere at El Captain Theatre in Hollywood, California, United States.

Image Source: Getty Images/Steve Granitz | Rose McGowan & Marilyn Manson during "The Straight Story" Los Angeles Premiere at El Captain Theatre in Hollywood, California, United States.

Now, McGowan is in a relationship with a girl named Sienna. But before that, she had a relationship with Rain Dove. As of Manson, he is single at age 51 and his last relationship was with Lindsay Usich, which ended in 2015.

Image Source: Getty Images/Steve Granitz | Marilyn Manson & Rose McGowan

Image Source: Getty Images/Steve Granitz | Marilyn Manson & Rose McGowan


23. JOHNNY DEPP AND SHERILYN FENN PARTED WAYS FOR GOOD

It was in 1985 that the Hollywood actor Johnny Depp and actress Sherilyn Fenn during the set of the film Dummies. They were set to tie the knot as he even wrote her name in his helmet in the film Platoon. But sadly, they broke up and called off their engagement after being in a relationship for three and a half years.

Image Source: Getty Images/Donaldson Collection | Actress Sherilyn Fenn poses for a portrait in circa 1992 in Los Angeles, California

Image Source: Getty Images/Donaldson Collection | Actress Sherilyn Fenn poses for a portrait in circa 1992 in Los Angeles, California

Later on, Pirates of the Caribbean actor Johnny Depp had several marriages and engagements (more of that later) alongside his active acting career. On the other hand, Sherilyn Fenn is living with his son, Myles. She was previously married to Toulouse Holliday but is currently single who enjoys taking care of her cats and practicing yoga.

Image Source: Getty Images/Photo of Johnny Depp

Image Source: Getty Images/Photo of Johnny Depp


22. KYLE MACLACHLAN AND LINDA EVANGELISTA FIRST MET WHEN SHE WAS ALREADY MARRIED

As the supermodel Linda Evangelista prepared for a photoshoot, she met Kyle MacLachlan who joined the same photoshoot in 1992. They didn't share the love in the first story because that time, the supermodel was married to Gérald Marie but ended in divorce.

Image Source: Getty Images/Rose Hartman | Model Linda Evangelista and actor Kyle MacLachlan during 13th Annual CFDA Awards at the Lincoln Center in New York City, New York, United States, 7th February 1994

Image Source: Getty Images/Rose Hartman | Model Linda Evangelista and actor Kyle MacLachlan during 13th Annual CFDA Awards at the Lincoln Center in New York City, New York, United States, 7th February 1994

Eventually, MacLachland and Evangelista started dating and appeared on parties and events together. They were engaged for four years but it was called off. The Inside Out voice actor is happily married to Project Runway producer Desiree Gruber and they have a 9-year-old son named Callum.

Image Source: Getty Images/Richard Blanshard | American actor Kyle MacLachlan and his girlfriend, Canadian model Linda Evangelista attend a party for the film 'Ed Wood' at the Cannes Film Festival, France, May 1995

Image Source: Getty Images/Richard Blanshard | American actor Kyle MacLachlan and his girlfriend, Canadian model Linda Evangelista attend a party for the film 'Ed Wood' at the Cannes Film Festival, France, May 1995


21. DREW BARRYMORE AND LELAND HAYWARD GOT ENGAGED WHEN SHE WAS ONLY IN HER SWEET 16

Started as a child actress from a family of actors, Drew Barrymore experienced fading out of stardom but eventually had her comeback. She got engaged at the age of 16 to a man from a prominent Holywood family, Leland Hayward in 1991 but in the same year, they broke up.

Image Source: Getty Images/Ron Galella, Ltd./Actress Drew Barrymore and date Leland Hayward attend the "Sleeping with the Enemy" Westwood Premiere on February 4, 1991 at Mann Village Theatre in Westwood, California

Image Source: Getty Images/Ron Galella, Ltd./Actress Drew Barrymore and date Leland Hayward attend the "Sleeping with the Enemy" Westwood Premiere on February 4, 1991 at Mann Village Theatre in Westwood, California

Just recently, Barrymore was spotted hanging out at The Central Park with her ex-husband Will Kopelman and their second daughter Frankie. Their first daughter Olive wasn't able to join them. On the other hand, Hayward had several marriages and kids before he died in 1971 at age 68.

Image Source: Getty Images/Photo of Drew Barrymore

Image Source: Getty Images/Photo of Drew Barrymore


20. SANDRA BULLOCK AND TATE DONOVAN WERE IMMUNE TO THE LOVE POTION

Before Sandra Bullock and her now-boyfriend, Bryan Randall got all these “you two should get married” teasing from their friends, she was formerly engaged to Tate Donovan. Bullock and Donovan dated after meeting in the film Love Potion No. 9. They got engaged in the middle of their relationship but broke up in 1994.

Image Source: Getty Images/Vinnie Zuffante |  Sandra Bullock and Tate Donovan in LA 1994

Image Source: Getty Images/Vinnie Zuffante | Sandra Bullock and Tate Donovan in LA 1994


19. PERRIE EDWARDS IS A PART OF ZAYN MALIK’S HISTORY

The former member of One Direction, Zayn Malik dated and got engaged to Little Mix darling Perrie Edwards. The two seemed inseparable since they both love music but in 2015, Malik broke up with his then-fiancé after four years of relationship. Malik is now ready to be a new dad, together with his girlfriend Gigi Hadid.

Image Source: Youtube/Sweaterperrie Little Mix | Zayne and Perrie

Image Source: Youtube/Sweaterperrie Little Mix | Zayne and Perrie


18. ALANIS MORISSETTE AND RYAN REYNOLDS ARE NOT YOUR PERFECT CANADIAN COUPLE

Before Ryan Reynolds and his wife Blake Lively together walked down the red carpet of Hollywood, Reynolds was crazy over Alanis Morissette when they met at Drew Barrymore’s birthday party and even decided to marry her. However,  She and Reynolds mutually decided to break off their engagement. 

Image Source: Getty Images/Jeff Kravitz | Alanis Morissette and Ryan Reynolds during 2003 MTV Movie Awards

Image Source: Getty Images/Jeff Kravitz | Alanis Morissette and Ryan Reynolds during 2003 MTV Movie Awards


17. SHERYL CROW AND LANCE ARMSTRONG ARE BOTH WINNERS IN THEIR OWN FIELD

The Grammy winner Sheryl Crow met and dated the Tour de France winner Lance Armstrong in 2003. After two years of dating, they got engaged in 2005 but called it off the year after. Armstrong then revealed that Crow was vocal about getting married and having kids. Now, Crow is already content with having two adopted sons.

Image Source: Getty Images/Steve Granitz/Lance Armstrong and Sheryl Crow during GQ Magazine Celebrates the 2005 Men of the Year

Image Source: Getty Images/Steve Granitz/Lance Armstrong and Sheryl Crow during GQ Magazine Celebrates the 2005 Men of the Year


16. JENNIFER LOVE HEWITT AND ROSS MCCALL SHARED TWO YEARS OF ENGAGEMENT

After meeting the set of “Ghost Whisperer'', the singer and actress Jennifer Love Hewitt dated the Scottish actor Ross McCall and the former star couple got engaged in 2007. After two years of being each other’s fiancé, they broke up. Now, Hewitt has two kids with her husband Brian Hallisay. Meanwhile, McCall recently wrote and starred the movie “About Us”.

Image Source: Getty Images/Jeff Kravitz/Jennifer Love Hewitt and Ross McCall during the 2007 Spike TV Scream Awards at The Greek Theater on October 19, 2007 in Los Angeles, California

Image Source: Getty Images/Jeff Kravitz/Jennifer Love Hewitt and Ross McCall during the 2007 Spike TV Scream Awards at The Greek Theater on October 19, 2007 in Los Angeles, California


15. KERRY WASHINGTON AND DAVID MOSCOW ARE NOT EACH OTHER'S HAPPY ENDINGS

Before the actress Kerry Washington married the NFL player Nnamdi Asomugha in 2013 and had three kids together, she was formerly engaged to actor David Moscow in 2005. Washington and Moscow broke up in 2007. The former couple has already moved on as One Last Night actor and has been married to Karen Riotoc since 2014.

Image Source: Getty Images/George Pimentel/David Moscow and Kerry Washington during 2004 Toronto International Film Festival

Image Source: Getty Images/George Pimentel/David Moscow and Kerry Washington during 2004 Toronto International Film Festival


14. SIENNA MILLER AND JUDE LAW CALLED IT QUITS

The American Women actress Sienna Miller and Sherlock Holmes actor Jude Law shared a sweet and shaky relationship from 2003 to 2011 and got engaged in between. Due to issues, the engagement was canceled. Now, Miller is the lovely bride of Lucas Zwirner while Law is expecting a baby as hi wife Philipa Coan is currently pregnant.

Image Source: Getty Images/Gareth Cattermole/Actors Jude Law and Sienna Miller arrive at the World Premiere of "Alfie" at the Empire Leicester Square on October 14, 2004 in London

Image Source: Getty Images/Gareth Cattermole/Actors Jude Law and Sienna Miller arrive at the World Premiere of "Alfie" at the Empire Leicester Square on October 14, 2004 in London


13. JEFFREY DEAN MORGAN AND MARY LOUISE PARKER BECAME OFF-CAM COUPLE

Jeffrey Dean Morgan and Mary Louise Parker were other on-cam couples who became off-cam lovers. They co-starred in the TV series Weeds. Their engagement was broken off in 2008, while the series is still ongoing. Parker, later on, married Billy Crudup but they split in 2003 while The Walking Dead fame has been married to Hilary Burton since last year.

Image Source: Getty Images/Bruce Glikas/Mary Louise Parker and Jeffrey Dean Morgan during "Curtains" Broadway Opening Night - Arrivals - March 22, 2007 at Hirschfeld Theatre in New York City, New York, United States

Image Source: Getty Images/Bruce Glikas/Mary Louise Parker and Jeffrey Dean Morgan during "Curtains" Broadway Opening Night - Arrivals - March 22, 2007 at Hirschfeld Theatre in New York City, New York, United States


12. ROBIN WRIGHT AND BEN FOSTER ARE HAPPILY MARRIED BUT NOT TO EACH OTHER

Robin Wright and Ben Foster worked together in the 2011 film Rampart and yes, they fell in love and got engaged in 2014. Later on, they reportedly broke up after years of sharing ups and downs of romance. Foster has now two kids with “The 70’s Show” actress Laura Prepon while Wright has been married to Clement Giraudet since 2018

Image Source: Getty Images/Jeff Vespa/Actress Robin Wright (L) and actor Ben Foster attend the 72nd Annual Golden Globe Awards at The Beverly Hilton Hotel on January 11, 2015

Image Source: Getty Images/Jeff Vespa/Actress Robin Wright (L) and actor Ben Foster attend the 72nd Annual Golden Globe Awards at The Beverly Hilton Hotel on January 11, 2015

 

11. NO MORE YOU AND I FOR LADY GAGA AND TAYLOR KINNEY 

The Bad Romance singer dated the actor Taylor Kinney for five years. The two are on-cam lovers in the music video of Lady Gaga's song You and I. They dated since then but their engagement was canceled in July 2016. Gaga is now in a relationship with Harvard alum Michael Polanski while Kinney is lip-tight about his love life.

Image Source: Getty Images/John Shearer/Recording artist Lady Gaga (L) and Taylor Kinney arrive at the 2016 Vanity Fair Oscar Party Hosted By Graydon Carter at Wallis Annenberg Center for the Performing Arts on February 28, 2016

Image Source: Getty Images/John Shearer/Recording artist Lady Gaga (L) and Taylor Kinney arrive at the 2016 Vanity Fair Oscar Party Hosted By Graydon Carter at Wallis Annenberg Center for the Performing Arts on February 28, 2016


10. KANYE WEST AND ALEXIS PHIFER WEREN'T ABLE TO RING THE WEDDING BELLS

Before Kanye West married the famous media personality Kim Kardashian, he formerly promised to ring the wedding bells with the fashion designer Alexis Phifer. West and Phifer got engaged in 2006 during an island escapade but they split up later on.

Image Source: Getty Images/Chris Weeks/Alexis Pheiffer, left, and music recording artist Kanye West attend the grand opening of Intermix on September 25, 2007 in Los Angeles, California

Image Source: Getty Images/Chris Weeks/Alexis Pheiffer, left, and music recording artist Kanye West attend the grand opening of Intermix on September 25, 2007 in Los Angeles, California


9. EVAN RACHEL WOOD AND ZACH VILLA SPLIT UP WITH BROKEN MELODIES

It was in 2015 that singer-actress Evan Rachel Wood and musician Zach Villa first met and started producing sweet melodies and love stories. Two years later, they called it quits, leaving their engagement rings behind after rising to stardom as a music duo. The Westworld actress now has a son with her former husband Jamie Bell.

Image Source: Getty Images/Jeff Kravitz/Actress Evan Rachel Wood and actor Zach Villa attend HBO's Official Golden Globe Awards After Party at Circa 55 Restaurant on January 8, 2017

Image Source: Getty Images/Jeff Kravitz/Actress Evan Rachel Wood and actor Zach Villa attend HBO's Official Golden Globe Awards After Party at Circa 55 Restaurant on January 8, 2017


8. GWYNETH PALTROW WASN’T READY TO MARRY BRAD PITT BUT HAS BEEN MARRIED TO GUY NAMED “BRAD”

After three years of being together from 1994 to 1997, fans swooned over the announcement that lovers Gwyneth Paltrow and Brad Pitt called off their engagement. Paltrow then revealed that as a then 22 years old, she wasn’t ready to make that decision yet. Paltrow, later on, married Brad Fulchuk while Pitt has 6 kids with former wife Angelina Jolie.

Image Source: Getty Images/Diane Freed/Brad Pitt and Gwyneth Paltro

Image Source: Getty Images/Diane Freed/Brad Pitt and Gwyneth Paltro


7. PARIS LATSIS PRESENTED 15 RINGS FOR PARIS HILTON

Paris Latsis and Paris Hilton can automatically make us believe in forever just by hearing their name. The two dated for eight months and then in 2005, Latsis presented fifteen rings to Hilton during his marriage proposal. The same year, the Paris and Paris couple ended their engagement. Hilton is now Carter Reum’s girlfriend while Latsis is dating Tamta.

Image Source: Getty Images/Chris Jackson/ocialite Paris Hilton and fiance, Greek shipping heir Paris Latsis are seen front of stage as Madonna performs at "Live 8 London" in Hyde Park on July 2, 2005 in London, England

Image Source: Getty Images/Chris Jackson/ocialite Paris Hilton and fiance, Greek shipping heir Paris Latsis are seen front of stage as Madonna performs at "Live 8 London" in Hyde Park on July 2, 2005 in London, England


6. JENNIFER LOPEZ IN NOT BEN AFFLECK’S GIRL ANYMORE

One of the most picture-perfect celebrity couples was Ben Affleck and Jennifer Lopez, who were then together called “Bennifer”. They started dating in 2002 and got engaged in 2004. TIn the same year, they starred in the film “Jersey Girl”. J. Lo ended her marriage with Marc Anthony in 2011 while Affleck is now Ana de Armas’ boyfriend.

Image Source: Getty Images/Kevin Winter/Actors Ben Affleck and fiancee Jennifer Lopez attend the 75th Annual Academy Awards at the Kodak Theater on March 23, 2003 in Hollywood, California

Image Source: Getty Images/Kevin Winter/Actors Ben Affleck and fiancee Jennifer Lopez attend the 75th Annual Academy Awards at the Kodak Theater on March 23, 2003 in Hollywood, California


5. ROB KARDASHIAN AND BLAC CHYNA WEREN’T SAVED BY THE RING

As we “Keep up with the Kardashians”, let us reminisce about Rob's romance with Black Chyna. Throughout their relationship, they were often spotted showing affection to each other publicly. In 2016, they were engaged and a 7-carat ring was the witness. Sooner they went on a custody battle over their child as they canceled all their wedding plans.

Image Source: Getty Images/Prince Williams/Blac Chyna & Rob Kardashian Visit Onyx Nightclub

Image Source: Getty Images/Prince Williams/Blac Chyna & Rob Kardashian Visit Onyx Nightclub


4. NICOLE KIDMAN CO-STARRED THE DAUGHTER OF LENNY KRAVITZ, HER EX-HUSBANDS-TO-BE

The Happy Feet voice actress Nicole Kidman dated American Women singer Lenny Kravitz from 2002 to 2003. But it was in 2007 that Kidman revealed that they were secretly engaged but broke up eventually. Kidman appeared in Big Little Lies with Zoë, Kravitz’s daughter. Meanwhile, Kravitz’s ex-wife, Lisa Bonet is married to Aquaman actor Jason Momoa.

Image Source: Getty Images/Charley GallayRecording artist Lenny Kravitz (L) and actress Nicole Kidman pose in the green room during the Hollywood Film Awards on November 6, 2016 in West Hollywood, California

Image Source: Getty Images/Charley GallayRecording artist Lenny Kravitz (L) and actress Nicole Kidman pose in the green room during the Hollywood Film Awards on November 6, 2016 in West Hollywood, California


3. DEMI MOORE AND EMILIO ESTEVEZ WERE LOVERS BORN FROM THE BRAT PACK

The Brat Pack members Demi Moore and Emilio Estevez were both 80’s gems as they co-starred in the film St. Elmo Fire. They broke off their almost nuptials in 1986. Moore is currently single after three failed marriages while Estevez was recently spotted hanging out with a lady in a fedora hat, years after his divorce with Paula Abdul.

Image Source: Getty Images/Ron Galella, Ltd./Actor Emilio Estevez and actress Demi Moore attend 'The Early Girl' Off-Broadway Preview Play Performance on October 9, 1986 at Circle Repertory Theatre in New York City

Image Source: Getty Images/Ron Galella, Ltd./Actor Emilio Estevez and actress Demi Moore attend 'The Early Girl' Off-Broadway Preview Play Performance on October 9, 1986 at Circle Repertory Theatre in New York City


2. WINONA RYDER WAS BEHIND JOHNNY DEPP’S TATTOO THAT READ “WINONA FOREVER”

The film Edward Scissorhands bloomed the romance for Johnny Depp and Winona Ryder in 1990. They were set to be married as Depp proposed to Ryder and even got a “Winona Forever” tattoo. However, their relationship ended in 1993. Now, Ryder is in a relationship with Scott Mackinlay Hahn while Depp is facing court battles against his ex-wife Amber Heard

Image Source: Getty Images/Ron Galella, Ltd./Actress Winona Ryder and actor Johnny Depp attend "The Silence of the Lambs" Century City Premiere on February 1, 1991 at Cineplex Odeon Century Plaza Cinemas in Century City, California

Image Source: Getty Images/Ron Galella, Ltd./Actress Winona Ryder and actor Johnny Depp attend "The Silence of the Lambs" Century City Premiere on February 1, 1991 at Cineplex Odeon Century Plaza Cinemas in Century City, California


1. KIEFER SUTHERLAND AND JULIA ROBERTS CANCELLED THEIR WEDDING THREE DAYS BEFORE THE BIG DAY

As then rising acting stars, Keifer Sutherland and Julia Roberts made a powerful Hollywood duo. The Flatliners stars already completed their star-studded guest list for their wedding but three days before they were set to tie the knot, they both made a decision to call it off.

Image Source: Getty Images/Ron Galella, Ltd./Actor Kiefer Sutherland and actress Julia Roberts attend the 48th Annual Golden Globe Awards on January 19, 1991 at Beverly Hilton Hotel in Beverly Hills, California

Image Source: Getty Images/Ron Galella, Ltd./Actor Kiefer Sutherland and actress Julia Roberts attend the 48th Annual Golden Globe Awards on January 19, 1991 at Beverly Hilton Hotel in Beverly Hills, California

Last month, Roberts celebrated 18 years of marriage with her husband Dany Moder together with their three kids. Meanwhile, Sutherland already let go of their past as he was recently spotted in Los Angeles with his long time girlfriend, the actress Cindy Vela

Image Source: Getty Images/Kevin Winter/Actor Kiefer Sutherland and actress Julia Roberts, circa 1990

Image Source: Getty Images/Kevin Winter/Actor Kiefer Sutherland and actress Julia Roberts, circa 1990

It’s a dream come true for two people who are in love to tie the knot. However, love and romance in all angles have their fair share of ups and downs. One common thing about the almost “I do’s” of these former couples is that they didn't think of what-ifs anymore. Instead, they moved on without bitterness.

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