15 Celebs Who've Proposed More Than Once

Multiple marriages, called-off engagements, cheating scandals and more; relationship drama in Hollywood is always swirling. It’s also no surprise when fans see celebrity couples make up, break up or “put a ring on it.” What is surprising is when celebrities decide to marry a “non-famous” after their own fame comes. Although, it seems as though their track records tend to be a bit more successful and less tabloid-friendly.

But what about the celebrities that seem to only date other celebrities? Or, even further, get engaged and get married to other celebrities (plural form, of course). Who has proposed to others in the spotlight? Who has proposed to both movie stars and pop stars alike? Take the plunge and check out these 15 celebrities that have proposed to more than one woman while finding out how successful the engagement actual was!

15 Ben Affleck


Gone Girl actor, Ben Affleck, proposed to two of Hollywood’s favorite leading ladies, Jennifer Lopez and Jennifer Garner. Although, he only walked down the aisle with one. Lopez and Affleck called off their engagement in 2004, according to MTV. And not too long after the cancellation, merely a year, Affleck proposed to another famous Jennifer, star of the hit ABC show Alias, in 2005. Unfortunately, they’ve recently, after 10 years of marriage and three children, announced their divorce.

14 Frank Sinatra

via Huffington Post

Frank Sinatra was known for his silky voice and crooning persona, but he was also known for his marriages. Married four times, with two wives being powerful, Hollywood women; he apparently had quite the way with the ladies. Sinatra married Earthquake and Show Boat star, Ava Gardner, in 1951 but ten years after their divorce he proposed and married Rosemary’s Baby leading lady, Mia Farrow. Their relationship ended in 1968.

13 Tom Cruise


Another Hollywood heartthrob and leading man decided to propose and marry two talented and beloved beauties. Tom Cruise and Nicole Kidman were married in 1990, both were in their 20’s, and decided to adopt two children. Unfortunately after 10 years together, the pair decided to end their marriage. But in 2005 Cruise met Katie Holmes and everything changed. Who doesn’t remember him jumping up and down in love on Oprah’s couch? Holmes was married to Mr. Mission Impossible until their divorce in 2012.

12 Ashton Kutcher


Ashton Kutcher rose to fame as Michael Kelso in the Fox sitcom That ‘70s Show, alongside now-wife, Mila Kunis. But before those two became one and had a baby girl, Kutcher was in a high-profile relationship and marriage with GI Jane herself, Demi Moore. The pair were married for nearly a decade before calling it quits. Kutcher and Kunis began dating in 2012, became engaged in 2014 and welcomed their baby girl, Wyatt, in the same year. On July 4th 2015, the 70’s co-stars had a “secret” wedding with only some of their closest friends and family in attendance.

11 Sean Penn


Sean Penn has been engaged to four Hollywood women – but he only married two. According to Mirror, he was first engaged to Elizabeth McGovern, who starred alongside him in Racing with the Moon. After the engagement was broken, Penn met Madonna and the two wed in 1985. Once their divorce was finalized he began a relationship with Robin Wright, also known as Jenny from Forrest Gump. The two split in 2009. Most recently, the Mystic River star fell into a relationship and broken engagement with South African beauty, Charlize Theron.

10 Kayne West


Before Kayne gave Kim Kardashian one of the most lavish proposals the world has ever seen, he was engaged to designer, Alexis Phifer. They were engaged for a year and a half before deciding to part ways. But after beginning a relationship with reality queen, Kardashian, he decided to take the plunge and make it to the aisle this time. The two are awaiting the arrival of their second child, a boy, December 2015.

9 Brad Pitt


Brad Pitt is a hunk of a leading man, arguably one of the most talented actors in the business but also known for his two – very high-profile – relationships. Friends star and America’s sweetheart, Jennifer Aniston, was his first wife. According to MTV, Pitt proposed to Aniston in 1998 with a $500,00 Silvia Damiani ring. After the two split, he was seen shortly after with his Mr. and Mrs. Smith co-star who would soon become his partner for nearly seven years (with six children) before announcing an engagement. That co-star is obviously the beautiful, Angelina Jolie.

8 Michael Bubé

via Huffington Post

Mr. Bublé has had not one but three celebrity engagements – with only one turning into a marriage. Although not as publicized as his later relationships, he was first engaged to actress Debbie Timuss; his hit song “Home,” details their relationship. But then, he met actress Emily Blunt. Unfortunately, they ended their engagement in 2008. Bublé then met his now-wife Argentinian actress, Luisana Lopilato. The couple married in 2011 and have one son together, Noah, and as of summer of 2015 are expecting their second baby.

7 Ryan Reynolds


Soon to be playing Deadpool in the film inspired by the Marvel Comic, this Hollywood hunk has also been engaged to three celebrities – but said “I do’s” to only two. Reynolds proposed to singer, Alanis Morissette in 2004 but, according to People, they called off their engagement just a year later. Although his second engagement to Scarlett Johansson turned into a marriage, it also ended completely when they divorced but left their relationship with love and kindness. Reynolds moved on to blonde bombshell and actress, Blake Lively. The two wed in 2012 and welcomed their first daughter in 2014.

6 Eddie Fisher

via Tributes

Eddie Fisher was one of the most popular singers in the 1950’s but he was also famous for his five wives and the scandal between the first two – which were two of Hollywood’s hottest young women. In 1955 Fisher married triple-threat, Debbie Reynolds, whom he had two children with. Unfortunately their marriage ended when Fisher had an affair with Reynolds’ best friend, Elizabeth Taylor. The teen heartthrob and pop icon went on to marry singer and actress, Connie Stevens, former beauty queen, Terry Richard, and finally, businesswoman, Betty Lin, which is the only one that didn’t end in divorce – staying married until his passing in 2010.

5 Jesse James


Jesse James has been engaged five times and married twice – with four of those women being in the spotlight for various reasons. According to She Knows, his second wife was Janine Lindemulder, known for her career in the adult film industry. His third wife was Oscar award-winning actress, Sandra Bullock to whom he was married to for five years before their separation. James moved on to famous tattoo artistic, Kat Von D, and they were engaged for a bit over a year before ending the relationship. Most recently, he became engaged to professional drag racer, Alexis DeJoria, and they married in 2013.

4 Nick Cannon


America’s Got Talent host, Nick Cannon, has had two leading ladies that he’s gotten down on one knee for. First was Selita Ebanks, model and Victoria’s Secret Angel. They ended their engagement after five months. Then comes iconic singer, Mariah Carey, who Cannon married in the Bahamas in 2008. Unfortunately, he filed for divorce in December of 2014 after six years of marriage and two children together.

3 Billy Joel


The iconic singer has also been married a handful of times. But only twice did he propose to famous ladies. Model, Christie Brinkley, was his first Hollywood wife but they divorced in 1994. His third wife, Katie Lee, is known for her work as a food critic and hosting Bravo’s first season of Top Chef. These two decided to split in 2009. Joel decided to stay away from the spotlight with his fourth wife, he is currently married to Alexis Roderick and they’re expecting their first child in 2015.

2 Jude Law


Leading man, Jude Law, has also had a couple of engagements – one leading to marriage – with actresses. His first wife, Sadie Frost, he met while on set of their film, Shopping, they married in 1997. A little over a year after their divorce Law proposed to Sienna Miller, whom he filmed Alfie with, on Christmas Day 2004. There were rumors of his affair with the nanny of his children and her affair with Daniel Craig. Their engagement was called off two years later in 2006.

1 Emilio Estevez


Fans loved him in The Breakfast Club and The Mighty Ducks, and there were two famous women who loved him enough to say yes to a proposal. He had a brief engagement to actress, Demi Moore, which ended before they made the final leap to walk down the aisle. But his engagement to singer and dancer, Paula Abdul, led to a wedding in 1992 – and subsequent divorce in 1994.

Sources: mtv.com, foxnews.com, people.com, huffingtonpost.com

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