Getty Images

Some Hollywood celebs are known to be serial daters, and some of them have even managed to get engaged more than once! While a proposal is supposed to be a once in a lifetime event, some stars have had to give being engaged a shot multiple times before finding "the one." Engagements get called off all the time, especially in Hollywood. After the magic question "Will you marry me?" was asked, some celebs didn't get the chance to walk down the aisle because they called it quits before the wedding. Meanwhile, others actually tied the knot but the marriage sadly just didn't last and they were forced to try again. 

More from MamásLatinas: 14 Celebrity couples who have called off their weddings

Putting a ring on it doesn't automatically mark the start of a happily ever after for some people, and some famosos have had to be fiancés and fiancees more than once before finding that forever love. It's admirable to see that even though one relationship didn't work for them, they got right back out into the dating world and found love again--and even another diamond. 

Celebrities like Jennifer LopezMariah CareyMarc Anthony continue to give love a chance after they have been engaged multiple times, and they show no signs of slowing down any time soon. After all, who could resist the opportunity to marry some of the most beautiful and attractive people in the world? Click through to see which celebs have said "yes" more than once, and which male celebs have popped the question time and time again. 

J. Lo is the queen of engagements! 1

J. Lo is the queen of engagements!

Splash News

Jennifer Lopez revealed to James Corden that she's been proposed to five times in her lifetime! FIVE! While most people find it difficult to even find a date, the singer said she turned down a few proposals, but eventually ended up walking down the aisle three times. 


Sofia Vergara called off her engagement to Nick Loeb. 2

The Modern Family actress was engaged to Nick Loeb before she married Joe Manganiello


Marc Anthony has been down the engagement road before. 3

The singer has been married a total of four times! He proposed to Jennifer Lopez soon after his divorce to Dayana Torres became final in 2004, and he proposed to Shannon De Lima the same year he divorced J.Lo. 

Naya Rivera got engaged twice in less than one year. 4

The Glee actress announced her engagement to Big Sean in October 2013, and after calling off their wedding she tied the knot with Ryan Dorsey in July 2014.


Adamari Lopez gave love another chance. 5

After her marriage to Luis Fonsi came to an end, Adamari got engaged to Toni Costa.


Mariah Carey knows how to end an engagement. 6

Mariah was previously married to Tommy Mottola and Nick Cannon, who is the father of her twins. In January 2016 she announced she was engaged to James Packer but the pair called it quits later that year. She got to keep the 35-carat ring and reportedly sold it for $2.1 million. 


We've watched two of Kim Kardashian's proposals on TV. 7

Kris Humphries proposed to Kim and the moment was shared on Keeping Up With the Kardashians, but that relationship famously ended a few months after the wedding. When Kanye West popped the question, the world got the see the over-the-top proposal on the reality show. Prior to those relationships, Kim was also married to record producer Damon Thomas when she was 19.

Kat Von D has had her fair share of proposals. 8

The makeup mogul was married to her Ink Master costar, Oliver Peck, but when that relationship ended she moved on to get engaged to Jesse James in 2011. When that ended, she was set to marry DJ Deadmau5 but the pair called it quits. In 2018, she got married to musician Rafael Reyes.


Lady Gaga has received some awesome diamond rings. 9

The singer got engaged to actor Taylor Kinney in February 2015, but they called it quits before they ever got the chance to walk down the aisle. He gave her a gigantic diamond, heart-shaped ring. After that relationship came to an end, it was reported that she got engaged to Christian Carino in November 2017.

Brad Pitt loves his leading ladies. 10

Brad Pitt loves his leading ladies.

Splash News

The actor was engaged to Gwyneth Paltrow in the 1990s. He then married Jennifer Aniston but that relationship ended in 2005, and he began dating Angelina Jolie--whom he married in August 2014.


Paris Hilton has been a fiancee multiple times. 11

The former reality TV star was engaged to Jason Shaw in 2002 and years after that ended, Paris Latsis proposed to her in 2005. Almost a decade later, Paris got engaged to actor Chris Zylka in January 2018.

Tom Cruise gave marriage a shot three times. 12

Tom Cruise gave marriage a shot three times.

Splash News

Tom was married to Mimi Rogers from 1987 until 1990. Later that year, he married Nicole Kidman after meeting her on the set of a movie they worked in together. He famously married Katie Holmes in 2005, but the pair eventually also called it quits.


Gwyneth Paltrow has been engaged to two Brads. 13

The Iron Man actress got engaged to Brad Falchuk in January 2018. Prior to that relationship, she was married to Coldplay's Chris Martin and was also engaged to Brad Pitt in the 90s.  

Eva Longoria found her happy ending. 14

Eva Longoria found her happy ending.

Splash News

Two years after her divorce from her first husband, Tyler Christopher, Eva said yes to Tony Parker in 2006, but they got divorced in 2010. She announced her engagement to Jose Bastón in Decemeber 2015 and they married in May of the following year. 


Tommy Mottola has been lucky in love. 15

After his first marriage to Lisa Clark, Tommy married Mariah Carey at the height of her career. The pair later divorced and he married Thalia--and the couple has been together ever since. 

Drew Barrymore got engaged super young! 16

Drew got engaged to Leland Hayward when she was just 16! She was also engaged to Jamie Walters in the 1990s and married Tom Green in 2000. In 2012, she announced her engagement to Will Kopelman, but the pair have since called it quits after four years of marriage.


Halle Berry has walked down the aisle three times. 17

Olivier Martinez, Eric Benét and David Justice all put a ring on the Catwoman actress. 

Jenni Rivera's love life was heartbreaking. 18

Jenni Rivera's love life was heartbreaking.

Splash News

After she had a tumoultous relationship with her first husband José Trinidad Marín, she gave marriage a second chance with Juan Lopez. That marriage ended in 2003 after he was sent to jail and she married Esteban Loaiza in 2010, but they called it quits just months before her death. 


Sandra Bullock 19

Sandra Bullock

Getty Images

Before marrying ex-husband Jess James in 2005, Sandra was previously engaged to actor Tate Donovan, whom she met in 1992. 

Christina Aguilera has been engaged for quite some time. 20

The singer has been engaged to Matt Rutler since 2014! She's been dating him since 2010, after she called it quits with first husband Jordan Bratman.