10 celebs who have been engaged 3+ times: Jennifer Lopez, Kaley Cuoco & more

The Flight Attendant actress Kaley Cuoco has recently announced her engagement to Tom Pelphrey (pictured), which marks the fourth time she has been given a ring.

Her first fiancé, addiction specialist Josh Resnik proposed in 2011, but they went their separate ways in 2012 before walking down the aisle.

Kaley had only been dating tennis player Ryan Sweeting for three months when he proposed in September 2013, and they were married from December 2013 to 2015. 

Equestrian Karl Cook proposed on her birthday in December 2017 and they got married in 2018 but announced their separation in 2021.

Brad Pitt has had several high-profile relationships, but did you know he was engaged before becoming famous? The Bullet Train actor intended to marry fellow actress Jill Schoelen, but she ended their relationship when she travelled out of town to film a movie. 

Brad's love life hit the headlines after he embarked on a relationship with Gwyneth Paltrow, to whom he proposed in 1997. Their engagement ended six months later with the Iron Man actress saying she was "totally heartbroken" but adding: "It was the right thing at that time."

Brad proposed to Jennifer Aniston (pictured) in 1999 and they got married in 2000, but their five-year marriage ended in 2005. The actor famously fell in love with his second wife Angelina Jolie on the set of Mr & Mrs Smith, but they didn't get engaged until 2012. They got married in 2014 but she filed for divorce in 2016.

Jennifer Lopez got engaged to waiter-turned-restaurateur Ojani Noa and they got married in 1997, before getting divorced less than a year later. The On The Floor hitmaker then married backup dancer Cris Judd in 2001, but they split nine months later. 

JLo's love story with Ben Affleck (pictured) began in 2002 when they got engaged for the first time, but they called off their wedding in 2004.

She had a whirlwind relationship with her third husband Marc Anthony before they got married in 2004. After their split in 2014, Alex Rodriguez proposed to in 2019 but they called off their engagement in 2021.

Almost 20 years on from their first engagement, JLo and Ben rekindled their romance and he proposed for the second time in 2022. The pair finally walked down the aisle at his Georgia home later that year, but they split in 2024.

Elizabeth Taylor has been engaged ten times (11 if you count the same person twice!) and married eight times. Back in 1949, William Pawley Jr. proposed with a cushion-cut diamond, but they split before walking down the aisle.

She then wed Conrad Hilton Jr. from 1950 to 1951, followed by actor Michael Wilding from 1952 to 1957, and Mike Todd from 1957 to 1958, when he died in a plane crash. Following Mike's death, Elizabeth grew close to his friend Eddie Fisher and they were married from 1959 to 1964. 

Perhaps the Cleopatra actress' most high-profile relationship was with Richard Burton (pictured), whom she married twice – first from 1964 to 1974, and then again in 1975 for less than a year.

Shortly after she ended things for good with Richard, Elizabeth married politician John Warner, but they split in 1982 after six years of marriage. The Little Women star was briefly engaged to Mexican attorney Victor Luna, but she returned his 16-carat sapphire ring in 1984. 

Within six months, she had also broken off an engagement with her ninth fiancé businessman Dennis Stein, who proposed after a two-month romance. 

Her final husband was Larry Fortensky, who she exchanged vows with in 1991, but they ended their five-year marriage in 1996.

Julia Roberts was engaged three times before she married her long-term husband Daniel Moder. The actress was first engaged to her Steel Magnolias co-star Dylan McDermott (pictured), followed by Kiefer Sutherland, with whom she split just days before they tied the knot in 1991.

She then had a whirlwind romance with Lyle Lovett, getting married in 1993 in a small Indiana town after just three weeks of dating. Their love wasn't to be, and they divorced two years later in 1995.

Paris Hilton was engaged twice before walking down the aisle with her husband Carter Reum. 

Aged 20, the socialite got engaged to model Jason Shaw (pictured) but the former couple split the following year before exchanging vows. By 2004, Paris had begun a whirlwind romance with Greek shipping heir Paris Latsis, but they called off their engagement in 2005.

Paris didn't make any plans to marry for several years until she met The Leftovers star Chris Zylka. After less than a year of dating, he proposed in January 2018 before the pair went their separate ways in November that year.

Paris reportedly knew her now-husband Carter for 15 years before their friendship turned romantic in 2019. He proposed with a ring designed by Louis Cartier's great-grandson Jean Dousset in 2021 and they tied the knot eight months later.

Two of Kim Kardashian's weddings featured on Keeping Up with the Kardashians, but she was married before she started the hit reality TV show. 

When she was 19, Kim wed producer Damon Thomas, but their marriage ended after four years in 2004.

Professional basketball player Kris Humphries (pictured) proposed to Kim with a Lorraine Schwartz ring in May 2011 after less than a year of dating. They tied the knot in August, but she filed for divorce after just 72 days.

Kanye West pulled out all the stops for his proposal in 2013, offering her a 15-carat ring when he popped the question inside a baseball stadium in San Francisco. They tied the knot in Italy in 2014 but split in 2022.

Three sparkling rings have been given to Kate Hudson over the years, starting with Chris Robinson. Kate was 20 when she began her fast-paced relationship, and she said on Alex Cooper’s podcast, Call Her Daddy: "We were engaged in four months, married at nine months. Then, [after] three years, I wanted to have a baby. Then it started to do that downward spiral." 

They ended their seven-year marriage in 2007, and Kate went on to get engaged to Matt Bellamy (pictured) in 2011, but they split in 2014 before walking down the aisle. 

The How to Lose a Guy in 10 Days actress had been friends with her current fiancé Danny Fujikawa for 15 years and dated him for four years before he proposed in 2021. 

Drew Barrymore was just 16 when she first got engaged to Leland Hayward III. The pair called things off months later, and she went on to have a whirlwind romance with actor Jamie Walters whom she later described as a "good guy."  He proposed after three months of dating in 1992, but they split the following year.

At age 19, the Never Been Kissed actress married 31-year-old Jeremy Thomas (pictured) after six weeks of dating, but the marriage broke down after less than one month. She later told the Star: "I realized my mistake the day I married him."

Tom Green was Drew's fourth fiancé and the couple got married in Malibu in 2001 before splitting in 2002.

Finally, Drew married her ex-husband Will Kopelman in 2012 and they welcomed two kids before separating in 2016.

Despite getting engaged five times, Johnny Depp only got married twice. The Pirates of the Caribbean star's first wife was makeup artist Lori Anne Allison, whom he married aged 20 in 1983. The couple called it quits after two years of marriage. 

There were rumours the actor was engaged to Sherilyn Fenn, but that was never confirmed. He then proposed to Dirty Dancing's Jennifer Grey (pictured) two weeks after they met, but nine months later, she left him a breakup note in his hotel room.

Winona Ryder was his third fiancé, with Johnny proposing just five months after their first date. They dated for three years before splitting in 1993.

Despite a long-term relationship, Johnny never married Vanessa Paradis. Shortly after their split, Johnny went public with his relationship with Amber Heard and they got engaged in January 2014. They married in two celebrations in 2015 but split in 2016 and went through a very high-profile court battle.