Celebrity engagements that didn't work out

At the age of 92, controversial right-wing media mogul and billionaire Rupert Murdoch announced his fifth engagement, to Ann Lesley Smith, 66, a former dental hygienist. Murdoch told the New York Post, "I dreaded falling in love—but I knew this would be my last. It better be. I’m happy." He added, "We’re both looking forward to spending the second half of our lives together."

Well, just weeks after making the announcement, the pair called off their engagement, Vanity Fair reported on April 4, ending "a whirlwind romance that generated headlines around the world.” It remains unclear what happened, and a spokesperson for Murdoch has reportedly declined to comment.

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Avril Lavigne and Mod Sun -

Avril Lavigne said "see you l8er boi" once more, this time to her fiancé of nearly a year, musician Mod Sun. The Canadian singer called off their engagement, which began in March 2022, after being "on and off" for the past few months trying to work things out, reports TMZ. It's unclear what led to the split.

The news, however, came on the heels of photos of Lavigne's romance with Tyga, whom she has been friends with for a while. It all came a surprise to Mod Sun, however, as his rep told TMZ after news of their split, "They were together and engaged as of 3 days ago when he left for tour so if anything has changed that's news to him."

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Jennifer Lopez and Alex Rodriguez -

Jennifer Lopez and Alex Rodriguez had their relationship under a microscope ever since the world-famous singer and the former baseball slugger first started dating in 2017. They announced their engagement in March 2019, had their 2020 wedding postponed due to COVID-19, and on April 15, 2021, the pair revealed in a joint statement that they officially called it quits. "We have realized we are better as friends and look forward to remaining so. We will continue to work together and support each other on our shared businesses and projects. We wish the best for each other and one another’s children. Out of respect for them, the only other comment we have to say is thank you to everyone who has sent kind words and support," they said to TODAY.

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Demi Lovato and Max Ehrich - Demi Lovato and Max Ehrich had a whirlwind pandemic relationship that led to an engagement in July 2020, which was called off a couple months later.

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Paris Hilton and Chris Zylka - Engaged in January 2018, but called it quits in November.

5 / 72 Fotos

Paris Hilton and Paris Latsis - Before there was Paris and Chris, there was Paris and Paris. Engaged from May 2005 to September 2005.

6 / 72 Fotos

Ariana Grande and Pete Davidson - Their whirlwind engagement included tattoos, songs, and even a pet pig, but it only lasted from June to October 2018.

7 / 72 Fotos

Miley Cyrus and Liam Hemsworth - Miley confirmed the engagement in June 2012, but they called it off September 2013. They reunited and even got married in December 2018 but split again less than a year later.

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Rob Kardashian and Blac Chyna - Engaged April 2016 to February 2017 (after one failed reality TV show, a child, and many scandals).

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Emma Roberts and Evan Peters - Engaged from December 2013 to June 2015.

10 / 72 Fotos

Robert Pattinson and FKA Twigs - Engaged from 2015-2016.

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Lenny Kravitz and Nicole Kidman - Engaged from 2002-2003. Kidman reminded everyone of the oft-forgotten relationship when she was asked about how it was working with Zoë Kravitz on 'Big Little Lies.'

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Sophia Bush and Chad Michael Murray - Engaged in 2004, married in 2005, and divorced five months later.

13 / 72 Fotos

Courtney Love and Edward Norton - The stars met on the set of 'The People vs. Larry Flynt' in 1996, and somewhere in their three-year relationship they were reportedly engaged for six months.

14 / 72 Fotos

Kiefer Sutherland and Julia Roberts - Engaged from 1990-1991.

15 / 72 Fotos

Daniel Craig and Satsuki Mitchell - Engaged from 2005-2010.

16 / 72 Fotos

Brad Pitt and Gwyneth Paltrow - Engaged from 1996-1997.

17 / 72 Fotos

Ryan Reynolds and Alanis Morissette - Engaged from 2004-2007.

18 / 72 Fotos

Jennifer Aniston and Tate Donovan - Together from 1995 to 1998, and briefly engaged.

19 / 72 Fotos

Sienna Miller and Jude Law -

Engaged from 2004-2011.

20 / 72 Fotos

Cindy Crawford and Richard Gere - Married from 1991-1995.

21 / 72 Fotos

Jim Carrey and Renée Zellweger - Engaged from 1999-2000.

22 / 72 Fotos

Minnie Driver and Josh Brolin - Engaged from April to October 2001.

23 / 72 Fotos

Billy Bob Thornton and Laura Dern - Engaged in 1998. The relationship ended in 1999.

24 / 72 Fotos

Evan Rachel Wood and Marilyn Manson - Engaged from January to August 2010.

25 / 72 Fotos

Zach Villa and Evan Rachel Wood - Engaged from January to September 2017.

26 / 72 Fotos

Jason Trawick and Britney Spears - Engaged from 2011-2013.

27 / 72 Fotos

Alexis Phifer and Kanye West - Engaged from 2006-2008.

28 / 72 Fotos

Jonny Lee Miller and Angelina Jolie - Married in 1996 and separated by 1997.

29 / 72 Fotos

Rosamund Pike and Joe Wright - Engaged from 2007-2008.

30 / 72 Fotos

Carson Daly and Tara Reid - Engaged from 2000-2001.

31 / 72 Fotos

Rachel Weisz and Darren Aronofsky - Engaged from 2005-2010.

32 / 72 Fotos

Gary Oldman and Uma Thurman - Married from 1990-1992.

33 / 72 Fotos

Katie Holmes and Chris Klein - Engaged from 2003-2005.

34 / 72 Fotos

Hank Azaria and Helen Hunt - Married from 1999-2000.

35 / 72 Fotos

Mark Ronson and Rashida Jones - Engaged from 2003-2004.

36 / 72 Fotos

Sienna Miller and Tom Sturridge - Engaged from 2012-2015.

37 / 72 Fotos

Nicolas Cage and Lisa Marie Presley -

Married in August 2002 and filed for divorce by November 2002.

38 / 72 Fotos

Kate Moss and Pete Doherty - Engaged from April to July 2007.

39 / 72 Fotos

Charlize Theron and Sean Penn - Engaged from 2014-2015.

40 / 72 Fotos

Scott Foley and Jennifer Garner - Married in 2000 and separated by 2003.

41 / 72 Fotos

Johnny Depp and Winona Ryder - Engaged from 1990-1993.

42 / 72 Fotos

Andre Agassi and Brooke Shields - Married from 1997-1999.

43 / 72 Fotos

Nicollette Sheridan and Michael Bolton - Engaged from 2006-2008.

44 / 72 Fotos

Matt Bellamy and Kate Hudson - Engaged from 2011-2014.

45 / 72 Fotos

Nicole Richie and DJ AM -

Engaged from February to December 2005.

46 / 72 Fotos

David Moscow and Kerry Washington - Engaged from 2004-2007.

47 / 72 Fotos

Sheryl Crow and Lance Armstrong - Engaged from 2005-2006.

48 / 72 Fotos

Jennifer Lopez and Ben Affleck - Engaged from 2002-2004. Though it didn't work out back then, the pair reunited and got engaged again in April 2022, and married that July!

49 / 72 Fotos

Emilio Estevez and Demi Moore -

Engaged in 1986, but broken up by 1987.

50 / 72 Fotos

Heather Locklear and Jack Wagner - Engaged from August to November 2011.

51 / 72 Fotos

Zayn Malik and Perrie Edwards - Engaged from 2013-2015.

52 / 72 Fotos

Rose McGowan and Marilyn Manson - Engaged from 1999-2001.

53 / 72 Fotos

Katie Price and Leandro Penna - Engaged in 2012, but for less than a year.

54 / 72 Fotos

Bradley Cooper and Jennifer Esposito - Engaged in October 2006, married in December 2006, and separated by May 2007.

55 / 72 Fotos

Jennifer Love Hewitt and Ross McCall - Engaged from 2007-2008.

56 / 72 Fotos

Carmen Electra and Dennis Rodman - Married November 1998 and filed for annulment nine days later.

57 / 72 Fotos

Rachel Bilson and Hayden Christensen - Engaged from 2008-2010. The couple broke up in 2010, got back together, yet they did not retie their engagement. But since 2017 they are no longer together.

58 / 72 Fotos

Ben Foster and Robin Wright - Engaged January to November 2014. Engaged a second time from January 2015 to August 2015.

59 / 72 Fotos

Jennifer Morrison and Jesse Spencer - Engaged from 2006-2007.

60 / 72 Fotos

Sarah Harding and Tom Crane - Engaged from 2010-2011.

61 / 72 Fotos

Marnie Simpson and Ricky Rayment - Engaged from June to September 2016.

62 / 72 Fotos

Sandra Oh and Alexander Payne - Married in 2003 and separated by 2005.

63 / 72 Fotos

Mark Wright and Lauren Goodger - Engaged from March to August 2011.

64 / 72 Fotos

Nick Cannon and Selita Ebanks - Engaged from May to October 2007.

65 / 72 Fotos

Lucy Mecklenburgh and Mario Falcone - Engaged from 2012-2013.

66 / 72 Fotos

Sam Faiers and Joey Essex - Engaged from 2013-2014.

67 / 72 Fotos

Megan McKenna and Jordan Davies - Engaged in 2015, but broken up less than a year later.

68 / 72 Fotos

Jon Clark and Hannah Elizabeth - Engaged in 2015, but it only lasted a few months.

69 / 72 Fotos

Mary-Louise Parker and Jeffrey Dean Morgan - Engaged from February to April 2008.

70 / 72 Fotos

Kyle MacLachlan and Linda Evangelista -

Engaged from 1995-1998.

71 / 72 Fotos

0 / 72 Fotos

Rupert Murdoch -

1 / 72 Fotos

Avril Lavigne and Mod Sun -

2 / 72 Fotos

Jennifer Lopez and Alex Rodriguez -

Getty Images

3 / 72 Fotos

Demi Lovato and Max Ehrich - Demi Lovato and Max Ehrich had a whirlwind pandemic relationship that led to an engagement in July 2020, which was called off a couple months later.

4 / 72 Fotos

Paris Hilton and Chris Zylka - Engaged in January 2018, but called it quits in November.

5 / 72 Fotos

Paris Hilton and Paris Latsis - Before there was Paris and Chris, there was Paris and Paris. Engaged from May 2005 to September 2005.

6 / 72 Fotos

Ariana Grande and Pete Davidson - Their whirlwind engagement included tattoos, songs, and even a pet pig, but it only lasted from June to October 2018.

7 / 72 Fotos

8 / 72 Fotos

Rob Kardashian and Blac Chyna - Engaged April 2016 to February 2017 (after one failed reality TV show, a child, and many scandals).

9 / 72 Fotos

Emma Roberts and Evan Peters - Engaged from December 2013 to June 2015.

10 / 72 Fotos

Robert Pattinson and FKA Twigs - Engaged from 2015-2016.

11 / 72 Fotos

12 / 72 Fotos

Sophia Bush and Chad Michael Murray - Engaged in 2004, married in 2005, and divorced five months later.

13 / 72 Fotos

Courtney Love and Edward Norton - The stars met on the set of 'The People vs. Larry Flynt' in 1996, and somewhere in their three-year relationship they were reportedly engaged for six months.

14 / 72 Fotos

Kiefer Sutherland and Julia Roberts - Engaged from 1990-1991.

15 / 72 Fotos

Daniel Craig and Satsuki Mitchell - Engaged from 2005-2010.

16 / 72 Fotos

Brad Pitt and Gwyneth Paltrow - Engaged from 1996-1997.

17 / 72 Fotos

Ryan Reynolds and Alanis Morissette - Engaged from 2004-2007.

18 / 72 Fotos

Jennifer Aniston and Tate Donovan - Together from 1995 to 1998, and briefly engaged.

19 / 72 Fotos

Sienna Miller and Jude Law -

Engaged from 2004-2011.

Getty Images

20 / 72 Fotos

Cindy Crawford and Richard Gere - Married from 1991-1995.

21 / 72 Fotos

Jim Carrey and Renée Zellweger - Engaged from 1999-2000.

22 / 72 Fotos

Minnie Driver and Josh Brolin - Engaged from April to October 2001.

23 / 72 Fotos

Billy Bob Thornton and Laura Dern - Engaged in 1998. The relationship ended in 1999.

24 / 72 Fotos

Evan Rachel Wood and Marilyn Manson - Engaged from January to August 2010.

25 / 72 Fotos

Zach Villa and Evan Rachel Wood - Engaged from January to September 2017.

26 / 72 Fotos

Jason Trawick and Britney Spears - Engaged from 2011-2013.

27 / 72 Fotos

Alexis Phifer and Kanye West - Engaged from 2006-2008.

28 / 72 Fotos

Jonny Lee Miller and Angelina Jolie - Married in 1996 and separated by 1997.

29 / 72 Fotos

Rosamund Pike and Joe Wright - Engaged from 2007-2008.

30 / 72 Fotos

Carson Daly and Tara Reid - Engaged from 2000-2001.

31 / 72 Fotos

Rachel Weisz and Darren Aronofsky - Engaged from 2005-2010.

32 / 72 Fotos

Gary Oldman and Uma Thurman - Married from 1990-1992.

33 / 72 Fotos

Katie Holmes and Chris Klein - Engaged from 2003-2005.

34 / 72 Fotos

Hank Azaria and Helen Hunt - Married from 1999-2000.

35 / 72 Fotos

Mark Ronson and Rashida Jones - Engaged from 2003-2004.

36 / 72 Fotos

Sienna Miller and Tom Sturridge - Engaged from 2012-2015.

37 / 72 Fotos

Nicolas Cage and Lisa Marie Presley -

Married in August 2002 and filed for divorce by November 2002.

Getty Images

38 / 72 Fotos

Kate Moss and Pete Doherty - Engaged from April to July 2007.

39 / 72 Fotos

Charlize Theron and Sean Penn - Engaged from 2014-2015.

40 / 72 Fotos

Scott Foley and Jennifer Garner - Married in 2000 and separated by 2003.

41 / 72 Fotos

Johnny Depp and Winona Ryder - Engaged from 1990-1993.

42 / 72 Fotos

Andre Agassi and Brooke Shields - Married from 1997-1999.

43 / 72 Fotos

Nicollette Sheridan and Michael Bolton - Engaged from 2006-2008.

44 / 72 Fotos

Matt Bellamy and Kate Hudson - Engaged from 2011-2014.

45 / 72 Fotos

Nicole Richie and DJ AM -

Engaged from February to December 2005.

Getty Images

46 / 72 Fotos

David Moscow and Kerry Washington - Engaged from 2004-2007.

47 / 72 Fotos

Sheryl Crow and Lance Armstrong - Engaged from 2005-2006.

48 / 72 Fotos

Jennifer Lopez and Ben Affleck - Engaged from 2002-2004. Though it didn't work out back then, the pair reunited and got engaged again in April 2022, and married that July!

49 / 72 Fotos

Emilio Estevez and Demi Moore -

Engaged in 1986, but broken up by 1987.

Getty Images

50 / 72 Fotos

Heather Locklear and Jack Wagner - Engaged from August to November 2011.

51 / 72 Fotos

Zayn Malik and Perrie Edwards - Engaged from 2013-2015.

52 / 72 Fotos

Rose McGowan and Marilyn Manson - Engaged from 1999-2001.

53 / 72 Fotos

Katie Price and Leandro Penna - Engaged in 2012, but for less than a year.

54 / 72 Fotos

Bradley Cooper and Jennifer Esposito - Engaged in October 2006, married in December 2006, and separated by May 2007.

55 / 72 Fotos

Jennifer Love Hewitt and Ross McCall - Engaged from 2007-2008.

56 / 72 Fotos

Carmen Electra and Dennis Rodman - Married November 1998 and filed for annulment nine days later.

57 / 72 Fotos

Rachel Bilson and Hayden Christensen - Engaged from 2008-2010. The couple broke up in 2010, got back together, yet they did not retie their engagement. But since 2017 they are no longer together.

58 / 72 Fotos

Ben Foster and Robin Wright - Engaged January to November 2014. Engaged a second time from January 2015 to August 2015.

59 / 72 Fotos

Jennifer Morrison and Jesse Spencer - Engaged from 2006-2007.

60 / 72 Fotos

Sarah Harding and Tom Crane - Engaged from 2010-2011.

61 / 72 Fotos

Marnie Simpson and Ricky Rayment - Engaged from June to September 2016.

62 / 72 Fotos

Sandra Oh and Alexander Payne - Married in 2003 and separated by 2005.

63 / 72 Fotos

Mark Wright and Lauren Goodger - Engaged from March to August 2011.

64 / 72 Fotos

Nick Cannon and Selita Ebanks - Engaged from May to October 2007.

65 / 72 Fotos

Lucy Mecklenburgh and Mario Falcone - Engaged from 2012-2013.

66 / 72 Fotos

Sam Faiers and Joey Essex - Engaged from 2013-2014.

67 / 72 Fotos

Megan McKenna and Jordan Davies - Engaged in 2015, but broken up less than a year later.

68 / 72 Fotos

Jon Clark and Hannah Elizabeth - Engaged in 2015, but it only lasted a few months.

69 / 72 Fotos

Mary-Louise Parker and Jeffrey Dean Morgan - Engaged from February to April 2008.

70 / 72 Fotos

Kyle MacLachlan and Linda Evangelista -

Engaged from 1995-1998.

71 / 72 Fotos

Celebrity engagements that didn't work out

Rosalía and Rauw Alejandro end engagement after three years together

26/07/23 | StarsInsider

CELEBRITY Engagements

Rosalía and Rauw Alejandro seemed to be a match made in heaven ever since publicly confirming their relationship in August 2021, having even collaborated on a wildly successful EP together that came out on March 24 this year, on which a music video for one of the songs, 'Beso,' revealed that the pair had gotten engaged. But just a few months later, the music powerhouses have called it quits. According to People, while the singers have mutual love and respect for one another, they both agreed to end their engagement. They've both got some ink to remove now, as Rosalía revealed she got "RR" tattooed on her foot, and Rauw had "Rosalía" inked above his navel in a handwritten font.

Every couple months it seems there's another fabulous pair and another dazzling engagement ring tossed in the bin, but celebrity relationships have been fleeting since the dawn of stardom. From nearly tying the knot to weddings you completely forgot, take a look at the brilliant flames that sizzled into silence.