Top 10 Living Celebrities with the Messiest Love Life

These celebrities are notorious for having had numerous high-profile relationships or marriages, or just not being able to stay in committed relationships. Maybe they're unwilling to commit or they just haven't found "the one" yet.

Some of these celebrities are also quite young, so they have time anyway. Deceased celebrities who married multiple times, such as Elizabeth Taylor, won't be counted here.

1. Drake

   

   Aubrey Drake Graham (born October 24, 1986) is a Canadian rapper, singer, songwriter, record producer, and actor from Toronto. He first gained public attention as an actor on the Canadian series Degrassi: The Next Generation before launching a music career. Drake's become one of the world's best-selling... read more

   Does this really need an explanation?

2. Leonardo DiCaprio

   

   Leonardo Wilhelm DiCaprio (born November 11, 1974) is an American actor and film producer. Known for his work in biopics and period films, he's received numerous accolades, including an Academy Award, a British Academy Film Award, and three Golden Globe Awards. As of 2019, his films have grossed over... read more

   Up to this point, we all know Leo's relationship cycle, unless he decides to pull off a George Clooney and get married at 50. We'll wait and see.

   Has a girlfriend in her early 20s, breaks up with her before she turns 25, repeat.

3. Jennifer Lopez

   

   Jennifer Lynn Lopez, also known as J. Lo, is an American singer, songwriter, actress, dancer, fashion designer, author, producer, and businesswoman. She's regarded as one of the most influential entertainers of her time, credited with breaking barriers for Latino Americans in Hollywood and helping propel... read more

   She is now in her fourth marriage with Ben Affleck. Let's see how long it lasts.

   Edit: Bennifer broke up again.

4. Avril Lavigne

   

   Avril Ramona Lavigne (born September 27, 1984) is a Canadian singer-songwriter and actress. At age 14, she won a radio contest singing with Shania Twain, performing before a large arena crowd. By age 16, she had signed a two-album recording contract with Arista Records, reportedly worth over $2 million.... read more

   She just broke off her engagement with Mod Sun, and recently she's been spotted kissing Tyga. Why would she date that creep?

5. John Mayer

   

   John Clayton Mayer is an American singer-songwriter, guitarist, and record producer. Born in Bridgeport, Connecticut, Mayer attended Berklee College of Music in Boston but left before graduating. He moved to Atlanta in 1997 with Clay Cook, where they formed a short-lived two-man band called Lo-Fi Masters... read more

   Not only has he dated so many famous women, but he has also made himself a reputation for being a bad ex-boyfriend.

6. Britney Spears

   

   Britney Jean Spears (born on December 2, 1981, in McComb, Mississippi) is an American former singer and actress. She was raised in Kentwood, Louisiana. As a child, she performed acting roles in stage productions and television shows, such as The Mickey Mouse Club, before signing with Jive Records in... read more

   From her high-profile relationship with fellow superstar Justin Timberlake to her 55-hour marriage with a childhood friend, to her highly publicized divorce and child custody battle with Kevin Federline, Britney Spears has definitely had a messy love life. Even though her current marriage seems more stable, she is still feuding with Kevin Federline about their kids' education, among other things.

   Edit: she's getting divorced again

7. Scarlett Johansson

   

   Scarlett Johansson (born November 22, 1984) is an American actress, model, and singer. She made her film debut in North (1994).

   Johansson is considered one of Hollywood's modern sex symbols and has frequently appeared on published lists of the sexiest women in the world.... read more

8. The Weeknd

   

   Abęl Makkonen Tesfaye, known professionally by his stage name The Weeknd, is a Canadian singer, songwriter, and record producer. He was born on February 16, 1990, in Toronto, Ontario. He began uploading music to YouTube in 2010 and later released several studio albums, including Kiss Land, Beauty Behind... read more

   Most of his songs reflect how messy his love life is, but it seems like he is trying to break out of that image lately.

9. Nick Cannon

   

   Nicholas Scott "Nick" Cannon is an American rapper, actor, comedian, entrepreneur, record producer, and radio and television personality. He began his career as a teenager on the Nickelodeon sketch comedy show All That. Cannon later hosted America's Got Talent, created the MTV comedy series Wild 'N Out... read more

10. Justin Bieber

    

    Justin Drew Bieber (born March 1, 1994) is a Canadian singer, songwriter, and record producer. He currently resides in Ontario, Canada, and is Christian. He is the son of Pattie Mallette, an author.

    Justin Bieber is best known for his songs "Baby" and "What Do You Mean?" As of mid 2025, 11 of... read more

    Even though he has been married to Hailey for 5 years, I still have a feeling that this marriage won't last.

The Newcomers
11. ?

    Ariana Grande

    

    Ariana Grande‑Butera (born June 26, 1993) is an American singer, songwriter, and actress. Her four‑octave vocal range has earned widespread critical praise, and her personal life continues to attract significant media attention. She has received numerous honors, including two Grammy Awards, a Brit Award... read more

    She's infamous for being a home-wrecker and has broken one engagement and one marriage. Let's see how long her relationship with Ethan Slater will last.

12. ?

    Machine Gun Kelly

    

    Colson Baker, better known by his stage names MGK and Machine Gun Kelly, is an American rapper and actor from Cleveland, Ohio. He first gained attention for his rapid fire delivery and releases such as Lace Up in 2012, and he has since put out multiple studio albums. In the 2020s, he shifted toward... read more

The Contenders

13. Elon Musk

    

    Elon Reeve Musk (born June 28, 1971) is a technology entrepreneur, investor, and engineer best known for being the CEO of Tesla, SpaceX, and X (formerly known as Twitter). He co-founded PayPal, which was acquired by eBay in 2002.... read more

14. Chris Brown

    

    Christopher Maurice "Chris" Brown (born May 5, 1989) is an American singer, songwriter, dancer, and actor. Born in Tappahannock, Virginia, he participated in his church choir and several local talent shows from a young age. He gained international notoriety in 2009 for his physical assault of singer... read more

    Dated and assaulted Rihanna, dated Karrueche Tran on and off, and fathered a child with another woman. Went back with Rihanna, got a restraining order from Karrueche Tran, received more accusations of rape, assault, and domestic violence. In other words, Breezy is a terrible boyfriend, and we all know it by now.

15. Taylor Swift

    

    Taylor Alison Swift is an American singer-songwriter, born on December 13, 1989, in Reading, Pennsylvania. She developed a strong interest in country music around the age of nine after watching a Faith Hill documentary. Swift moved to Nashville as a teenager and, after signing with RCA Records, began... read more

    She used to have a messy love life, but she was in a stable relationship for six years, so that's why I did not include her at first.

    Edit: She broke up with Joe Alwyn and recently got engaged to Travis Kelce. Let's see how long it lasts.

    Yes, and she writes about her boyfriends and breakups in her songs. How rude and really offensive.

16. Pete Davidson

    

    Pete Davidson is an American comedian and actor. He was a cast member on Saturday Night Live from 2014 to 2022. Davidson has also appeared on the MTV shows Guy Code, Wild 'n Out, and Failosophy, and starred in the semi-autobiographical film The King of Staten Island.

    He is mostly known for being a rebound boyfriend. His most famous exes include Ariana Grande (to whom he was engaged) and Kim Kardashian.

17. Dieter Bohlen

    

    Dieter Günther Bohlen is a German songwriter, singer, musician, producer, entertainer, and television personality. He is best known as a member of the pop duo Modern Talking. Bohlen has also served as a judge on Deutschland sucht den Superstar, the German version of American Idol.

18. Yungblud

    

19. Nikki Sixx

    

    Nikki Sixx is an American musician, songwriter, radio host, and photographer, best known as the co-founder, bassist, and primary songwriter of the band Mötley Crüe. He also founded the band Sixx:A.M. and authored several books, including The Heroin Diaries. Sixx has been an influential figure in the... read more

20. Nina Hagen

    

    Catharina Hagen, better known by her stage name Nina Hagen, is a German singer-songwriter and actress born on March 11, 1955, in former East Berlin. She gained fame in the late 1970s as the lead singer of the Nina Hagen Band. With the band, she released two studio albums before starting a successful... read more

21. Meg Ryan

    

    Margaret Mary Emily Anne Hyra, known professionally as Meg Ryan, is an American actress and producer. She rose to prominence in the late 1980s and early 1990s with popular romantic comedies such as When Harry Met Sally… and Sleepless in Seattle. Ryan has received multiple award nominations and later... read more

    She had a stable love life until the early 2000s when she had an affair with Russell Crowe while married to Dennis Quaid. Since then, she has had short-lived or on-and-off relationships and has broken off an engagement.

22. Drew Barrymore

    

    Drew Blythe Barrymore is an American actress, producer, director, author, model, and entrepreneur. She is a member of the Barrymore family of actors and the granddaughter of legendary actor John Barrymore. She became widely known as a child actress for her role in E.T. the Extra-Terrestrial.

23. Miley Cyrus

    

    Miley Ray Cyrus (born Destiny Hope Cyrus), known professionally as Miley Cyrus, is an American singer, songwriter, and actress. She was born on November 23, 1992, in Franklin, Tennessee, to Tish Cyrus and Billy Ray Cyrus. Her voice type is popularly described as a lyric mezzo soprano, with a vocal range... read more

24. Jennifer Aniston

    

    Jennifer Joanna Aniston is an American actress, producer, and businesswoman. She's the daughter of Greek actor John Aniston and American actress Nancy Dow. Aniston rose to worldwide fame portraying Rachel Green on the sitcom Friends, earning a Primetime Emmy Award, a Golden Globe Award, and a Screen... read more

25. Kid Rock

    

    Robert James Ritchie Sr., professionally known as Kid Rock, is an American singer-songwriter, rapper, musician, record producer, and actor. He has blended genres such as rock, hip-hop, and country throughout his music career. Kid Rock is also known for his outspoken personality and activism.... read more

26. John Mellencamp

    

    John J. Mellencamp (born October 7, 1951), who has also performed under the names Johnny Cougar, John Cougar, and John Cougar Mellencamp, is an American singer-songwriter. He is known for his brand of heartland rock, which focuses on traditional instruments and working-class themes. His music gained... read more

27. Brad Pitt

    

    William Bradley "Brad" Pitt (born December 18, 1963) is an American actor and producer. He has received a Golden Globe Award, a Screen Actors Guild Award, and three Academy Award nominations for acting, in addition to three more nominations and one win as a producer under his company, Plan B Entertainment.... read more