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 anyways. Deceased celebrities who married multiple time such as Elizabeth Taylor won't be counted here.
The Top Ten
1 Drake Aubrey Drake Graham, known professionally as Drake, is a Canadian rapper, singer, songwriter, record producer and actor, born on October 24, 1986 in Toronto, Canada. He started his career on Canadian reality show "Degrassi: The Next Generation".

Does this really need 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 is the recipient of numerous accolades, including an Academy Award, a British Academy Film Award, and three Golden Globe Awards. As of 2019, his films have grossed over $7.2 billion worldwide, and he has been placed eight times in annual rankings of the world's highest-paid actors. ...read more.

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

Has a girlfriend of 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, actress, dancer, fashion designer, author and producer.

She's now at her 4th marriage with Ben Affleck, let's see how long it will last.

4 Avril Lavigne Avril Ramona Lavigne is a Canadian–French singer-songwriter and actress. By the age of 15, she had appeared on stage with Shania Twain; by 16, she had signed a two-album recording contract with Arista Records worth more than $2 million.

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

5 Scarlett Johansson Scarlett Johansson (born November 22, 1984) is an American actress, model, and singer. She made her film debut in North. Johansson is considered one of Hollywood's modern sex symbols, and has frequently appeared in published lists of the sexiest women in the world. As of February 2017, she is the highest-grossing actress of all time in North America, with her films making over $3.6 billion. She has appeared in many movies such as 2014's Lucy or 2013's Under The Skin. She also plays the character ‘Black Widow’ in Marvel movies such as Ironman 2, The Avengers, Avengers: Age of Ultron, Avengers: Infinity War, and Avengers: Endgame
6 Britney Spears Britney Jean Spears (born December 2, 1981) is an American actress and former singer who was born in McComb, Mississippi, and grew up in Kentwood, Louisiana. She performed acting roles in stage productions and television shows like "The Mickey Mouse Club" as a child before signing with Jive Records in 1997 and going on to become a pop superstar and one of the most famous female pop singers of all time. She is best known for her songs such as "Toxic", "...Baby One More Time", "Circus", "I'm A Slave 4 U", "Oops!... I Did It Again", "Work B****", "Womanizer" and "Till' The World Ends".

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 definitely had a messy love life. Even though her current marriage seems more stable, she's still feuding with Kevin Federline about their kids' education, among other things.

7 John Mayer

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

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 16 February 1990 in Toronto, Ontario. He used to upload songs on YouTube in 2010, now he has 3 studio albums Kiss Land, Beauty Behind The Madness and Starboy. He has won 3 Grammy awards and 9 Juno Awards

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

9 Elon Musk Elon Reeve Musk (born June 28, 1971) is a technology entrepreneur, investor, and engineer who is best known for being the CEO of companies such as Tesla, SpaceX, and PayPal.
10 Nick Cannon Nicholas Scott "Nick" Cannon is an American rapper, actor, comedian, entrepreneur, record producer, radio and television personality.
The Contenders
11 Pete Davidson Pete Davidson is an American actor and comedian. He is a cast member on Saturday Night Live. Davidson has also appeared on the MTV shows Guy Code, Wild 'n Out, and Failosophy.

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

12 Dieter Bohlen Dieter Günther Bohlen is a German songwriter, singer, musician, producer, entertainer, and TV personality.
13 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. ...read more.
14 Yungblud
15 Chris Brown Christopher Maurice "Chris" Brown (born May 5, 1989) is an American singer, songwriter, dancer and actor. Born in Tappahannock, Virginia, he was involved in his church choir and several local talent shows from a young age. He is most well known for his physical assault towards the singer Rihanna in 2009. He is also known for many hit singles, such as "Kiss Kiss", "Run It!", "Forever", "Deuces", "Look At Me Now", "Loyal", "Ayo", and "Back to Sleep".

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, got more accusations of rape, assault and domestic violence, etc. In other words, Breezy is a terrible boyfriend and we all know it by now.

16 Meg Ryan Margaret Mary Emily Anne "Meg" Hyra, known professionally as Meg Ryan, is an American actress and producer.

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 had short-lived or on-and-off relationships and broke off an engagement.

17 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 John Barrymore. She achieved fame as a child actress with her role in E.T. the Extra-Terrestrial.
18 Miley Cyrus Miley Ray Hemsworth (born Destiny Hope Cyrus), known 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 Mezzo-Soprano and has 4 octaves. She became a teen idol starring as the character Miley Stewart in the Disney Channel television series Hannah Montana in 2006. After that Miley had numerous worldwide hits, such as ''Party in the USA'', '' We Can’t Stop'', and ''Wrecking Ball''. On December 23, 2018 she got married to Australian actor Liam Hemsworth, but they divorced shortly after.
19 Taylor Swift Taylor Alison Swift is an American singer-songwriter. She was born on December 13, 1989 in Reading, Pennsylvania. She is best known for writing personal songs and for having won 11 Grammys. She became interested in country music when she was around 9 years old, and after watching a documentary about Faith Hill, Swift felt that she should go to Nashville to begin a country music career. She then signed a contract with RCA Records and began to write songs.

She used to have a messy love life, but she's been in a stable relationship for 6 years so that's why I did not include her at first.

20 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.
21 Jennifer Aniston Jennifer Joanna Aniston is an American actress, producer, and businesswoman. The daughter of Greek actor John Aniston and American actress Nancy Dow, Aniston gained worldwide recognition for portraying Rachel Green on the popular television sitcom Friends, a role which earned her a Primetime Emmy Award, a Golden Globe Award, and a Screen Actors Guild Award.
22 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 author Pattie Mallette. ...read more.

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

23 John Mellencamp
24 Kid Rock Robert James Ritchie Sr., known professionally as Kid Rock, is an American singer-songwriter, rapper, musician, record producer, activist, minister and actor.
25 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 in acting categories and received three further Academy Award nominations, winning one, as producer under his own company Plan B Entertainment. ...read more.
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