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 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 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... 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, actress, dancer, fashion designer, author and producer.

She is now in 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 Britney Spears Britney Jean Spears, born on December 2, 1981, is an American former singer and actress. She was born in McComb, Mississippi, and 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... 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

6 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 disenrolled and moved to Atlanta in 1997 with Clay Cook. Together, they formed a short-lived two-man band called Lo-Fi Masters.

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

7 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... 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 16 February 1990 in Toronto, Ontario... 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, radio and television personality.
10 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, PayPal, and X (formerly known as Twitter).
The Contenders
11 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 has been married to Hailey for 5 years, I still have a feeling that this marriage won't last.

12 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... 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.

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

14 Taylor Swift Taylor Alison Swift is an American singer-songwriter. She was born on December 13, 1989, in Reading, Pennsylvania. Swift is best known for writing personal songs and has won 13 Grammy Awards... read more

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

Edit: She broke up with Joe Alwyn

15 Dieter Bohlen Dieter Günther Bohlen is a German songwriter, singer, musician, producer, entertainer, and TV personality.
16 Yungblud
17 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.
18 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.

In the late 70s she was known as the lead singer of the Nina Hagen Band, with whom she released two studio albums before pursuing a successful solo... read more
19 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 has had short-lived or on-and-off relationships and has broken off an engagement.

20 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.
21 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 Mezzo-Soprano and spans 4 octaves... read more
22 Jennifer Aniston Jennifer Joanna Aniston is an American actress, producer, and businesswoman. She is the daughter of Greek actor John Aniston and American actress Nancy Dow... read more
23 Kid Rock Robert James Ritchie Sr., known professionally as Kid Rock, is an American singer-songwriter, rapper, musician, record producer, activist, minister and actor.
24 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.
25 Ariana Grande Ariana Grande-Butera (born June 26, 1993) is an American singer, songwriter, and actress. Her four-octave vocal range has received critical acclaim, and her personal life has been the subject of widespread media attention. She has received numerous accolades throughout her career, including two Grammy... 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.

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