20+ Celebrities with the Most Number of Relationships

In the glamor of Hollywood, many celebrities are seen dating co-stars and other professionals. Some of the celebrities Cheated on their partner. Their relationships have always been a fascination for the public. You never know which actor is dating whom until they disclose it. This list of the top 40 celebrities with the most relationships includes many high-profile marriages.

Drew Barrymore

Drew-Barrymore

The list of the highest number of relationships was topped by Drew Barrymore, who had numerous partners and she got married to 3 of them. Her first relationship was with Corey Feldman at the age of 14. After a few years, she married Tom Green. This long list includes the names Rick Salomon, Leland Hayward, David Arquette, Jeremy Thomas, and Eric Erlandson.

She got hitched to another actor, Justin Long. Surprisingly, she was also dating Fabrizio Moretti, the drummer from The Strokes. The last official one on this list is Will Kopelman, whom she married in 2011. They had two children, but they got divorced in 2016.

Warren Beatty

Warren Beatty

Warren Beatty found his first partner in the 1950s in actress Lee Grant, yet it was short-lived. He was dating several prominent figures like Stacey Nelkin, Isabel Ajdani, and Madonna. He also dated a supermodel Elle Macpherson and Janice Dickinson. Warren Beatty was romantically linked to a British actress, Charlotte Lewis in 1990. He married only once to Annette Bening in 1991, whom he met while filming Bugsy. This was his last relationship, and they had four kids together.

Britney Spears

Britney Spears

The third one on this list is quite famous. You might be aware of this. It is Britney Spears with several relationships in her past. Her first boyfriend was Justin Timberlake, who lasted for 3 years. Then she went on to Wade Robson.

She was also dating Jason Alexander. Fast-forward to 2004, she married her fellow dancer, Kevin Federline. They had two beautiful children. Another famous relationship of Britney Spears is with Jason Trawick, and it lasted till 2013. After this, she was connected to David Lucado and Charlie Ebersol. Since 2016, Britney has been dating Sam Asghari but it ended in 2023.

Sienna Miller

Sienna Miller

Here is another celebrity with the most relationships. Her first one was Jude Law with whom she started dating in 2004. After 2 years, they split up. They gave another chance in 2009 but it did not work out. she moved on to Daniel Craig. She has been associated with many actors and popular figures including Balthazar Getty, Rhys Ifans, and Tom Sturridge. She was dating Lucas Zwirner in 2018, but this was confirmed in 2020. They called off their engagement in the same year. Anyways, currently, she is dating Oli Green. This started in 2022. They were seen with their daughter in January 2024.

Halle Berry

Halle Berry

Halle Berry was dating a singer, Van Hunt. After some years, she dated Alex da Kid, a well-known singer. A controversy concerning Halle says that she left Spike Lee for her co-star in the movie Jungle Fever, Wesley Snipes. She had many other relationships and got hitched to Eric Bennet in 1999. They divorced in 2005.

Some of the popular names who were connected to Halle are Michael Ealy, Heavy D, Terrence Howard, and Gabriel Aubry. Gabriel Aubry was a Canadian model, who had a daughter with Halle. In the present, Halle is dating Alexander Grant.

Jennifer Aniston

Jennifer Aniston

When Jennifer started dating Charlie Schlatter in 1990, it came out as huge news. She got connected to Daniel McDonald and Adam Duritz before 1995. After this time, she was in a relationship with a director, Tate Donovan. Later, she found Paul Rudd.

Jennifer got married to Brad Pitt in 2000, but they got separated after 5 years. She gave the reason that Brad Pitt was wasting his life. She was associated with actor Vince Vaughn whom she met while she was filming The Break-Up in Chicago. Her most recent relationship was with Wanderlust co-star, Justin Theroux, with whom she separated in 2018.

Jennifer Lopez

Jennifer Lopez

Most of you might be familiar with the love stories of Jennifer Lopez. Her first boyfriend was Ojani Noa, a waiter whom she met in a Cuban restaurant. She went on to a star, Diddy Combs but they split up in 2001.

She was married to Chris Judd for two years before she started dating Marc Anthony. The two got engaged but never got married. Later, she had two kids from Marc Anthony. They both were married for around 6 years. Jennifer Lopez also dated Casper Smart, Drake, and Hall of Famer level baseball player Alex Rodriguez. Further, she got married to Ben Affleck in 2022.

Rihanna

Rihanna

Rihanna got her first boyfriend, Chris brown. They met when they were quite young in 2005. The list of Rihanna’s relationships is quite long. You can see the names Karim Benzema, Matt Kemp, and Ryan Phillippe. It still goes on, but it’s a bit difficult to mention all of them here. In 2016, she was dating Leonardo DiCaprio, after being with Travis Scott for a while Drake and Rihanna were also connected on and off until 2016 when they officially got together. Yet, netizens were surprised when Rihanna was seen kissing Hassan Jameel, a Saudi billionaire. Later, She has found her man, A$AP Rocky and they had a child.

Leonardo Di Caprio

Leonardo Di Caprio

His first romantic relationship was with a Brazilian model, Gisele Bundchen in 2002. He continued an on-and-off relationship with an Israeli model, Bar Rafaeli. A few famous female celebrities he was dating were Blake Lively, Erin Heatherton, Toni Garn, and Kelly Rohrbach. He also dated a Danish model, Nina Agdal. Rumors rose about Leonardo’s relationship with Lorena Rae, but it was never confirmed. Apart from this, he had numerous relationships that we cannot even count.

Sandra Bullock

Sandra Bullock

Going back to 1992, Sandra was dating Tate Donovan, whom she met on the set of Love Potion. She had a brief connection with Troy Aikman. She moved on to Don Padilla in 1996. After her relationship with McConaughey ended, she moved towards musician Bob Schneider, a musician.

She also dated Ryan Gosling. Some other men from this long list are Bryan Randall, Jesse James, Ryan Reynolds, and Chris Evans. She is continuing with Bryan Randall.

Taylor Swift

Taylor Swift

You might have expected her on this list. The famous singer Taylor Swift started dating Joe Jonas in 2008. She is famous for writing songs about her exes. He dedicated “last kiss’, “forever and always” to Joe after their breakup. In 2009, she started dating model, Lucas Till. The list of relationships of Taylor includes the names Taylor Lautner, the Twilight Hero, John Mayer, Cory Monteith, and Jake Gyllenhaal. She was committed to Harry Styles in 2013. She wrote the songs, “I knew you were in trouble”, and “Out of the Woods” for Harry style. Her longest working relationship was with Calvin Harris, though it only lasted a year.

Scarlett Johansson

Scarlett Johansson

Scarlet Johansson said in an interview that staying committed to one person is not natural. This aligns well with her personality. She has been linked to many men, and the first one on the list is  Jack Antonoff, a singer. She dated Jared Letto and later switched to Derek Jeter. Some other boyfriends of Scarlett as Sean Penn, Justin Timberlake, and Dauriac. She got hitched to Ryan Reynolds but got divorced because of the clashing personality of the couple. The last one we can see now is Colin Jost. They also welcomed a child.

Kate Hudson

Kate Hudson

Kate Hudson started her love life with Chris Robinson in 1998 who was a popular musician from the band, the Black Crowes. She has a kid from Chris. Kate dated Owen Wilson, but they took a break for some time. In this break, she found herself dating Dax Shepherd, and the break never ended. She hung out with Matthew Bellamy and Heath Ledger. A good part of her love life was a cyclist, Lance Armstrong. She was dating New York player, Alex Rodriguez, and golfer, Adam Scott. Her relationship with Nick Jonas continued off and on. Currently, she is seeing Danny Fujikawa.

Amanda Seyfried

Amanda Seyfried

The first hero of Amanda’s love life was Micah Alberti, whom she found in 2002 on the set of All My Children. While she was on break with Micah, she was dating Emile Hirsch. She got linked to Jesse Merchant and this was destroyed after her relationship with the Mamma Mia hero, Dominic Cooper. From 2008 to 2015, she got connected with Alexander Skarsgård, Ryan Philippe, and Andrew Joblen. Josh Hartnett and Desmond Harrington. She is enjoying her love life with the actor Thomas Sadoski from 2016.

Natalie Portman

Natalie Portman

Jake Gyllenhaal was her first boyfriend, whom she found in 2002. After the shooting of Star Wars, she started dating Gael Garcia, a well-known actor and producer. She took a break that never ended. During this break, she was linked to DJ Moby. She was also connected to Nathan Bogle and Devendra Banhart. She is now co-parenting her child with Benjamin Mille Pied.

Kaley Cuoco

Keley CUoco

Kaley Cuoco got famous because of her role in The Big Bang Theory. She has been in many relationships till today. She was dating Johnny Galecki for two years, but for some reason, she kept it private. Their breakup followed her connection with Mayim Bialik. Kaley was also connected to Josh Resnik, Christopher French, and Bret Bollinger. She split up with Bret in January 2013. She continued with Ryan Sweeting and Paul Balckthorne. She is currently dating the popular actor Tom Pelphrey, after her breakup with Karl Cook.

Charlie Sheen

Charlie Sheen

When we are talking about celebrities with the most number of relationships, how can we forget Charlie Sheen? This popular stat from Two and a Half Men and Platoon had enjoyed many girlfriends in his life. He started his love life alongside Capri Anderson but was seen dating a real estate investor, Brooke Bueller in 2006. He also married Denise Richards and Donna Peele but all these three marriages ended up in early divorces. He has been linked to many other Hollywood stars showing his controversial lifestyle.

John Mayer

John Mayer

John is a renowned singer and songwriter. He had the privilege to date many high-profile celebrities. He first got attention for his relationship with Jennifer Love Hewitt. Later, he started seeing Jessica Simpson, who is another star on this list. Jennifer Aniston and Taylor Swift are among the many other girls John Mayer was found to be dating. People often call him a playboy because his relationships are always on the media.

Colin Farell

Colin Farell

Famous for his characters in Phone Booth, and In Bruges, Colin had several girlfriends. She started with Amelia Warner. Later, he was found dating Kim Bordenave, Britney Spears, and Angelina Jolie. Colin’s love life was as adventurous as his acting career. Lindsay Lohan was another girlfriend of Colin Farrell. He was also connected to Kelly McNamara in 2016.

Jude law

Jude law

Jude Law, the famous actor of Sherlock Holmes, has had over 11 relationships. His first one was with the actress Sadie Frost. They got married soon and had 3 children together, but it ended up in separation. After this, he started seeing Pearl Love, with whom he had a daughter. Other actors Jude has been linked to are Cameron Diaz, Samantha Burke, and Lindsay Lohan.

George Clooney

George Clooney

For those who don’t know, George Clooney is an Academy Award-winning actor known for Oceans Eleven and Syruana. His life gave him many romantic relationships. He first gained focus on his marriage to Talia Balsam. He was also dating Kelly Preston before this. After his divorce, from Talia, he dated many popular stars including Renée Zellweger, Krista Allen, and Stacy Keibler. George finally found his last love in the lawyer Amal Alamuddin, and they got married in 2014.

Tom Cruise

Tom Cruise

Tom Cruise, one of Hollywood’s biggest stars with films like Top Gun and Mission: Impossible, has had over 10 relationships. He first connected to Heather Locklear, then Rebecca De Mornay. He tied the knot with Mimi Rogers in 1987. Later he met Nicole, and he adopted two children. After their divorce, he married Katie Holmes. They had a daughter. Tom has also been associated with Hayley Atwell and Elsina Khyarova

Ben Affleck

Ben Affleck

Ben Affleck is an actor and filmmaker known for Argo and Batman v Superman. He first dated actress Gwyneth Paltrow somewhere in the late 1990s. He then had a highly publicized relationship with Jennifer Lopez. Yet this was followed by a marriage to Jennifer Garner. They have three children. Ben has also been linked to Lindsay Shookus and Ana de Armas. Recently, he tied the knot with Jennifer Lopez.

Sean Penn

Sean Penn

Sean Penn is another Academy Award-winning actor. He is known for Mystic River and Milk. He first married pop icon Madonna, who was his farm’s popular relationship, and later married actress Robin Wright, with whom he has two children. Sean has also dated several other celebrities. Among this list, the popular names are Leila George and Charlize Theron.

Mila Kunis

Mila Kunis

Mila Kunis is widely known for her role in That ’70s Show. She first entered the spotlight with her long-term relationship with Macaulay Culkin. They were together for eight years before parting ways. She then started dating her former co-star Ashton Kutcher in 2012. The couple finally got married in 2015. They have since welcomed two children, Wyatt and Dimitri, into their family.

Demi Moore

Kirsten Dunst

The iconic actress from Ghost and G.I. Jane, Demi Moore has a loving romance history. Her first connection was with Freddy Moore. As you can see, she adopted his last name. Later, she married actor Bruce Willis. They had three daughters: Rumer, Scout, and Tallulah. After her divorce from Willis, she married Ashton Kutcher. They ignored their huge age difference. Their relationship got much popularity, but they eventually divorced in 2013.

Kirsten Dunst

Demi Moore

Kirsten Dunst got into the limelight because of her role in Spider-Man. She began dating actor Jake Hoffman in 1998. Their relationship lasted for about two years. She was also linked with Ben Foster, Jake Gyllenhaal, and Garrett Hedlund, her co-star in On the Road. Kirsten is currently married to Jesse Plemons, her co-star from Fargo. The couple has two children together, and they are working on various projects.

Cameron Diaz

Jessica Simpson

The star of The Mask and There’s Something About Mary can never be forgotten. She dated Carlos de la Torre in 1990 and was later in a relationship with Jared Leto. Cameron also had a long-term relationship with Justin Timberlake. Rumors were seen about the relationship of Elon Musk with Cameron Diaz.  In 2015, she married Benji Madden, a guitarist from Good Charlotte. The couple welcomed their daughter, Raddix, in 2019.

Jessica Simpson

Cameron Diaz

Singer and actress Jessica Simpson has been involved in 11 relationships. She first got into the limelight because of her marriage with Nick Lachey. They got famous for their reality TV show. She divorced him in 2006. Later, she was seen dating John Mayer. Soon after her breakup with John, she got connected to Tony Romo. Others form this list are Billy Corgan, Jeremy Renner, and and Eric Johnson. Jessica’s love life has always been in the spotlight.

Winona Ryder

Winona Ryder

Winona Ryder has had a series of popular relationships. She dated Rob Lowe at the start of her love life. Her relationship with Johnny Depp famously intense, even resulting in Depp’s “Winona Forever” tattoo. She was also linked with David Pirner. Currently, Winona is in a long-term relationship with fashion designer Scott Mackinlay Hahn. They have been together since 2011.

Matthew McConaughey

Matthew McConaughey

Matthew McConaughey is an Oscar-winning actor from Dallas Buyers Club. Fans can never forget his love life. He dated Sandra Bullock after they met on the set of A Time to Kill. He also had a relationship with Cassandra Hepburn, an actress. Matthew eventually found lasting love with model Camila Alves. The couple married in 2012 and have three children: Levi, Vida, and Livingston. He was also seeing Ashley Judd his costar from The Locusts.

Elliot Page

Elliot Page

Elliot Page was in the limelight because of his roles in Juno and Inception. She got many romantic relationships into his life, beginning with Ben Foster in 2006. Following this, he was linked with actors and filmmakers like Samantha Thomas and Emma Portner. He married Emma in 2018. Yet, they got separated in 2021. Elliot is usually a private person, who keeps his relationships away from the limelight. He has only made a few public appearances with some of his partners.

Amber Heard

Amber Heard

Amber is a famous actress from Aquaman and The Rum Diary. She is also another actress with 10 relationships, starting with the popular photographer Tasya van Ree. This continued from 2008 to 2021. Later, she got hitched to Johnny Depp in 2015. Johnny Dep is also popular for numerous relationships and breakups. This ended suddenly, as expected, in 2017. After this time, she was linked with Elon Musk and Bianca Butti. The list continues.

Bradley Cooper

Bradley Cooper

The popular star of A Star Is Born is Bradley Cooper. She has been associated with many men till yet. His first high-profile relationship was with actress Jennifer Esposito. They only got married for a brief time. He has also dated Renée Zellweger, Zoe Saldaña, and Suki Waterhouse. Bradley’s another relationship was with model Irina Shayk. They were blessed with a beautiful daughter. His current girlfriend is reported to be Gigi hadid, the superstar.

Ryan Reynolds

Ryan Reynolds

The Deadpool and The Proposal actor Ryan Reynolds has had numerous relationships. He did have many relationships before it, but he first gained attention with his engagement to singer Alanis Morissette. He then married Scarlett Johansson, yet they divorced soon. Ryan is currently married to actress Blake Lively, and they have three children.

Jake Gyllenhaal

Jake Gyllenhaal

Jake Gyllenhaal has dated several popular actresses and filmmakers. He was in a relationship with Jenny Lewis in 2001. This couple drew much media attention. Their relationship lasted for a while. Later, Jake dated Kirsten Dunst. This relationship was more private, but they were often seen together until their split. Jake was also linked with Taylor Swift, and their brief but intense relationship was behind several of her songs. He has also been romantically connected with actresses Natalie Portman and Minka Kelly. Currently, Jake is dating French model Jeanne Cadieu.

Ashton Kutcher

Ashton Kutcher

The Two and a Half Men star had 8 relationships. Early in his career, he dated Monet Mazur. He was also in a relationship with January Jones. Ashton’s marriage to Demi Moore was well-liked by the fans. It received praise due to their 15-year age difference. Their relationship had many public appearances and collective projects. Yet, they ended in divorce. Ashton later reconnected with Mila Kunis. They started dating in 2012, got engaged in 2014, and married in 2015. The couple now has two children. You can see glimpses of their life on social media.

Chris Evans

Orlando Bloom

Chris Evans’s first relationship was with Jessica Biel. It lasted for several years. They were considered one of Hollywood’s golden couples. Chris was also dating Minka Kelly on and off over the years. Each time they were seen together, they were appreciated. More recently, he was in a relationship with comedian Jenny Slate. He met her while filming Gifted. Their relationship ultimately ended. Now, Chris is dating Portuguese actress Alba Baptista. They have been seen together frequently.

Orlando Bloom

Chris Evans

The famous star of Pirates of the Caribbean and The Lord of the Rings found his first love in Kate Bosworth. They were together for several years before parting ways. Orlando then married supermodel Miranda Kerr in 2010. They have a cute son named Flynn. Their marriage continued until 2013. They are co-parenting their son. After his divorce, Orlando was seeing Selena Gomez. He got engaged to singer Katy Perry. The couple welcomed their daughter, Daisy Dove, in 2020. They have been open about their relationship and family life.

Eva Longoria

Eva Longoria

Eva Longoria had many relationships, but only some of them were caught in the public eye. She was dating Ernesto Arguello in 2013. She also married basketball star Tony Parker. Their marriage ended in 2011 after rumors of infidelity. Eva then dated and married businessman José Antonio Bastón in 2016. The couple had a son, Santiago, in 2018. Eva’s love life saw many ups and downs, but she has found her happiness with Baston. They frequently share their family life on social media.

Were you surprised with this list of celebrities with the highest number of relationships? Our spotlight never dims, and the cameras never stop flashing. Many of these relationships turned into marriages, but some broke before it. These love stories may continue on and off. Let’s wait before we get another official announcement of a marriage or a date!

Rahis Saifi
Rahis Saifi
Rahis Saifi always remain passionate towards gaming and innovation. He is currently playing GTA V and coming out with gameplay tricks.

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