40+ Celebrities With Most Affairs

In the glitzy and glam world of Hollywood, attraction and relationships are bound to happen. Like everyone else, celebrities also experience the complexities of love and have found themselves embroiled in some high-profile affairs that have captivated the attention of the public. So, here are 45 well-known celebrities who had affairs during their time in Hollywood!

Marilyn Monroe and John F. Kennedy

Marilyn Monroe and John F. Kennedy

The relationship between Marilyn and John is one of the most high-profile affairs of its time. Rumours about the couple started to spread when Marilyn gave a steaming performance in front of Kenndy. At the time, it was also rumoured that the American musician was dating numerous men, including Attorney General Robert F. Kennedy, John’s brother.

Barbara Hershey And Sayid

Barbara Hershey And Sayid

The American actress from Lost started dating Sayid in late 1998 and to everyone’s surprise, it was revealed that the couple had a twenty-one-year age gap. However, initially, it did not affect the couple’s relationship but in 2010 the couple decided to go their separate ways. Since then both the actors have been linked to several celebrities.

David Beckham And Rebecca Loos

David Beckham And Rebecca Loos

After marrying Victoria Beckham, the former English footballer was linked to his personal assistant, Rebecca Loos in the year 2004. The PA stated to news outlets that she is indirectly the second wife because David had sexual relations with her. In response to this, the former footballer said that he is happily married and has a very loving wife along with two children.

Jack Nicholson And Lara Flynn Boyle

Jack Nicholson And Lara Flynn Boyle

In 1999, the American actor and filmmaker started dating Lara Flynn Boyle. She said to several news outlets that dating Jack Nicholson is like having a relationship with a king. In addition to Lara, the filmmaker has also dated Michelle Phillips, Anjelica Huston, and Rebecca Broussard after his divorce from the Terror co-star Sandra Knight.

Nicolas Cage And Brooke Shields

Nicolas Cage And Brooke Shields

The well-known film producer, Nicolas Cage has dated many people in the past but his most popular affair has been with Brooke Shields. The couple started dating in the 1980s and were spotted together at the premiere of Moonstruck. However, now they have been married to different people with Nicolas Cage being married to Alice Kim and Brooke Shields being married to Chris Henchy.

Elizabeth Taylor And Eddie Fisher

Elizabeth Taylor And Eddie Fisher

In the 1950s, the affair between Eddie Fisher and Elizabeth Taylor caught everyone’s attention because Fisher married Taylor in 1959 when her husband Mike Todd died. However, after just five years together, Elizabeth Taylor filed a divorce petition and tied the knot in 1964 with Richard Burton who was her co-star in Cleopatra.

Natalie Portman And Moby

Natalie Portman And Moby

During her teenage years, Natalie Portman was linked to the American musician and songwriter. In his 2019 memoir, Moby stated that Natalie and he went on pretty dates together and were together for just a while because, at that time, she just graduated high school. After breaking up, Natalie has been in a relationship with Devendra Banhart and married Benjamin Millepied. But the couple has also ended their decade-long marriage after finalizing a divorce in March 2024.

Brad Pitt And Angelina Jolie

Brad Pitt And Angelina Jolie

On the set of Mr. & Mrs. Smith, Brad Pitt and Angelina Jolie sparked a romance and started dating. In 2005, this led to Jennifer Aniston filing for divorce from her husband Brad Pitt. After getting separated from Aniston, the actor married her co-star but ultimately got divorced from her in 2016 after 10 years. Since then, Brad Pitt has been linked to several women in Hollywood.

Billy Bob Thornton And Angelina Jolie

Billy Bob Thornton And Angelina Jolie

Billy Bob started his affair with Angelina Jolie when his wife, Laura Dern was away from their home for work. The couple was married for two years but after Angelina’s interference, things between them ended abruptly in the 1990s. In an interview with ABC News, Laura Dern explained her separation from Billy Bob Thornton and stated that she never heard back from him after he got married to Angelina Jolie.

Anne Heche And Steve Martin

Anne Heche And Steve Martin

On the set of the film A Simple Twist Of Fate, Anne Heche and Steve Martin met each other and quickly fell in love. They dated for two years and were spotted at multiple events holding hands including movie premieres and award shows. However, now the couple is separated and has been linked to many celebrities such as Ellen DeGeneres, Coleman “Coley” Laffoon, and James Tupper.

Humphrey Bogart And Lauren Bacall

Humphrey Bogart And Lauren Bacall

During the filming of To Have and Have Not in 1944, the two actors met each other and started dating. At that time, the couple had a 25-year-age difference and Humphrey Bogart was married. But Bogart divorced her wife and got married to Bacall in 1945 in addition to having two children together.

Courtney Love And Edward Norton

Courtney Love And Edward Norton

In 1996, the American guitarist was in a relationship with his The People Vs. Larry Flynt co-star Edward Norton. However, due to her two-decade-long meltdown, the couple got separated. Since then, Courtney has been linked to several men, including Steve Coogan, Billy Corgan, Julian Casablancas, and Jim Barber.

Hugh Grant And Elizabeth Hurley

Hugh Grant And Elizabeth Hurley

In 1995, the English actor started dating Elizabeth Hurley and their relationship became the most-headlined affair when Grant was caught with a prostitute named Divine Brown. The actor also paid a huge fine for his inappropriate behavior in a public place. Ultimately in 2000, the couple got separated. Since then, Hugh Grant has dated Tinglan Hong, Jemima Khan, and Anna Eberstein.

Frank Sinatra And Ava Gardner

Frank Sinatra And Ava Gardner

While being married to Nancy, Frank Sinatra started a romantic affair with Ava Gardner. However, in 1951, the American singer divorced his wife and got married to Ava. Furthermore, Sinatra was also involved with many women while he was married to Gardner. This ultimately led to their divorce in the year 1957, proving that some men cannot be trusted.

Ryan Gosling And Sandra Bullock

Ryan Gosling And Sandra Bullock

The Canadian actor started dating Sandra Bullock in the year 2002 while filming Murder By Numbers. At that time, the couple had a 16-year age difference which was mocked by many Hollywood celebrities. However, the couple got separated and since then Ryan has dated many women including Rachel McAdams, Kat Dennings, Blake Lively, Olivia Wilde, and Eva Mendes.

Jude Law And Sienna Miller

Jude Law And Sienna Miller

The Holiday actor, Jude Law, got involved in an affair with his children’s nanny, Daisy Wright, while he was engaged to his fiancée Sienna Miller. The couple broke up after Jude’s public apology, and since then, he has been with Phillipa Coan, Rachel Bourlier, Catherine Harding, Alicia Rountree, and many more.

Cameron Diaz And Robbie Williams

Cameron Diaz And Robbie Williams

Before getting married to Benji Madden in 2015, Cameron Diaz dated several men, including Robbie Williams. The couple’s affair was the most talked-about relationship in the past. They started dating in 2005 and were spotted together at several locations, including a beach. After getting separated from him, Cameron was seen spending time with P. Diddy, but they never confirmed their affair to the media.

Cary Grant And Sophia Loren

Cary Grant And Sophia Loren

After getting married to actress Betsy Drake, the Hollywood heartthrob had an affair with Sophia Loren while they were filming Houseboat. However, it was pointed out that the couple had a 30-year age difference, and after some time, Sophia Loren dumped Cary Grant and got married to Italian actor Carlo Ponti.

Jessica Simpson And Billy Corgan

Jessica Simpson And Billy Corgan

The well-known American singer has had several affairs but the most talked about affair of her is with Billy Corgan. The couple dated for a while in 2009 and got separated after just one year in 2010. Since then she has been in romantic relationships with Nick Lachey, Jensen Ackles, Adam Levine, Bam Margera, John Mayer, and Tony Romo.

Tom Cruise And Sofia Vergara

Tom Cruise And Sofia Vergara

The Hollywood icon has had several high-profile relationships in the past. He has married three women in the past, including Mimi Rogers (1987 to 1990), Nicole Kidman (1990 to 2001), and Katie Holmes (2006 to 2012). However, after getting separated, he romanced several actresses such as Sofia Vergara, Cher, Heather Locklear, Melissa Gilbert, Rebecca De Mornay, and Penélope Cruz.

Jesse James And Sandra Bullock

Jesse James And Sandra Bullock

While being married to Sandra Bullock, the American entrepreneur had several affairs with many women. Michelle McGee, a dancer in the Hollywood industry, claimed that Jesse had an illicit relationship with him behind his wife’s back. Due to this, Sandra Bullock filed for divorce from him and it was finalized in 2010. Also, Jesse James issued a public apology to Sandra Bullock and his kids when he was accused of cheating by four more women.

Marlee Matlin And John Stamos

Marlee Matlin And John Stamos

The recipient of numerous awards has had several affairs in the past, but her relationship with John Stamos in 1989 caught everyone’s attention. But after a brief period of time, the couple got separated, and since then, Marlee has dated many men, including Kevin Grandalski, David E. Kelly, River Phoenix, Richard Dean Anderson, and Rob Lowe. Additionally, she has also dated William Hurt, who was her co-star on Children of a Lesser God.

Kristen Stewart And Robert Pattinson

Kristen Stewart And Robert Pattinson

The Twilight actress while filming for the hit franchise, started dating her co-star Robert Pattinson. But in 2012 she was caught cheating on him with Rupert Sanders who was her director on the film, Snow White and the Huntsman. Later she apologized to Robert in public and they started their affair again but got separated. Now, Kristen is happily engaged to Dylan Meyer.

Matt Damon And Winona Ryder

Matt Damon And Winona Ryder

After dating for two years in 1997, Matt Damon and Winona Ryder got separated in the year 2000. They met each other through a mutual friend named Gwyneth Paltrow. During their time together, they were known as the It Couple of Hollywood. Since then, Winona Ryder has been in relationships with Rob Lowe, Christian Salter, Johnny Depp, David Pirner, David Duchovny, and more.

David Letterman And Regina Lasko

David Letterman And Regina Lasko

The popular American television show host got married to his longtime girlfriend Regina Lasko in 2009. But after only six months, it came to notice that the host was involved in a sex scandal with multiple women and was also accused of cheating. He also had many affairs while his marriage was still subsisting with Regina Lasko.

Dolph Lundgren And Grace Jones

Dolph Lundgren And Grace Jones

The Swedish actor had an affair with Grace Jones in 1985 when they were filming A View to a Kill. The couple was known for their PDA and wild lifestyle. Sadly, after the film received bad critic reviews and did not do well on the silver screen the couple parted ways. After this, Dolph had romantic relationships with Emma Krokdal, Jenny Sandersson, Anette Qviberg, Paula Barbieri, Sam Phillips, and more.

Elin Nordegren And Tiger Woods

Elin Nordegren And Tiger Woods

While being married to Elin, Tiger Woods was having an affair with Rachel Uchitel, a nightclub manager. After it became public knowledge, Elin and Tiger had an altercation at a golf club and labeled it as a private matter to the media. After this, 12 more women came forward and accused Tiger of having affairs with them. Ultimately in 2010, the couple finalized their divorce in court.

Russell Brand And Ginger Spice

Russell Brand And Ginger Spice

The English comedian started dating Ginger Spice girl Geri Horner, during their time at the London Olympics together. But the relationship between the couple was never made official. After this, he has been in romantic relationships with Katy Perry, Isabella Brewster, Jemima Khan, Teresa Palmer, Nikolett Barabas, and many more.

Kim Kardashian And Kanye West

Kim Kardashian And Kanye West

Kim Kardashian, the high-profile American Socialite, has married three times including Damon Thomas for four years, Kanye West for eight years, and Kris Humphries for two years. The actress started dating Kanye West in 2012 and got married to him in 2014. But the couple got separated in 2021 and since then Kim has been linked to Odell Beckham Jr., Reggie Bush, Pete Davidson, and more.

Ted Danson And Whoopi Goldberg

Ted Danson And Whoopi Goldberg

While being married to his wife Casey Coates since the year 1993, the American actor also had a brief affair with Whoopi Goldberg. But their time together was very short and after divorcing Casey Coates, Ted was romantically involved with Mary Steenburgen and ultimately got married.

Matthew Perry And Lizzy Caplan

Matthew Perry And Lizzy Caplan

The Friends actor had several affairs in the past but his most talked about relationship was with Lizzy Caplan. The couple started dating in 2006 and were together for six years. This was the longest affair of Matthew during his lifetime. But after some time the couple broke up in 2012 and he was linked to Julia Roberts, Cameron Diaz, Gwyneth Paltrow, and Yasmine Bleeth.

Lance Bass And Danielle Fischel

Lance Bass And Danielle Fischel

In 1999, the romantic affair of Lance Bass and Danielle Fischel came to public knowledge. However, the couple broke up in the year 2000 after Bass issued a statement that he was gay. Since then, he has been married to Michael Tuchin whom he met in 2014.

Justin Timberlake And Fergie

Justin Timberlake And Fergie

The two actors started dating each other in the year 1997 when they were on the show Mickey Mouse Club and Kids together. However, it was revealed that the couple had got separated because Fergie was 6 years older than him. After this, Justin has been in the news for having affairs with Britney Spears, Cameron Diaz, Jessica Beil, Olivia Wilde, and Tatyana Ali.

Martha Plimpton And River Phoenix

Martha Plimpton And River Phoenix

While filming Running on Empty, the on-screen couple ignited an off-screen affair and started dating in 1986. The couple was together for almost three years and broke up in 1989. Apart from River, Martha also dated Fred Armisen from 2005 to 2006 and was also engaged to Jon Patrick Walker.

Johnny Depp And Amber Heard

Johnny Depp And Amber Heard

The Pirates of the Caribbean actor has had a very tumultuous personal life. He had romantic affairs with Winona Ryder, Lori Anne Allison, Vanessa Paradis, and Kate Moss before getting married to Amber Heard. However, his marriage to Amber resulted in a legal case that took three years to resolve. After this, Johnny Depp has recently been linked to Joelle Rich.

Rihanna And Chris Brown

Rihanna And Chris Brown

The popular singer started dating hitmaker Chris Brown in the year 2007. However, the couple parted ways in 2009 when she accused Chris of physically assaulting her. Since then, Rihanna has had affairs with Drake, Travis Scott, Matt Kemp, A$AP Rocky, and Hassan Jameel.

Gwen Stefani And Gavin Rossdale

Gwen Stefani And Gavin Rossdale

The American singer started dating the lead singer of the band Bush after meeting in 1995. The couple got married in 2002 before dating for several years. However, after a long time together, the two singers announced their divorce in 2015. After this, Gwen Stefani also had romantic affairs with Tony Kanal and Blake Shelton.

Kelly Preston And George Clooney

Kelly Preston And George Clooney

Before marrying John Travolta, Kelly Preston had affairs with numerous men including George Clooney. The couple started dating late 1980s but later parted ways. After this, the actress was linked to Kevin Gage whom she married in 1985, and was also engaged to  Charlie Sheen in 1990.

Zayn Malik And Gigi Hadid

Zayn Malik And Gigi Hadid

The former member of One Direction has had several high-profile affairs but his marriage with Gigi Hadid was the most talked about one. The two were dating on and off from the year 2015 to 2021 and also had a daughter named Khai. Apart from this Zayn also had affairs with Perrie Edwards, Selena Gomez, Geneva Lane, Rebecca Ferguson, Stephanie Davis, and many more.

Bruce Willis And Demi Moore

Bruce Willis And Demi Moore

The retired actor, who is now happily married to Emma Heming Willis for almost ten years has had a high-profile affair in the past. The actor was romantically involved with Demi Moore and the couple was called Hollywood’s golden couple. Bruce and Demi got married in 1987 after dating for only four months. However, the couple parted their ways in 2000.

Flava Flav And Brigitte Nielsen

Flava Flav And Brigitte Nielsen

The American Rapper started a romantic affair with Brigitte Nielsen in the year 2005 and this was labeled as the most surprising affair of all time. However, after a short period of time, the couple parted ways. Since then Flava has been linked to Latresha Bradford, Nicole Alexander, Maureen McPhilmy, and Chandra Davis.

Jay-Z And Rosario Dawson

Jay-Z And Rosario Dawson

The dating rumors of Rosario and Jay-Z started to spark in the year 2000 when they were spotted by news outlets together at several events. However, later that year it was revealed that they had stopped seeing each other. After this, Jay-Z also had affairs with Beyoncé, Blu Cantrell, Rihanna, Charli Baltimore and many more.

Scarlett Johansson And Benicio Del Toro

Scarlett Johansson And Benicio Del Toro

In 2004, Scarlett Johansson had a brief romance with Benicio Del Toro. It was revealed that the couple had an intimate moment during the Oscar Awards in the elevator, but Toro denied the rumors. Apart from this, Johansson has also dated Ryan Reynolds, Romain Dauriac, Leonardo DiCaprio, and Colin Jost.

Sarah Jessica Parker and Robert Downey Jr.

Sarah Jessica Parker and Robert Downey Jr.

From 1984 to 1991, Robert Downey Jr dated Parker and they stayed together for almost the whole 80s together. After this, the 59-year-old actress has also had affairs with Michael J. Fox, JFK Jr. and Nicolas Cage. She also married Matthew Broderick in the year 1997.

Naomi Campbell And Leonardo DiCaprio

Naomi Campbell And Leonardo DiCaprio

In 1995, after the Titanic movie was released, Leonardo DiCaprio had a brief affair with supermodel Naomi Campbell. However, they broke up and are still good friends to date. After this, the American actor has also dated Amber Valletta, Gisele Bündchen, Virginie LeDoyen, Blake Lively and Eva Herzigová.

Megha Chauhan
Megha Chauhan
Megha Chauhan is an accomplished content writer who holds a degree in Law. Her extensive expertise in research and writing has helped her excel in this field. Her expertise spans from engaging blog posts and in-depth articles. Passionate about storytelling, Megha continually hones her skills to stay ahead of trends, ensuring her content remains fresh and impactful.

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