40+ Celebs With Amazing Dating Histories, Ranked
Dating someone is hard enough as it is, and now people are tracking every moment of it. I want to get away from that. The spotlight on star relationships in the media can come from involved parties posting happy pictures to social media and getting hundreds of likes or magazines making ‘who’s dating who’ lists. Here are some celebrities whose dating lives have made headlines over the years.
Warren Beatty
Warren Beatty has made himself a name over the years- he’s been nominated 15 times for an Academy Awards and 18 times for a Golden Globe. He’s a bit of a heartbreaker too. He was married to Annette Bening from 1992-now but was famed for his many girlfriends before tying the knot with his now-wife. It’s nearly impossible to list all the people with whom he was romantically linked, including stars like Faye Dunaway and royalty like Princess Elizabeth of Yugoslavia.
Zsa Zsa Gabor
Zsa Zsa Gabor was a well-known actress. In addition, she has been married nine times throughout her life. In 1935, she married Burhan Asaf Belge. They separated in 1941, and she married Conrad Hilton in 1942, whom she married until 19947.
Zsa Zsa Gabor
She married George Sanders from 1949 to 1954 and Herbert Hutner from 1962 to 1966. She married in 1975, first to Jack Ryan and later to Michael O’Hara. She married Felipe de Alba in 1983 and then Frédéric Prinz von Anhalt (shown) in 1986 until her death in 2016.
Leonardo DiCaprio
Not one person has reached the level of fame as Leonardo DiCaprio. Since his early roles, paparazzi eyes have been on him. Throughout the years, this has included paparazzi and fans closely following the people he’s dated.
Leonardo DiCaprio
This list has too many prominent figures to list, but some celebrities include Demi Moore, Gisele Bündchen, Sienna Miller, and Blake Lively.
Burt Reynolds
Burt Reynolds was one of the biggest heartthrobs of his generation, so it’s no surprise that people kept a close watch on who he went out with.
Burt Reynolds
Throughout his life, Reynolds had several relationships with people, many of which were high profile. Some of them include Judy Carne and Loni Anderson, as well as Lorna Luft, Kim Basinger, Tammy Wynette, Sally Field, Doris Day, Faye Dunaway, and more!
Madonna
Madonna is the Queen of Pop, and we even know everything about her. From her tours to her scenes on-screen, she grabs our attention. Of course, fans have wanted to know who the Queen of Pop has been dating over the years.
Madonna
She’s been romantically linked with several notable celebrities. Still, some of the more famous people she dated include Sean Penn – to whom she was once married – Warren Beatty, Antonio Banderas, Lenny Kravitz, and Willem Dafoe.
George Clooney
George Clooney is another Hollywood star who finally found his one true love. He’s been married to Amal since 2014, after being married to Talia Balsam from 1989 through 1993.
George Clooney
Clooney has had romantic relationships with Stacy Keibler, Elisabetta Canalis, Sarah Larson, Monika Jakisic, Teri Hatcher, and Dedee Pfeiffer. He was rumored to have dated Mariella Frostrup and Renée Zellweger as well.
Elizabeth Taylor
Elizabeth Taylor has left a legacy like no other in Hollywood. Her first marriage was to Conrad Hilton, Jr. right after she turned 18 in 1950 — but it only lasted eight months. She was married eight times throughout her career and to 7 different people.
Elizabeth Taylor
Her next marriages were to Mike Todd, Eddie Fisher, Richard Burton, John Warner, and Larry Fortensky. Taylor initially married Richard Burton from 1964 to 1974 and again from 1975 to 1976.
Rue McClanahan
Rue McClanahan and her Golden Girls character, Blanche, had more in common than one would think. For example, they’ve both got some experience with dating! The star has had a few long-term relationships with Tom Bish, Norman Hartweg, Peter DeMaio, and Sam Fisher.
Rue McClanahan
Finally, she married Morrow Wilson. They separated legally in 2010 after being together for 12 years. She has even released this book titled “First Five Husbands… and the Ones Who Got Away.” This book also provides more information about her past in her romantic life.
Nicholas Cage
Nicholas Cage is one of the most recognizable actors in Hollywood. As for his dating record, we’ll look closely at his marriages. His first marriage to Patricia Arquette lasted from 1995-2001.
Nicholas Cage
He was married thrice in 2002 and 2004 to Lisa Marie Presley and Alice Kim, respectively, and in 2019 to Eric Koike. However, he annulled the marriage only five days after the wedding ceremony. He’s currently single and not yet engaged.
Sean Penn
From Fast Times at Ridgemont High to roles in movies like Milk and The Gunman, Sean Penn has garnered much attention over the years. He was with Elizabeth McGovern, Madonna, and Jewel Kilcher.
Sean Penn
Another decade found him with Robin Wright and Elle McPherson. Additionally, he’s been with Petra Nemcova, Natalie Portman, Jessica White, Charlize Theron, Valeria Golino, Scarlett Johansson, Garcelle Beauvais, Shannon Costello, Stacey Nelkin, Brigitte Nielsen, Peggy Trentini, and Calu Rivero.
Justin Timberlake
Justin Timberlake has been the subject of paparazzi attention for quite some time. All eyes were on NSYNC even before he made his solo debut. This has involved the globe paying close attention to Timberlake’s personal life.
Justin Timberlake
He dated Fergie, Jenna Dewan, Alyssa Milano, Staci Flood, Cameron Diaz, Scarlett Johansson, Jessica Biel, Olivia Munn, and Mila Kunis, among others.
Wilmer Valderrama
You probably think of Wilmer Valderrama when you think of your favorite sequences from That 70’s Show. Valderrama has created a name for himself in Hollywood outside of that role. This has encompassed both personal and business contacts over the years.
Wilmer Valderrama
Jennifer Love Hewitt, Majandra Delfino, Mandy Moore, Lindsay Lohan, Ashlee Simpson, Rihanna, Avril Lavigne, Demi Lovato, and Minka Kelly are among the celebrities he has dated. Valderrama is now engaged to Amanda Pacheco.
Kim Kardashian
Kim Kardashian is another star that attracts attention for her personal and business life. Plus, shows like Keeping Up With the Kardashians kept us updated.
Kim Kardashian
Before marrying Kanye West, Kim had relationships with Reggie Bush, Nick Lachey, Damon Thomas, Ray J, Nick Cannon, John Mayer, Gabriel Aubry, Kris Humphries, and Miles Austin. Kim has been in a public romance with Pete Davidson since her divorce from Kanye.
Paris Hilton
The socialite and reality star Paris Hilton has been open about her love life with us. Even more contemporary pieces, such as Paris in Love, demonstrate this. Her dating history has also featured a few well-known individuals.
Paris Hilton
Ryan Gosling, Criss Angel, John Mayer, Brody Jenner, Chad Michael Murray, Travis Barker, Benji Madden, Nick Carter, Adam Levine, Fredd Durst, and others expressed interest in her. Paris in love is the sequel to her engagement/wedding to Carter Reum.
Ryan Gosling
Ryan Gosling is one of Hollywood’s most well-known leading men. So it’s hardly surprising that his personal life has been extensively recorded. The celebrity has also worked with several other notable industry figures.
Ryan Gosling
Fans watched the romances of actresses such as Sandra Bullock, Famke Janssen, and Rachel McAdams in the early 2000s. He later dated Kate Dennings, Blake Lively, Casey LaBow, Olivia Wilde, and, most recently, Eva Mendes.
John Mayer
John Mayer is a well-known musician whose style has evolved significantly over the years. Many people, though, associate him with his early acoustic songs.
John Mayer
Fans rapidly got interested in the romantic elements of his personal life, not only his music, as they do with many singer-songwriters. We’ve seen him adorn magazine covers and party with celebrities like Jennifer Love Hewitt, Jessica Simpson, Taylor Swift (above), Katy Perry, Cameron Diaz, Rhona Mitra, and others.
Taylor Swift
Taylor Swift has dated various individuals, which is understandable given that she has spent much of her early adult life in the public glare. The actress has been in several high-profile partnerships throughout the years.
Taylor Swift
Harry Styles, Joe Jonas, Tom Hiddleston (above), Calvin Harris, Conor Kennedy, Taylor Lautner, John Mayer, and Jake Gyllenhaal are those involved. We’ve seen some of Swift’s thoughts on these relationships and how they were interpreted in many of her songs, as with many performers. She has been in a relationship with Joe Alwyn since 2016.
Derek Jeter
We’ve spent a lot of time looking at Hollywood celebrities, but let’s take a moment to examine Derek Jeter’s dating history.
Derek Jeter
Mariah Carey, Lara Dutta, Joy Enriquez, Jordana Brewster, Vanessa Minnillo, Jessica Alba, Adriana Lima, Jessica Biel, Minka Kelly, and Hannah Davis have all been spotted out and about with the pro athlete. Jeter and Davis married in 2016 and have three kids together!
Jennifer Lopez
Jennifer Lopez is a near-unstoppable Hollywood powerhouse. She appears to be involved in everything, from music to film. In real life, JLo has been in several romances that fans and paparazzi have closely tracked. This has featured both on-screen and off-screen relationships.
Jennifer Lopez
She joined Wesley Snipes, Sean Combs, Cris Judd, Marc Anthony, Casper Smart, Drake, and Alex Rodriguez on the red carpet. Still, her most famous romance is with Ben Affleck, since they were engaged back in the day before splitting up and reuniting years later!
Natalie Portman
Natalie Portman dated Lukas Haas in 1998, but the relationship didn’t endure. She began dating co-star Hayden Christensen after her stint in Star Wars.
Natalie Portman
Portman has also been associated with Andy Samberg, Jake Gyllenhaal, Nathaniel Philip Rothschild, Jude Law, Nathan Bogle, Devendra Banhart, and Rodrigo Santoro. Portman met her now-husband, Benjamin Millepied, on the set of Black Swan, and they are still married!
Drake
Drake is another celebrity that has captivated audiences for quite some time. His on-again, off-again romance with Rihanna was one of his most notable partnerships. It catches other people’s attention when musicians start dating.
Drake
Outside of this partnership, Drake has been in a few high-profile relationships and has even been the cause of various celebrity dating rumors, including allegations regarding Drake’s romance with Nicki Minaj.
Jennifer Aniston
Jennifer Aniston’s celebrity skyrocketed in the 1990s because of her portrayal as Rechel on Friends. She dated Daniel McDonald, Jon Stewart, Adam Duritz, Tate Donovan, and Paul Rudd during the 1990s.
Jennifer Aniston
Jennifer Aniston and Brad Pitt married at the turn of the century, but the couple divorced in 2005. Aniston re-entered the dating scene in 2006, this time with Vince Vaughn. Paul Sculfor, John Mayer, Harry Morton, and Justin Theroux followed him.
Orlando Bloom
Orlando Bloom has had a few high-profile partnerships with other great performers throughout the years. This includes his current relationship with singer Katy Perry.
Orlando Bloom
Sienna MiBloom and Perrin’s romance has captivated audiences in recent years. Kate Bosworth, Kirsten Dunst, Vanessa Minnillo, Penelope Cruz, and Naomi Harris have all dated the actor. Bloom began dating Miranda Kerr in 2008, and the couple was married from 2010 until 2015. Bloom an=”bottom-ad”]
Katy Perry
While we’re on the subject, let’s look at Kary Perry. Of course, as previously said, she is presently engaged to Orlando Bloom. She was dating Johnny Lewis of Sons of Anarchy fame at the outset of her career.
Katy Perry
In 2009, rumors began to circulate that Perry was romantically involved with Josh Groban, but this was never formally confirmed. Her second acknowledged romance was with Robert Ackroyd, followed by John Mayer (above), Diplo, and a few more reported flings.
Britney Spears
Britney Spears has been in the public glare for a long time. Like many other pop singers, Spears’ dating life received much attention during her career. In 1999, the actress dated Mario Lopez, who was later replaced by Robbie Carrico. Her relationship with Justin Timberlake lasted from 1999 until 2002.
Britney Spears
She’s dated Wade Robson, Fred Durst, Colin Farrell (shown), Columbus Short, Kevin Federline, Jonathan Rotem, Isaac Cohen, Howie Day, Adnan Ghalib, Jason Trawick, David Lucado, Charlie Eversol, and her most recent fiancee, Sam Asghari, since then.
Scott Baio
Scott Baio is well-known to fans for his appearances in classic comedies such as Charles in Charge and Happy Days. However, his personal life has also received considerable attention.
Scott Baio
While many aspects of his personal life have garnered notice, his dating history has been very public. The actor has been married to Renee Sloan since 2007. (pictured). Prior to it, he was involved in a number of high-profile partnerships. This includes dates with Denise Richards, Brooke Shields, and Liza Minnelli, among others.
Kaley Cuoco
Kaley Cuoco was dating producer and actor Thad Luckinbill in 2002. She then dated Kevin Zegers, Jaron Lowenstein, Josh Henderson, and finally Al Santos.
Kaley Cuoco
When Cuoco began dating Big Bang Theory co-star Johnny Galecki in 2008, fans rejoiced. It hardly lasted two years before they decided they preferred to be friends. Since then, Cuoco has dated Christopher French, Josh Resnik, Bret Bollinger, Henry Cavill, and others. Sweeting, Ryan She was also married for three years, till 2021, to Karl Cook.
Cameron Diaz
Cameron Diaz’s romantic life has always been a topic of speculation in her professional life. Fans kept a tight eye on her love life before she married Benji Madden and eventually withdrew from acting.
Cameron Diaz
Diaz has been linked to Criss Angel, Gerard Butler, Carlos De La Torre, Matt Dillon (pictured), Jared Leto, Justin Timberlake, Paul Sculfor, and Alex Rodriguez, among others. According to the rumor mill, she was also alleged to have had less recognized romances with Bradley Cooper and Robbie Williams.
Kate Hudson
Throughout her career, Kate Hudson has been associated with a number of noteworthy names. She appeared in Almost Famous as well as How to Lose a Guy in 10 Days. This charming celebrity has walked the red carpet with a number of renowned people throughout the years.
Kate Hudson
This has included romances with Matthew Bellamy, Alex Rodriguez, Adam Scott, Lance Armstrong, Heath Ledger, Justin Timberlake, Dax Shepard, Owen Wilson, and Shannon Leto, as well as a seven-year marriage to Chris Robinson.
Jennifer Love Hewitt
Jennifer Love Hewitt is a well-known actress in films such as The Ghost Whisperer. Hewitt is now married to Brian Hallisay and has been since 2013. Previously, reporters and interviewers were more than willing to follow Hewitt’s dating life.
Jennifer Love Hewitt
She has dated Ross McCall, Will Estes, Jowy Lawrence, Carson Daly, John Mayer, Wilmer Valderrama, Fred Savage, and John Cusack, to mention a few of her high-profile romances.
Charlize Theron
Throughout her career, Charlize Theron has astounded audiences. She’s ready to take the lead in anything from action to serious parts. Between 1995 and 1997, Theron was with Craig Phillip Bierko and then with Stephan Jenkins from 1998 to 2001.
Charlize Theron
Despite this, she was still romantically involved with George Clooney in 2000. She was married to Stuart Townsend (above) from 2001 until 2010 and subsequently to Keanu Reeves. Following a few more speculations, she quickly dated Alexander Skarsgard and Eric Stonestreet.
Sandra Bullock
Sandra Bullock was first photographed dating Michael Mailer in 1989. Bullock dated Love Potion No. 9 co-star Tate Donovan between 1992 and 1995. She then dated Troy Aikman and Matthew McConaughey, and there were rumors that she was dating Keanu Reeves.
Sandra Bullock
Following her breakup with McConaughey, the actress dated Dweezil Zappa, Bob Schneider, Hugh Grant, and Ryan Gosling and eventually married Jesse James. She dated Ryan Reynolds, Chris Evans, and then Bryan Randall after they separated.
Kirsten Dunst
Kirsten Dunst has spent much of her life working professionally. From Interview with the Vampire to Bring it On and beyond, Dunst has amassed a devoted following.
Kirsten Dunst
Of course, Dunst has a life outside of work, but as a celebrity, her personal life is frequently covered on magazine covers. This has included partnerships with celebrities such as Ryan Gosling, Jake Gyllenhaal, Tobey Maguire, Adam Brody, and Garret Hedlund, to mention a few.
Hayden Panettiere
Hayden Panettiere has done everything, from acting to singing to playing one of the main characters in the video game Until Dawn.
Hayden Panettiere
She has dated Stephen Colletti from Laguna Beach, Evan Ross, Milo Ventimiglia, Jesse McCartney, Steve Jones, Harry Morton, Kevin Connolly, Wladimir Klitschko, Scotty McKnight, and Brian Hickerson. Her marriage to Hickerson ended in 2020.
Scarlett Johansson
Scarlett Johansson hasn’t been seen with anybody other than her now-husband, Colin Jost. She does, however, have a star-studded dating past.
Scarlett Johansson
Relationships with Jude Law, James Holzer, Benicio del Toro, Patrick Wilson, Jared Leto, Josh Hartnett, Justin Timberlake, Ryan Reynolds, Sean Penn, Nate Naylor, and Roman Dauriac are among those mentioned. Johansson married Jost in a small wedding in 2020, and the actress and SNL actor had been dating since 2017, but they first met in 2006.
Jessica Simpson
Jessica Simpson was originally linked to Jensen Ackles, who would become famous for his role on Supernatural in 1998. Following that, she dated 98 Degrees band member Nick Lackey. They even married and lived together from 1999 to 2006.
Jessica Simpson
In 2004, Adam Levine, Fred Durst, Bam Margera, Dana Cook, John Mayer, Marcus Schenkenberg, Tony Romo, Billy Corgan, and her now-husband Eric Johnson were all rumored to be romantically involved with Simpson.
Amanda Seyfried
After the film’s release, Amanda Seyfried began dating All My Children co-star Micah Alberti. Partnerships followed this with Emile Hirsch, Jesse Marchant, and Dominic Cooper (all of whom are featured).
Amanda Seyfried
Cooper revealed in 2008 that she had a relationship with Alexander Skarsgard. It was during her connection with Mamma Mia! Following her divorce from Cooper in 2010, Seyfried dated Ryan Phillippe, Andrew Joblon, Josh Harnett, Desmond Harrington, Justin Long, and Thomas Sadoski, with whom she eloped.
Sienna Miller
We’ve mentioned Sienna Miller a few times, so it’s worth revisiting her time in the limelight. Her most well-known relationship was with Orlando Bloom in the early 2000s.
Sienna Miller
Following her split from Bloom, she dated or was reported to have dated Jude Law, Jamie Dornan, Daniel Craig, Taylor Christensen, Josh Hartnett, P. Diddy, Jamie Burke, James Franco, Rhys Ifans, Balthazar Getty, Tom Sturridge, Bennet Miller. There were even rumors of a more recent relationship with Brad Pitt.
Halle Berry
As the 1980s came to a conclusion, Halle Berry dated Kevin Costner and Danny Wood in that order. Berry was dating Spike Lee as the 1990s began.
Halle Berry
Berry left L
ee for Wesley Snipes after appearing in Jungle Fever with him. Speculations followed this seeing Eddie Murphy and subsequently marrying David Justice. Shemar Moore, Eric Benet, Fred Durst, Michael Ealy, Heavy D, Terrence Howard, Gabriel Aubry, Oliver Martinez, and, most recently, Alexander Grant have all dated her since they divorced in 1997.
Richard Pryor
Richard Pryor, the comedian, was married seven times. He, like Elizabeth Taylor, remarried several times rather than marrying seven separate women. His first marriage was to Patricia Price in 1961.
Richard Pryor
Shelley Bonis in 1967, Deborah McGuire in 1977, Jennifer Lee (shown) in 1981, Flynn Belaine in 1986, remarrying Belaine in 1990 following their divorce in 1987, and Jennifer Lee in 2001. They remained together till he died four years later.
Billy Bob Thornton
Billy Bob Thornton’s marriage to Angelina Jolie (pictured) from 2000 to 2003 is possibly his most well-known dating history. Thornton was married to Melissa Lee Gatlin from 1978 to 1980, and then to Toni Lawrence from 1986 until their divorce in 1988.
Billy Bob Thornton
He married Angelina Jolie in 1990 after a two-year marriage. He dated Connie Angland for 14 years after their divorce until they married in 2014.
Pamela Anderson
Pamela Anderson’s role in Baywatch established her as an iconic pop culture figure. Many people became interested in her personal life as well as her filmography as a result of this. Her first marriage was to Tommy Lee in 1995, only days after they met.
Pamela Anderson
Anderson married Kid Rock for a few months in 2006, years after they split. She’d married Rick Salomon for six months that year. The couple wedded for a few months in 2014, and the actress then had short-lived marriages with Jon Peters and Dan Hayhurst, her bodyguard.
Gary Oldman
Gary Oldman hasn’t had as many marriages as some of the other celebs on our list, but he has been married five times.
Gary Oldman
His first marriage was to actress Lesley Manville from 1987 until 1990, when he married Uma Thurman. They were together until 1992. In 1997, Oldman married Donya Fiorentino, but their marriage lasted until 2001. Finally, Oldman was married to Alexandra Edenborough from 2008 until 2015.
Rita Hayworth
Rita Hayworth is another classic Hollywood name that is still mentioned today, although her fame began decades ago. Her first marriage, which lasted from 1937 until 1942, was to Edward C. Judson. The actress was married to Orson Welles from 1943 to 1947.
Rita Hayworth
She married again after they divorced in 1949, this time to a royal figure, Prince Aly Khan, but they divorced in 1953. She married Dick Haymes again, but they divorced in 1955, followed by marriage to James Hill from 1958 to 1961.
James Cameron
James Cameron is one of the most well-known directors of all time, having directed films such as Avatar and Titanic. The filmmaker married Sharon Williams in 1978, however the marriage only lasted until 1984.
James Cameron
Cameron married Gale Ann Hurd the next year in a union that lasted until 1989. That same year, he started a marriage to Kathryn Bigelow that would end in 1991. After a few years, he married Linda Hamilton from 1997 to 1999, followed by Suzy Amis, his current wife, in 2000.