Celebrities Who Have Had The Most Relationships And Their Notable Exes

In the glitzy world of Hollywood, relationships are often as captivating as the movies and music that made these celebrities famous. From whirlwind romances to high-profile breakups, the love lives of stars are a subject of constant fascination for fans around the globe. But which celebrities have had the most relationships?

Let’s delve into the dating history of some of the biggest names in entertainment.

Scarlett Johansson (Rumored number of Exes: 11)

Scarlett Johansson, known for her roles in blockbuster films and her timeless beauty, has had her fair share of romantic entanglements. From fellow actors to musicians, Johansson’s dating history reflects her status as one of Hollywood’s most desirable leading ladies.

• Jack Antonoff (2001–2002)
  • Musician. They dated in high school before both became famous.
• Jared Leto (2004)
  • Actor and musician. They were seen together on several occasions, sparking dating rumors.
• Benicio del Toro (2004)
  • Actor. Rumors of a brief fling started after an encounter at the Chateau Marmont.
• Patrick Wilson (2004)
  • Actor. They were rumored to be dating around the time they worked together on A Love Song for Bobby Long.
• Josh Hartnett (2005–2007)
  • Actor. They dated for about two years before parting ways due to busy schedules.
• Ryan Reynolds (2007–2011)
  • Actor. They were married in 2008 but divorced in 2011.
• Sean Penn (2011)
  • Actor. They had a brief relationship and were spotted at various events together.
• Nate Naylor (2011–2012)
  • Ad executive. Their relationship was relatively low-profile but confirmed.
• Romain Dauriac (2012–2016)
  • Journalist. They married in 2014 and had a daughter together before divorcing in 2017.
• Kevin Yorn (2017)
  • Entertainment lawyer. They were rumored to be dating but remained close friends.
• Colin Jost (2017–present)
  • Comedian and writer. They began dating in 2017, got engaged in 2019, and married in October 2020.

Kendall Jenner (Rumored number of Exes: 12)

Kendall Jenner, the supermodel and reality TV personality, has had her fair share of high-profile relationships. Known for keeping her personal life relatively private compared to her famous siblings, Jenner has been linked to various celebrities, including basketball players and fellow musicians.

• Julian Brooks (2012–2013)
  • High school boyfriend. They dated while Kendall was still in high school.
• Harry Styles (2013–2014, 2015–2016)
  • Former One Direction member. Their relationship included a public Caribbean yacht holiday.
• Chandler Parsons (2014)
  • NBA player. They were spotted dining together, sparking dating rumors.
• Lewis Hamilton (2015)
  • Formula 1 driver. They were seen together at multiple events, including the Monaco Grand Prix.
• Jordan Clarkson (2016)
  • NBA player. They were often seen together in Los Angeles.
• A$AP Rocky (2016–2017)
  • Rapper. Their relationship included public appearances at events and fashion shows.
• Blake Griffin (2017–2018)
  • NBA player. They dated for several months and were seen together frequently.
• Anwar Hadid (2018)
  • Model and younger brother of Gigi and Bella Hadid. They were seen kissing at a party.
• Ben Simmons (2018–2019)
  • NBA player. Their relationship was on-and-off, including public sightings and social media posts.
• Kyle Kuzma (2019)
  • NBA player. They were seen together on a yacht over the Fourth of July weekend.
• Devin Booker (2020–2022)
  • NBA player. Their relationship was confirmed through social media and public outings.
• Bad Bunny (2023)
  • Musician. Rumors began in early 2023 after they were seen together in public.

Rihanna (Rumored number of Exes: 13)

Rihanna, the Barbadian singer and fashion icon, is known for her chart-topping hits and bold sense of style. Alongside her musical achievements, Rihanna’s romantic life has been the subject of much speculation, with a long list of high-profile relationships with fellow musicians, athletes, and actors.

• Chris Brown (2007–2013)
  • Singer. Rihanna’s most high-profile relationship, marked by controversy after Chris Brown physically assaulted her in 2009.
• Josh Hartnett (2007)
  • Actor. They were rumored to have dated briefly after being spotted together in London.
• Drake (2009, 2010, 2016)
  • Rapper. Rihanna and Drake’s relationship was an on-and-off affair over several years, with collaborations on music and public appearances fueling speculation.
• Matt Kemp (2010–2011)
  • MLB player. They dated for about a year, with their relationship being relatively private compared to her other romances.
• Dudley O’Shaughnessy (2011)
  • Boxer and model. They met on the set of her music video for “We Found Love” and were briefly linked romantically.
• Ashton Kutcher (2012)
  • Actor. Rumored to have had a fling in early 2012 after being spotted leaving his house late at night.
• Travis Scott (2015)
  • Rapper. They were rumored to have dated briefly, though neither confirmed the relationship.
• Lewis Hamilton (2015)
  • Formula 1 driver. They were seen together at events, sparking dating rumors.
• Leonardo DiCaprio (2015)
  • Actor. They were seen together at a few parties, but their relationship was never confirmed.
• Karim Benzema (2015)
  • Soccer player. They were rumored to be dating after being spotted together in New York.
• Drake (again) (2016)
  • Rapper. After their initial breakup, Rihanna and Drake rekindled their romance briefly in 2016.
• Hassan Jameel (2017–2020)
  • Saudi businessman. They had a relatively private relationship, rarely seen together in public.
• A$AP Rocky (2021–present)
  • Rapper. Rihanna and A$AP Rocky confirmed their relationship in 2021 after months of speculation.

Kim Kardashian (Rumored number of Exes: 15)

As one of the most recognizable faces in popular culture, Kim Kardashian’s love life has been a constant topic of discussion in the media. From her highly-publicized marriage to Kanye West to her previous relationships with athletes and musicians, Kardashian’s romantic escapades have played out in the public eye for years.

• T.J. Jackson (1995–1999)
  • Musician. Kim’s first known boyfriend; they dated during high school.
• Damon Thomas (2000–2004)
  • Music producer. Kim’s first husband; they married in 2000 and divorced in 2004.
• Ray J (2005–2007)
  • Singer. Their relationship became widely known due to the release of their sex tape.
• Nick Lachey (2006)
  • Singer. They briefly dated after Nick’s divorce from Jessica Simpson.
• Nick Cannon (2006–2007)
  • Actor and musician. They dated for a few months before splitting.
• Reggie Bush (2007–2009, 2010)
  • NFL player. They had an on-and-off relationship over three years.
• Miles Austin (2010)
  • NFL player. Their relationship lasted a few months in the summer of 2010.
• Gabriel Aubry (2010)
  • Model. They dated briefly towards the end of 2010.
• Kris Humphries (2010–2011)
  • NBA player. They had a whirlwind romance, got engaged, and married in August 2011, but the marriage lasted only 72 days before Kim filed for divorce.
• Kanye West (2012–2021)
  • Rapper and fashion designer. Kim and Kanye were friends for years before they started dating in 2012. They married in 2014, had four children together, and their relationship ended in divorce in 2021.
• Van Jones (2021)
  • Activist and CNN commentator. Rumors circulated about their relationship following Kim’s divorce filing, but these were never confirmed.
• Pete Davidson (2021–2022)
  • Comedian. They started dating after Kim hosted Saturday Night Live in October 2021 and ended their relationship in August 2022.
• Mehmet “Mystery Man” Akif Alakurt (2022)
  • Rumored. A brief rumored romance around late 2022.
• Freddy Naga (2022–2023)
  • Entrepreneur. Rumored relationship with speculation about a new romance in early 2023.
• Tom Brady (2023)
  • NFL player. Speculation about a relationship surfaced in 2023, though not confirmed.

Emma Watson (Rumored number of Exes: 16)

From her early days as Hermione Granger in the “Harry Potter” series to her later roles as a women’s rights activist and acclaimed actress, Emma Watson has captivated audiences worldwide. Alongside her professional success, Watson’s romantic life has also garnered attention, with a list of exes that includes fellow actors and businessmen.

• Tom Ducker (2006–2007)
  • Rugby player. Emma’s first public relationship was with Tom during her teen years.
• Angus Willoughby (2007–2008)
  • Drama student. They met while Emma was studying at the Royal Academy of Dramatic Art.
• Francis Boulle (2008)
  • Reality TV star and businessman. They dated briefly before Francis decided to focus on his career.
• Jay Barrymore (2008–2009)
  • Financier. They dated for about a year before breaking up due to long distance.
• Rafael Cebrián (2009–2010)
  • Actor and musician. They were classmates at Brown University and were seen together often.
• George Craig (2010)
  • Model and musician. They met while filming a Burberry ad campaign and briefly dated.
• Johnny Simmons (2011)
  • Actor. They met on the set of The Perks of Being a Wallflower and had a short romance.
• Will Adamowicz (2011–2013)
  • Oxford student. They met at Oxford University and dated for almost two years.
• Matthew Janney (2013–2014)
  • Rugby player. They dated for a year while Emma was attending Oxford.
• Roberto Aguire (2015)
  • Actor. They met during the filming of Harry Potter and the Goblet of Fire and reconnected later.
• William “Mack” Knight (2015–2017)
  • Tech entrepreneur. Their relationship was kept very private and lasted about two years.
• Chord Overstreet (2018)
  • Actor. They dated briefly in 2018 but broke up after a few months.
• Brendan Wallace (2018–2019)
  • Tech CEO. They were spotted together on holiday and had a short-lived relationship.
• Cole Cook (2019)
  • Entrepreneur and brother of Alicia Keys. They were seen together, leading to dating rumors.
• Leo Robinton (2019–2021)
  • Businessman. They dated for over two years, keeping their relationship mostly private.
• Brandon Green (2022–present)
  • Businessman. Son of British retail billionaire Sir Philip Green. They were first linked in 2022 and have been seen together in various public outings.

Paris Hilton (Rumored number of Exes: 16)

Paris Hilton, the heiress and media personality, has lived her love life in the limelight. Known for her high-profile engagements and breakups, Hilton’s dating history includes actors, musicians, and businessmen. Her relationships often made headlines, contributing to her status as a tabloid favorite and reality TV star.

• Rick Salomon (2001–2003)
  • Professional poker player. Known for their infamous sex tape, which brought Paris into the media spotlight.
• Jason Shaw (2002–2003)
  • Model and actor. They were engaged for a brief period but ended their relationship amicably.
• Deryck Whibley (2003)
  • Musician. They dated briefly; Deryck is the lead singer of Sum 41.
• Nick Carter (2004)
  • Singer. They dated for several months, and their relationship ended with a public breakup.
• Simon Rex (2004)
  • Actor and comedian. Rumored to have dated briefly after meeting in Hollywood.
• Paris Latsis (2004–2005)
  • Greek shipping heir. They were engaged but called off the engagement after several months.
• Stavros Niarchos (2005–2006)
  • Greek shipping heir. Known for their on-and-off relationship, which was highly publicized.
• Josh Henderson (2007)
  • Actor. They were spotted together several times, leading to dating rumors.
• Jared Leto (2008)
  • Actor and musician. They were seen together at several events, sparking relationship rumors.
• Benji Madden (2008)
  • Musician. They dated for nine months and were very public about their relationship.
• Doug Reinhardt (2009–2010)
  • Reality TV star and baseball player. They had an on-and-off relationship that ended in a public breakup.
• Cy Waits (2010–2011)
  • Nightclub owner. They dated for a year, and he appeared on her reality show The World According to Paris.
• River Viiperi (2012–2014)
  • Model. They dated for nearly two years and often posted about their relationship on social media.
• Thomas Gross (2015–2016)
  • Businessman. They had a year-long relationship and traveled extensively together.
• Chris Zylka (2017–2018)
  • Actor. They were engaged in early 2018 but called off the engagement later that year.
• Carter Reum (2019–present)
  • Entrepreneur and venture capitalist. They began dating in 2019, got engaged in February 2021, and married in November 2021. They welcomed their first child via surrogate in January 2023.

Taylor Swift (Rumored number of Exes: 19)

The queen of breakup anthems, Taylor Swift’s love life has been a frequent topic of speculation and inspiration for her chart-topping songs. With a string of highly-publicized relationships with fellow musicians and actors, Swift has never been shy about expressing her feelings through her music.

• Joe Jonas (July–October 2008)
  • Member of the Jonas Brothers. Their breakup was famously short, ending over a phone call.
• Lucas Till (March–April 2009)
  • Actor. They met on the set of the music video for “You Belong with Me.”
• Taylor Lautner (August–November 2009)
  • Actor. Their relationship inspired the song “Back to December.”
• John Mayer (December 2009–February 2010)
  • Singer-songwriter. Their brief relationship led to the song “Dear John.”
• Cory Monteith (April–May 2010)
  • Actor. Rumored to have dated briefly before he passed away in 2013.
• Jake Gyllenhaal (October 2010–January 2011)
  • Actor. Their relationship was the inspiration behind several songs on the album Red.
• Adam Young (February 2011)
  • Singer (Owl City). He was rumored to be the subject of the song “Enchanted.”
• Chord Overstreet (March 2011)
  • Actor. They were spotted together on a date, sparking rumors.
• Garrett Hedlund (April–May 2011)
  • Actor. Briefly rumored to be dating after being seen together.
• Eddie Redmayne (October 2011–February 2012)
  • Actor. Reportedly dated during her audition for Les Misérables.
• Zac Efron (February 2012)
  • Actor. They were linked around the time of their film The Lorax promotion.
• Conor Kennedy (July–October 2012)
  • Member of the Kennedy family. They had a summer romance and were often seen in public together.
• Harry Styles (December 2012–January 2013)
  • Former One Direction member. Their relationship inspired songs like “Style” and “Out of the Woods.”
• Calvin Harris (March 2015–June 2016)
  • DJ and music producer. Their relationship was public, with many photos and social media posts together.
• Tom Hiddleston (June–September 2016)
  • Actor. Known for their whirlwind romance that included high-profile trips and public appearances.
• Joe Alwyn (May 2017–April 2023)
  • Actor. A long-term relationship that was more private, with occasional public sightings and songs likely inspired by him.
• Matty Healy (May 2023–June 2023)
  • Lead singer of The 1975. Rumored to be dating briefly during her “Eras” tour.
• Fernando Alonso (April 2023–June 2023)
  • Formula 1 driver. Rumors of them dating emerged but were not confirmed.
• Travis Kelce (October 2023–Present)
  • NFL player. Their relationship became a significant media topic, especially with Taylor attending his games.

Madonna (Rumored number of Exes: 23)

Madonna, the pop icon known for her trailblazing music career and provocative persona, has had numerous high-profile romances over the decades. Her relationships span musicians, actors, and models, reflecting her influential and eclectic presence in the entertainment world. From her tumultuous marriage to Sean Penn to her relationship with Guy Ritchie, Madonna’s love life has been as dynamic as her career.

• Dan Gilroy (1979–1980)
  • Musician. He was Madonna’s first significant boyfriend when she moved to New York and started her music career.
• Mark Kamins (1981–1982)
  • DJ and producer. He produced her first single, “Everybody,” and they had a brief romantic relationship.
• Jean-Michel Basquiat (1982)
  • Artist. They dated for a short period; Basquiat was a famous painter and a significant figure in the New York art scene.
• Ken Compton (1982–1983)
  • Waiter and musician. He was briefly involved with Madonna during her early days in New York.
• Jellybean Benitez (1983–1985)
  • DJ and producer. They collaborated on her early hits and had a personal relationship.
• John “Jellybean” Benitez (1983–1984)
  • DJ and music producer. They dated and worked together on her music.
• Sean Penn (1985–1989)
  • Actor. They were married from 1985 to 1989, a period marked by intense media scrutiny and a tumultuous relationship.
• Warren Beatty (1989–1990)
  • Actor and director. They dated while filming Dick Tracy and made several public appearances together.
• Tony Ward (1990–1991)
  • Model and actor. He starred in her music video for “Justify My Love” and they had a brief relationship.
• Vanilla Ice (1991–1992)
  • Rapper. They dated for about eight months and he appeared in her Sex book.
• Carlos Leon (1994–1997)
  • Personal trainer. They had a daughter, Lourdes Leon, in 1996 and remained close after their breakup.
• Dennis Rodman (1994)
  • NBA player. They had a brief and highly publicized relationship.
• Andy Bird (1997–1998)
  • Businessman. They dated for a short period in the late 1990s.
• David Blaine (1998)
  • Magician. They were rumored to have had a brief fling.
• Guy Ritchie (1999–2008)
  • Film director. They married in 2000 and had a son, Rocco, and adopted a son, David. They divorced in 2008.
• Alex Rodriguez (2008)
  • MLB player. Rumors of their affair circulated while he was still married, though they never confirmed a serious relationship.
• Jesus Luz (2008–2010)
  • Model. They dated following her divorce from Guy Ritchie, with a notable age difference between them.
• Brahim Zaibat (2010–2013)
  • Dancer. They had a relationship lasting about three years, during which they worked together on her tours.
• Timor Steffens (2014)
  • Dancer. They dated for about a year and were often seen together at events.
• Kevin Sampaio (2017)
  • Model. Rumored to be dating briefly after meeting during the shooting of a music video.
• Ahlamalik Williams (2018–2022)
  • Dancer. They started dating in 2018 after he joined her tour as a backup dancer and split in 2022.
• Andrew Darnell (2022–2023)
  • Model. They dated briefly following her split from Ahlamalik Williams.
• Josh Popper (2023)
  • Boxing coach. They started dating in 2023 and have been seen together in public.

Lindsay Lohan (Rumored number of Exes: 24)

With a career that began in childhood and included both critical acclaim and public controversies, Lindsay Lohan’s personal life has been as tumultuous as her professional journey. From Hollywood heartthrobs to industry insiders, Lohan’s extensive dating history has been well-documented in the tabloids over the years.

• Aaron Carter (2002–2003)
  • Singer. They were teenage sweethearts, and their relationship was highly publicized.
• Wilmer Valderrama (2004–2006)
  • Actor. They had an on-and-off relationship for a couple of years, which attracted significant media attention.
• Jared Leto (2005)
  • Actor and musician. They were rumored to have dated briefly.
• Harry Morton (2006–2007)
  • Restaurateur. They dated for about a year, and their relationship was closely followed by the media.
• Calum Best (2007–2008)
  • Reality TV star. They had an on-and-off relationship that played out in the tabloids.
• Riley Giles (2007)
  • Snowboarder. They briefly dated while Lohan was in rehab.
• Samantha Ronson (2008–2009)
  • DJ. One of Lohan’s most high-profile relationships, their tumultuous romance attracted intense media scrutiny.
• Eilat Anschel (2010)
  • Israeli military officer. They were briefly linked in 2010.
• Vikram Chatwal (2011)
  • Hotelier. They were rumored to have dated, but the relationship was not confirmed.
• Terry Richardson (2012)
  • Photographer. They were rumored to have had a fling, but it was never confirmed.
• Max George (2012)
  • Singer (The Wanted). They were briefly linked in late 2012.
• Gavin Doyle (2013)
  • Fitness trainer. They were spotted together, sparking dating rumors.
• Avi Snow (2013)
  • Musician. They were briefly linked in early 2013.
• Morgan O’Connor (2013)
  • Model. They were seen together at events, but their relationship status was unclear.
• Mathia Milani (2013)
  • Model. They were rumored to have dated briefly.
• Christian Arno Williams (2016)
  • Businessman. They were seen together, but their relationship was not confirmed.
• Je-yong Ha (2017)
  • South Korean bodybuilder. They were seen together on social media, sparking dating rumors.
• Dennis Papageorgiou (2016)
  • Restaurateur. They were seen together after Lohan’s breakup with Egor Tarabasov.
• Egor Tarabasov (2016)
  • Russian businessman. Lohan was engaged to Tarabasov, but their relationship ended amid allegations of abuse.
• Bader Shammas (2018)
  • Saudi prince. They were rumored to be dating, but their relationship was not confirmed.
• Javier Bardem (2019)
  • Actor. They were spotted together at an event, sparking dating rumors.
• Antonino Barbagallo (2020)
  • Businessman. They were rumored to be dating, but their relationship status was unclear.
• Matthias Vriens-McGrath (2020)
  • Photographer. They were rumored to be dating, but their relationship was not confirmed.
• Bader Shammas (again) (2021)
  • Saudi prince. They were rumored to have rekindled their romance, but it was not confirmed.

While these celebrities may have had their fair share of relationships, it’s important to remember that love in the spotlight comes with its own set of challenges. Despite the ups and downs, these stars continue to capture our attention both on and off the screen, reminding us that when it comes to matters of the heart, even the rich and famous are not immune to the trials and tribulations of romance.

Read also: 8 Things to avoid these in any romantic relationship