15 Celebs Who Had the Same Ex

Hollywood is often described as a small town where everyone knows everyone else and this exclusivity extends to dating pools. Many high-profile stars have found themselves romantically linked to the same individuals as their peers or co-stars. While some of these overlapping relationships caused media frenzies and temporary feuds others were handled with grace and maturity. Looking back at these romantic connections offers a fascinating glimpse into the interconnected web of celebrity relationships. Here are fifteen pairs of famous figures who share a mutual ex-partner.

Selena Gomez & Miley Cyrus

These two Disney Channel icons share a history involving the youngest member of the Jonas Brothers. Nick Jonas dated Cyrus during the peak of her ‘Hannah Montana’ fame before entering a relationship with Gomez shortly after. The overlapping timeline reportedly caused some friction between the two teenage stars during the late 2000s. Both actresses have since confirmed there is no lingering bad blood regarding their shared teenage romance. They have both moved on to have highly successful music and acting careers independent of this early connection.

Jennifer Aniston & Angelina Jolie

The romantic history involving these two A-list actresses and Brad Pitt became one of the biggest tabloid stories of the 21st century. Aniston was married to Pitt for five years until their highly publicized separation in 2005. Pitt subsequently began a long-term partnership and eventual marriage with Jolie after they met on the set of ‘Mr. & Mrs. Smith’. The media perpetuated a narrative of rivalry between the two women for over a decade despite their silence on the matter. Both stars have continued to maintain successful careers while keeping their personal lives more private in recent years.

Taylor Swift & Katy Perry

These two pop superstars both had romantic relationships with singer-songwriter John Mayer. Swift dated Mayer briefly in 2009 and reportedly wrote the song ‘Dear John’ about the experience. Perry began an on-and-off relationship with Mayer several years later that lasted until 2014. While the two women experienced a well-known professional fallout they have since reconciled and put their differences aside. Their shared connection to Mayer remains a notable footnote in their respective dating histories.

Cameron Diaz & Kate Hudson

Cameron Diaz and Kate Hudson both spent time dating former professional baseball player Alex Rodriguez. Hudson was frequently seen cheering for Rodriguez at New York Yankees games during their relationship in 2009. Diaz began dating the athlete shortly after Hudson and Rodriguez split up. The two actresses have managed to maintain a friendship despite dating the same high-profile sports star. Rodriguez eventually moved on to other celebrity relationships including a long engagement to Jennifer Lopez.

Hilary Duff & Lindsay Lohan

The early 2000s saw a publicized feud between these teen idols over singer Aaron Carter. Carter dated Duff first but famously left her to date Lohan before returning to Duff. This back-and-forth created significant tension between the two young actresses that played out in teen magazines. Carter later admitted that he was at fault for creating the drama between the two stars. Both women eventually matured and left the teenage drama in the past.

Leonardo DiCaprio & Tom Brady

Hollywood actor Leonardo DiCaprio and NFL legend Tom Brady both had serious long-term relationships with supermodel Gisele Bündchen. DiCaprio and Bündchen dated for five years in the early 2000s and were considered one of the biggest couples of that era. After their split the Brazilian model met Brady and they eventually married and had two children together. Bündchen has spoken about how her time with DiCaprio was a period of personal growth. Both men remain at the top of their respective fields.

Nikki Reed & Nina Dobrev

These two actresses share a connection through their relationships with ‘The Vampire Diaries’ star Ian Somerhalder. Dobrev and Somerhalder dated for several years while co-starring on the hit supernatural drama. Reed later began dating Somerhalder and the couple eventually married and started a family. Despite rumors of awkwardness the three have been photographed together demonstrating a united and friendly front. They have actively dispelled myths about any feuds to support their mutual friends and partners.

Courteney Cox & Jennifer Aniston

Friends and co-stars Courteney Cox and Jennifer Aniston have maintained a close bond despite dating the same musician. Adam Duritz of the band Counting Crows dated Aniston briefly in the mid-1990s. He later entered a relationship with Cox that lasted much longer and included an appearance in the music video for ‘A Long December’. The two actresses remained best friends throughout these relationships and continue to be close today. Duritz has spoken fondly of his time with both women.

Heidi Klum & Mel B

Supermodel Heidi Klum and Spice Girl Mel B both share a romantic past with comedian Eddie Murphy. Mel B dated Murphy in 2006 and the relationship resulted in the birth of their daughter Angel. Klum later dated Murphy briefly following his split from the singer. The situation was complicated by paternity disputes involving Mel B and Murphy. Both women later worked together amicably as judges on the reality competition show ‘America’s Got Talent’.

Matt Damon & Johnny Depp

Winona Ryder was a prominent figure in the dating lives of both Matt Damon and Johnny Depp during the 1990s. Depp and Ryder were one of the most famous couples of the early 90s and were even engaged for a short period. Damon dated the actress several years later and they made a few public appearances together before splitting up. Both actors have since married other people and established families. Ryder remains a defining romantic connection for both men during their rise to stardom.

Taylor Swift & Selena Gomez

Singer Taylor Swift and actor Taylor Lautner briefly dated in 2009 after meeting on the set of ‘Valentine’s Day’. Interestingly Lautner also dated Swift’s close friend Selena Gomez prior to his relationship with the country-pop star. Gomez and Lautner were spotted together in Vancouver while they were both filming different projects. The three have managed to navigate these overlapping connections without public drama. Swift even wrote the apologetic song ‘Back to December’ about her breakup with Lautner.

Justin Timberlake & Colin Farrell

Pop star Britney Spears had high-profile relationships with both Justin Timberlake and Colin Farrell. Timberlake and Spears were the ultimate celebrity power couple of the late 90s until their abrupt breakup in 2002. Farrell was seen with Spears shortly after her split from Timberlake although he claimed they were just having fun. The media scrutiny surrounding Spears’ dating life was intense during both of these periods. Both men have since spoken about the pressure of dating in the public eye.

Ben Affleck & Marc Anthony

Ben Affleck and Marc Anthony both hold significant places in the life of Jennifer Lopez. Affleck and Lopez were engaged in the early 2000s before calling it off and then famously reuniting and marrying two decades later. Anthony was married to Lopez for ten years and they share twins Max and Emme. The two men have reportedly maintained a respectful relationship for the sake of the blended family dynamic. Lopez has described both relationships as pivotal chapters in her life.

Kristen Wiig & Drew Barrymore

Comedy stars Kristen Wiig and Drew Barrymore both dated The Strokes drummer Fabrizio Moretti. Barrymore was in a relationship with the musician for five years during the mid-2000s. Wiig began dating Moretti several years later and their relationship lasted for roughly 18 months. Barrymore publicly stated that the relationship between her ex and her friend seemed wacky but made sense. The two actresses have remained friendly and supportive of one another.

Kanye West & Nick Cannon

Reality TV star Kim Kardashian was romantically linked to both Nick Cannon and Kanye West. Cannon and Kardashian dated briefly in 2006 before her reality show became a global phenomenon. West and Kardashian were friends for years before they began dating and eventually married. The rapper and the television personality had four children together before their divorce. Cannon has frequently spoken positively about his past with Kardashian and her family.

Please share your thoughts on which celebrity pair surprised you the most in the comments.