Celebrities Who Dated the Same People

Leonardo DiCaprio and Blake Lively

Leo romanced Blake for a few short months back in the Spring and Summer of 2011. After getting cozy all over the South of France during the Cannes Film Festival, the pair were spotted sightseeing in Italy, holding hands in LA, and grabbing lunch in Santa Monica. The two then called it quits that October.

1 / 12

Blake Lively and Ryan Reynolds

Image Source: Getty / Mike Coppola

After her fling with Leo, Blake went on to date and eventually marry her Green Lantern costar Ryan Reynolds. They tied the knot in a low-key ceremony in South Carolina in 2012 and are the proud parents of two adorable daughters.

2 / 12

Ryan Reynolds and Scarlett Johansson

Image Source: Getty / Kevin Mazur

Ryan and Scarlett married in September 2008, less than two years after he ended his engagement to Alanis Morissette. The extremely private couple were rarely seen together and eventually announced their separation in December 2010. Shortly after the split, the actor opened up about their breakup, saying he went through "a lot of pain."

3 / 12

Scarlett Johansson and Jared Leto

Image Source: FameFlynet

Long before her marriage to Ryan, Scarlett briefly dated Jared Leto in early 2004. The two were spotted locking lips and getting cozy on multiple occasions, but things fizzled out quickly.

4 / 12

Jared Leto and Paris Hilton

Image Sources: Getty / Jason Merritt and Getty / Frederick M. Brown

Jared, who has had many famous girlfriends, may not have been in an "official" relationship with Paris Hilton, but the two definitely hooked up. Pictures surfaced of the pair engaging in a steamy makeout session while partying at Hyde Lounge during the 2008 Sundance Film Festival.

5 / 12

Paris Hilton and Benji Madden

Image Source: Getty / Ethan Miller

One of Paris's more serious romances was with Good Charlotte rocker Benji Madden. The couple dated for more than nine months back in 2008 and were frequently photographed getting affectionate while out and about together.

6 / 12

Benji Madden and Cameron Diaz

Image Source: Getty / Noel Vasquez

Benji went on to find his happy ending with actress Cameron Diaz. The two started dating in May 2015, got engaged a few days before Christmas that same year, and tied the knot in a surprise ceremony at their LA home just 17 days later.

7 / 12

Cameron Diaz and Justin Timberlake

Image Source: Getty / Alexander Tamargo

Before her marriage to Benji, Cameron began dating Justin Timberlake after they met backstage at the Nickelodeon Kids' Choice Awards in 2003. Their romance was speculated to constantly be on and off, and they eventually called it quits for good in December 2006. The pair have remained close over the years, even starring in Bad Teacher together in 2011. (Fun fact: Cameron also dated Jared Leto from 1999 until 2003.)

8 / 12

Justin Timberlake and Britney Spears

Image Source: Getty / KMazur

In what has to be considered one of Hollywood's most iconic couples, Justin began dating his former Mickey Mouse Club costar and childhood sweetheart, Britney Spears, back in 1999. The two made numerous cute appearances together before abruptly breaking up in March 2002. Rumors swirled that the split was caused by infidelity on Britney's part, and while songs from both parties seem to back that up, neither has ever confirmed it.

9 / 12

Britney Spears and Colin Farrell

Image Source: Getty / Kevin Winter

Britney had a brief fling with Irish actor Colin Farrell in 2003 . . . and by brief, we mean they may have only had one date. The two got extremely flirty on the red carpet at the premiere of his film The Recruit and were later seen on the balcony of his hotel room.

10 / 12

Colin Farrell and Amelia Warner

Image Source: Getty / Barry King

Back in his bad-boy days, Colin was involved with British actress and singer Amelia Warner. The pair's romance, which only lasted from July until November 2001, was quite intense. During a vacation to Tahiti, they married on the beach in a ceremony that wasn't legally binding. Colin also got a tattoo of Amelia's name around his ring finger.

11 / 12

Amelia Warner and Jamie Dornan

Image Source: Getty / David M. Benett

Amelia went on to marry Fifty Shades Darker actor Jamie Dornan in April 2013. That June, they announced they were expecting their first child, and the actress gave birth to daughter Dulcie in November. The couple also recently welcomed their second child together in March 2016.

12 / 12