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What do these three have in common? They have dated two (or more) of Hollywood’s biggest celebrities! Check out our list of stars who dated the same person. You might be surprised by just how romantically connected Tinseltown is. - Xfinity Entertainment Programmers (Photos: Alberto E. Rodriguez, Pascal Le Segretain/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
It's a Small Wor...What do these three have in common? They have dated two (or more) of Hollywood’s biggest celebrities! Check out our list of stars who dated the same person. You might be surprised by just how romantically connected Tinseltown is. - Xfinity Entertainment Programmers (Photos: Alberto E. Rodriguez, Pascal Le Segretain/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Brad Pitt and Be...What do Brad Pitt and Ben Affleck have in common besides good looks and super skills on the silver screen? One particular blonde actress... - Xfinity Entertainment Programmers (Photos: Kevork Djansezian, Alberto E. Rodriguez/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Gwyneth PaltrowGwyneth Paltrow! Long before he bought a ring for Angelina, Brad got down on one knee and proposed to Gwyneth in 1994. She eventually broke off the engagement and began a three-year, on-and-off relationship with Ben Affleck. Paltrow is now married to Coldplay frontman Chris Martin. - Xfinity Entertainment Programmers (Photo: Pascal Le Segretain/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Matthew McConagh...At first glance, it may seem that Canadian heartthrob Ryan Gosling and Texas hunk Matthew McConaughey are total opposites... - Xfinity Entertainment Programmers (Photos: Andreas Rentz, Frazer Harrison/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Sandra BullockBut they do have one thing in common… both guys won over America’s sweetheart. Sandra Bullock and Matthew dated for two years in the late 1990s. She moved on to Ryan a few years later, but their love didn’t last. - Xfinity Entertainment Programmers (Photo: Jason Merritt/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Cameron Diaz and...These two blondes don’t just compete for movie roles... - Xfinity Entertainment Programmers (Photos: Alberto E. Rodriguez, Pascal Le Segretain/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Alex RodriguezThey compete for the same men! Diaz and Hudson both seriously dated Yankees player Alex Rodriguez, but neither relationship panned out. - Xfinity Entertainment Programmers (AP Photo/Kathy Willens) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Jennifer Aniston...These two are more than just best “Friends.” Aniston and Cox also have the same taste in men. - Xfinity Entertainment Programmers (Photos: Jason Merritt, Mike Coppola/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Adam DuritzBoth ladies dated Counting Crows frontman Adam Duritz during the 1990s. Cox even appeared in his band’s music video for the song "A Long December" in 1997. - Xfinity Entertainment Programmers (Photo: Dario Cantatore/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Jennifer Lopez a...At first glance, these two couldn’t be more different, but look a little closer. One is a saucy singer with film experience, the other a bona fide movie star with a little musical work under her belt. They also dated the same guy... - Xfinity Entertainment Programmers (Photos: Christopher Polk, Mike Coppola/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Bradley CooperPeople's "Sexiest Man of the Year," actor Bradley Cooper! The French-speaking hunk swept both ladies off their feet. - Xfinity Entertainment Programmers (Photo: Alberto E. Rodriguez/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Demi Lovato and ...Who was suave enough to land former Disney star Demi Lovato and the sweet Mandy Moore? - Xfinity Entertainment Programmers (Photos: Frazer Harrison, David Livingston/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Wilmer Valderram..."That '70s Show" star Wilmer Valderrama! Fez is currently dating Derek Jeter's ex, "Friday Night Lights" babe Minka Kelly. Lucky guy. - Xfinity Entertainment Programmers (Photo: Kevin Winter/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Johnny Depp and ...Which 1990s leading lady did Johnny Depp and Matt Damon both romance? - Xfinity Entertainment Programmers (Photos: Pascal Le Segretain, Andrew H. Walker/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Winona RyderIt is Winona Ryder! Depp and Ryder were engaged in the early 1990s, resulting in Johnny’s infamous “Winona Forever” tattoo. She picked up with Matt Damon in the early 2000s, but their love fizzled shortly after. - Xfinity Entertainment Programmers (Photo: Jason Merritt/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
George Clooney a...There is one Hollywood goddess that won the heart of both Charlie Sheen and George Clooney. - Xfinity Entertainment Programmers (Photos: Gareth Cattermole, Michael Loccisano/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Kelly PrestonKelly Preston! John Travolta’s current wife dated both men in the late 1980s and early 1990s. Clooney gifted Preston with a pet pig named Max, an animal he kept long after their split. Her relationship with Sheen ended in 1990 when he accidentally shot her in the leg. - Xfinity Entertainment Programmers (Photo: Michael Loccisano/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Jessica Simpson ...Jessica Simpson and Carrie Underwood battle it out on the charts and in the love department. See which guy won over both country cuties... - Xfinity Entertainment Programmers (Photos: Jamie McCarthy, Jason Merritt/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Tony RomoNFL player Tony Romo! The Cowboys QB had a highly publicized relationship with Jessica Simpson from 2007 until 2009. Romo courted Carrie Underwood for a few months before finding true love with now-wife Candice Crawford. The pair recently welcomed a baby boy. - Xfinity Entertainment Programmers (AP Photo/Julio Cortez) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
Warren Beatty an...We know... finding a similarity between Academy Award winner Warren Beatty and rapper Vanilla Ice is seemingly impossible. But look no further than a certain pop legend... - Xfinity Entertainment Programmers (Photos: Jason Merritt, Ian Gavan/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
MadonnaMadonna! Madge began dating Beatty after meeting on the set of “Dick Tracy.” The pair recorded a duet, "Now I'm Following You," for her 1990 album “I'm Breathless.” The relationship ended the very next year, but Madonna wasn’t heartbroken for very long. She quickly began (and ended) an eight-month romance with rapper Vanilla Ice. - Xfinity Entertainment Programmers (Photo: Stephen Lovekin/Getty) The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.
