Ben Affleck & Matt Damon Have A Sexy Secret In Common— You'll Never Believe What!

Star connects Matt Damon, 45, and Ben Affleck, 43, through their shared romantic past – starting with Winona Ryder! Shortly after the two were introduced – by none other than Gwyneth Paltrow ­– back in December 1997, Matt and Winona, 44, reportedly became romantically involved. Sadly, the pair broke up three years later, only one month after the 2000 Golden Globes.

After Winona starred in Heathers with costar Christian Slater, 46, their on-screen chemistry soon turned into an off-set romance. The couple started dating in 1988, but soon broke things off that same year.

Long before Christian shared the stage with co-presenter Christina Applegate at the 2008 Emmy Awards, the two reportedly had a fling back in 1996. In July of 2015, however, the two denied ever having dated on the Late Late Show.

Christina did, however, briefly date Hollywood hottie Brad Pitt in 1989, before reportedly ditching him for another man!

Brad later publicly dated blonde-bombshell Gwyneth Paltrow, 43. The gorgeous couple ended up calling it quits on in June 1997, after five years of dating, after which Gwyn stated Brad was “too good” for her.

But Gwyneth didn’t stay single very long. The actress had an on-and-off relationship with Shakespeare in Love costar Ben Affleck, which lasted from 1997 to 2000. Gwyneth later stated in an interview with Diane Sawyer that Ben wasn’t in a "good place" to have a girlfriend when they were together.