Matt Dillon
Matt Dillion is one of the teenage success stories in Hollywood that has had leading roles in blockbuster movies across several decades. However, his massive success on the screen does not translate to marital bliss. He has dated several girls over the years, including Cameron Diaz in the 90s. His most recent affair started in 2014 with Roberta Mastromichele. Perhaps, this latest relationship will end in marriage. You can never tell.