Jake Gyllenhaal & Natalie Portman
There is not a clear beginning and ending to this former celebrity couple’s relationship, but they were first spotted together in 2002 and it is believed that they dated sometime between 2002 and 2006. Since then, both Portman and Gyllenhaal have moved on, but remain good pals. They even co-starred in the 2009 film Brothers together and their friendly, joking rapport was evident during the film’s promotion.