The Devastating TV Breakups We Still Can't Get Over

Things start to go south for Jess Mariano (Milo Ventimiglia) and Rory Gilmore (Alexis Bledel) towards the end of their senior year, as the couple deal with Rory's jealous ex, Dean (Jared Padalecki), trying to break them apart. Jess is also secretive, withholding crucial information about his future: He's not only failing high school; his very presence in Stars Hollow is crucially at stake. What Rory doesn't know is that Jess's uncle, Luke, will only permit him to stay in town if he can graduate.

With tensions high due to Jess' unwillingness to confide in his girlfriend, he and Rory get into an explosive fight. The following day, Jess meets his estranged father for the first time and ends up leaving town without giving Rory notice at all, meaning he doesn't take her to prom or come to graduation. Though they briefly encounter each other again in later seasons, their final break comes as Rory speaks to a wordless Jess on the phone, saying goodbye with a heartbreaking revelation: "I think I may have loved you, but I just need to let it go."