Celebrity Couples Who Almost Made It Work Long Term And Then Destroyed Our Faith In Love

Jon Hamm And Jennifer Westfeldt

Photo Credit: Chris Polk / Getty Images

Jon Hamm and Jennifer Westfeldt were in a happy, unmarried relationship for 18 years. The couple first met at an L.A. party in the late 90s. Hamm later had a small role in Kissing Jessica Stein, a film that Westfeldt co-wrote and starred in.

Jon has been honest with the press about his struggles with alcoholism and his troubled past. In many ways, he isn’t too different from Don Draper, the character that made his career. A source told People magazine, “He has always had demons and needed a mother figure in his life. It was generally assumed that they would break up once he got sober, because he didn’t need to lean on her to take care of him so much.”