Zach Braff and Florence Pugh (21 Years)
Actor and filmmaker, Zachary Israel Braff, has been a household name from his time playing J.D. on the hit television sitcom, “Scrubs” in the early 2000’s. He first met fellow actor Florence Pugh online, and the two then worked on a film together where they clicked and began dating. This led to criticism from online trolls for which Pugh responded that she was old enough to date who she wanted, regardless if that person was a quarter of a century older than she. The couple managed to make things work for three-years before calling it quits.