"Two and a Half Men" showcased Charlie Harper's philandering character and his various girlfriends. While some relationships were short-lived, a few were surprisingly compatible before he messed things up. Courtney was manipulative, Angie's daughter-in-law ruined their relationship, Kandi lacked intellectual compatibility, Lydia and Charlie's mother had similar controlling personalities, Rose was toxic, Sherri played hard to get, Linda was mature, Lisa had chemistry with Charlie but rejected him, Mia changed Charlie temporarily, and Chelsea had the best shot at changing him for good.