The movie Two Lovers focuses on the main character, Leonard, played by Joaquin Phoenix. Leonard is a quiet man who lives with his parents. Lately, his life has not been everything he would like, and he has attempted to commit suicide several times. Each time has been unsuccessful. Hoping to make his life a bit more interesting, Leonard's parents set him up with the daughter of their business partner. The daughter, Sandra, is sweet and somewhat na´ve and immediately takes a liking to Leonard.
Leonard confesses that he is also interested in Sandra, and the pair begins spending more time together, forming a close romantic relationship. However, as his relationship with Sandra become more serious, Leonard meets and falls in love with his neighbor, Michelle. Michelle is a beautiful, passionate woman but is having some life issues. She has a serious drug problem and is also often depressed because the man she loves is married to another woman and refuses to leave him.
Leonard tells Michelle that he cares for her and attempts to win her favor in any way possible. Michelle begins to rely more and more on Leonard, and starts to care for him as well. However, although she is upset with her boyfriend, she is still deeply in love with him and is not ready to turn to Leonard completely. Meanwhile, as Leonard falls more and more in love with Michelle, he continues to carry on his relationship with Sandra. Things become even more complicated when Leonard and Sandra's parents realize that the two young people have become a couple. Both sets of parents begin pushing for a marriage proposal, and Leonard becomes trapped between the two women he cares for.
As the story progresses, Leonard learns more about Michelle's secrets but also attempts to stay by Sandra's side, causing a very interesting but stressful situation.