Charlie had a dreadful relationship with his mother Evelyn. From the beginning of the series, he ignored and despised her. In the Season 2 episode "Enjoy Those Garlic Balls", it was revealed why Charlie hated his mother. He believed that she's a narcissist who killed his father early, she married many men who don't even care about him and Alan and because she moved Charlie and his brother to an internship or boarding school or a camp or the Kibbutz in Israel where he and Alan got beat up because they weren't Jewish. In "We Called It Mr. Pinky", Charlie worries about his issues with his mother and how it could prevent him from having a long-term relationship. Over time, Charlie began to worry he might suffer from an unresolved Oedipal Complex towards his own mother (even accidentally seeing Evelyn's face in the place of his ex-girlfriend's face in bed after sex) and denies this over the series, though he does end up dating a certain woman who reminds him personality-wise of his own mother and the way she treats him and her children. Nevertheless, Evelyn and Charlie also had great moments. For example, in the episode "Did You Check With The Captain Of The Flying Monkeys?" Charlie told Evelyn that he loves her. Or also, in "Media Room Slash Dungeon" Charlie began to spend more time with his mother after he went to a party with her. In "Nice to Meet You, Walden Schmidt", Evelyn cried at Charlie's funeral (and apparently she was the only one) but also tried to earn money by telling everyone that she's got a beautiful house for rent.

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