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Over time, several supporting characters have been promoted to starring roles: Berta (season 1 recurring; season 2–12 regular), Charlie and Alan's (and later Walden's) sharp-tongued housekeeper; Kandi (season 3 recurring; season 4 regular; season 10 guest), one of Charlie's former one night stands, and later on, Alan's second ex-wife; Chelsea (season 6 recurring; season 7 regular; season 9 guest), Charlie's second most notable love interest (after Rose), and ex-fiancée; Walden Schmidt (season 9–12), an internet billionaire who buys Charlie's beach house after his death; Jenny (season 11–12), Charlie's illegitimate daughter from a one-night stand twenty years before; last of all, Louis (season 12), the 6-year-old boy that Walden decides to adopt.
Melissa walks in on them, but Alan is too high to explain what happened. In the season six finale, while Judith is giving birth to what is possibly Alan's daughter, Alan and Melissa meet up and have sex in a closet, ultimately getting back together.Before returning to the afterlife, Charlie tries to reveal himself to Jake but fails.As a result of retroactive continuity, the series finale reveals that Charlie never died but has been held captive by Rose in a basement pit under her house in Sherman Oaks.Also, in the Season 6 episode, "She'll Still Be Dead at Halftime", he confesses that he likes feet (see foot fetish).In the season 3 finale, Alan marries a twenty-two-year-old dumbbell named Kandi who was one of Charlie's former girlfriends.Their relationship goes into season seven where Melissa wants to move into the beach house with Alan, Charlie, and Chelsea.
Alan is happy to live with Melissa at first, but eventually Melissa and Chelsea start taking over the house, resulting in Alan and Charlie staying at a hotel. Evelyn tells Chelsea about Melissa's short lived romance resulting in the girls getting into a fight, and Melissa moving out.
After Charlie had canceled his wedding with Mia, Alan and Kandi got married instead.
Although in the season 4 premiere, four months after the marriage Kandi throws Alan out of her condo and divorces Alan which leads him to paying alimony to two ex-wives.
Alan and Melissa are now forced to have sex in their car since Melissa won't let Alan see her mother at her house, and Melissa doesn't want to see Chelsea at Alan's house.
Melissa tells Alan to get his own house, so Alan steals the keys to a house Evelyn is selling, and lies to Melissa, saying that it's his.
He escapes, collects $2.5 million in royalty money from his children's songs, and sends Alan, Evelyn and Walden, who Rose has told him about, texts and emails promising revenge while also sending large checks to his former romantic interests, Jenny, and Jake.