- Season 9 ... - Two And A Half Men

Walden allows Alan Harper (Jon Cryer) and his son Jake (Angus T. Jones) to move back in, forming a new "surrogate family". Alan takes on a mentor role, helping the naive Walden navigate his divorce and the dating world. Key Cast & Characters Role in Season 9 Jon Cryer Alan Harper Now lives with Walden; struggles with his brother's legacy. Ashton Kutcher Walden Schmidt

Aired between September 19, 2011, and May 14, 2012, Season 9 reboots the show's core premise. Two and a Half Men - Season 9 ...

A British woman who becomes Walden's primary love interest this season. Walden allows Alan Harper (Jon Cryer) and his