In "Nangnangnangnang", after Jenny appears on Walden's doorstep looking for her uncle, Walden took Jenny up to his (previously Charlie's) room. To connect with the last pieces of her father. When Evelyn tells Jenny to move in with her, Walden is relieved. However, by the end of the episode, he changes his mind, allowing Jenny to stay in his house.
In "I Think I Banged Lucille Ball", Walden tells Alan Jenny has to move out so he can put in a home gym. When Jenny, Evelyn and Marty come for dinner and get high, Walden tells Jenny that she is becoming a part of his family, and allows her to move back in.
In "Clank, Clank, Drunken Skank", Walden starts partying with Jenny and her friends, eventually leading up to an orgy (which included Walden, Jenny, Jenny's friends, Berta and James Franco).
In "Alan Harper, Pleasing Women Since 2003", Walden tells Jenny to take acting lessons. But Jenny refused. Later Jenny told him like she was very upset of her life. Ending with 'and that's why I don't need acting lessons', showing she wasn't upset at all. Leading Walden to give up on her.