When Walden's girlfriend Kate expresses her frustration at her lack of career advancement, Walden tries to help her without blowing his cover as Sam Wilson by giving Alan 100k to invest in her fashion designs. After Kate thanks Walden for facilitating the investment and being a genuine guy, Walden feels guilty and experiences erectile dysfunction. Walden tells Alan about being stressed over lying to Kate and he suggests Walden tell her the truth or take erectile dysfunction pills. Walden chooses the quick fix of taking the pills, but Kate is too busy preparing for New York Fashion Week to spend any time with him. Kate leaves for New York and Alan finds a dejected Walden holed up in Kate's apartment.