The Winner S01 E04 What Happens in Albany, Stays in Albany

Alison can't join Josh on his trip to Albany for the State Spelling Bee, so she asks Glen to chaperone. Seeing that no one there knows the two, they decide to reinvent themselves to attract the ladies. Glen becomes airline pilot "Lance Manley" by wearing a toupee, and Josh pretends to be a cocky champion speller.