When Rebecca (Rachel Bloom) learns that Josh (Vincent Rodriguez III) and Valencia (guest star Gabrielle Ruiz) seem as happy as ever, she goes into a spiral and vows to make healthier choices. As a result, when nice guy Greg (Santino Fontana) asks her out on a date, she wonders if that is the path towards a happier life. Donna Lynne Champlin, Pete Gardner and Vella Lovell also star. Stuart McDonald directed the episode written by Erin Ehrlich (#104). Original airdate 11/2/2015.