<jats:p> This article examines the middle-class work culture of Friends, reading it as a text imbued with both Restorative and Reflective Nostalgia. I argue that the “insulated precarity” of Friends’ protagonists, and their seeming nonchalance about work, marks out the show as a prime example of a Clinton-era “boom” text and as a one that struggles with rising anxiety inherent in neoliberalism. I focus on the role of Chandler Bing, who quits his nondescript office job to follow his dreams, before realizing he does not know what they are, and ends up in advertising. I argue that while Friends’ self-reflexive comic mode facilitates sympathetic treatment of Chandler as a “New Man,” his perpetual crisis of masculinity (his infertility, his periodic reliance on his wife’s income, and the constant questioning of his sexuality) is related to the lack of purpose in his career and, thus, the changing work culture that characterized the period. </jats:p>