Liz spends more time with her boyfriend Drew (Jon Hamm) and finds that his handsomeness allows him to bypass many of the usual frustrations of daily life. Jack must find a way to convince Tracy to stay on at TGS after his contract expires and Jenna considers a new hairstyle to attract public attention.

Excitement for TGS's 50th show is quickly replaced by concern about company budget cuts. When Jack is forced to hand out pink slips, Liz does some personal bartering to save her staff.