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Louie gets roped into driving Sandy to the airport, where his car gets towed, making him late for his first meeting with his new supervisor (Gaffney).
When Louie tells Eddie how bad his new toupee looks, he removes it, and finds the experience so liberating that he decides to reveal another aspect of himself: his love of women's clothing.
After counselling a compulsive gambler, Louie finds the man's $5000 Lotto ticket in the trash. Meanwhile, Curt hopes for a reconciliation with Sandy.
Gallbladder trouble sends Louie to the hospital, but a row between Curt and Gretchen sends Louie, zonked on morphine, back out in search of them.
Louie debates the limits of doctor-patient confidentiality when Bob, who has admitted to embezzling $500,000, asks Gretchen for a date.