Episode 55 of "Ally McBeal"
s03e09 Out In The Cold

Ally befriends a homeless man who turns out to be a writer doing research on homelessness. They hit it off and just when Ally starts to think the man could be Mr. Right, she is stunned by what she finds about him. Meanwhile, Ling is arrested for running a brothel when one of her escorts has sex with a high school boy. Billy, still on his pro-testosterone kick, hires six of Ling's escorts to follow him around and be his "assistant." to add to the office disruption, Cage and Nelle have a post break-up argument.