Episode 91 of "Ally McBeal"
s05e01 Friends and Lovers

It's a new year at the firm, which means changes - big changes! Still getting over Larry and renewing her faith in love, Ally decides to start fresh and let nothing get in her way. That is until she barrels into a woman on the street with her Razor Scooter. She runs into Jenny Shaw (Julianne Nicholson) and instantly bonds with this new broken-hearted stranger. In the time it takes to walk the rest of the way to the office, Ally finds out that Jenny's best friend is her ex-boyfriend, former co-worker and that Jenny is a lawyer without a firm and with a class action lawsuit housing 72,000 plaintiffs! Ally brings Jenny into the firm and announces that she's hiring her. Of course Richard is surprised because only he has hiring authority. He then lets Ally know that he already hired the latest addition to the firm: Jenny's ex-boyfriend Glenn Foy (James Marsden). Ally argues that he should also keep Jenny however because of her 72,000 plaintiff suit. Dollar signs light up in Richard's head and he welcomes her aboard. Later that evening, Jenny and Ally talk about whether friends can be lovers or lovers can be friends. John overhears part of the conversation as Ally tells Jenny that she loves John. But he doesn't hear the "just as friends" part. In court the next day, Jenny fights to keep the lawsuit against the phone companies alive. She argues her point against her old firm who now represents the phone companies. Glenn's best friend, Raymond Millbury (Josh Hopkins), represents Jenny's old firm but loses the first part of the case as the judge rules in favor of the plaintiffs as an actual class. Meanwhile, John freaks out about the (false) newfound information of Ally loving him. He tells Richard, soliciting advice. Richard tells him to declare himself by giving her signals that would allow her to come to him. John gradually begins making his move, but Ally cluelessly ignores his feeble attempts at flirtation. When he finally tells her how he feels, Ally takes it as a joke and storms off perturbed. At the bar that night, Jon finally works up the courage to tell Ally how he truly feels about her. Just as he's about to drop the bomb, Ally remarks how glad she is that she and John have such a great "plutonic" relationship. John leaves his courage at that and decides to hold off on his feelings for another day while at the same time Ally begins thinking that she may be harboring feelings of her own for the firm's hottest new addition - Glenn.