Season 11: Episode 15 - Cab Fare and a Bottle of Penicillin

Cab Fare and a Bottle of Penicillin: When Lyndsey rejects Alan’s marriage proposal and ends their affair, he goes to Judith’s house to drown his sorrows. Their drinking leads to making out and the next morning, Alan wakes up in bed next to her, shocked to see the wedding ring he had meant for Lyndsey on Judith’s finger. Judith wakes up to tell him how happy she is and he loses the courage to renege on the engagement. Later, Alan and Walden have dinner at Judith's, and she proves to be the same domineering and bitter person she has always been. Walden urges Alan to tell her it was all a mistake, but Alan believes Judith is the best he can do. Refusing to let him settle, Walden tells Judith about Alan’s failed proposal to Lyndsey which causes Judith to end their engagement. Meanwhile, Jenny worries that Brooke is losing interest and decides to surprise her by setting up a kinky tableau at her apartment. Brooke walks in with her parents to see Jenny tied up to the bed. After the initial shock, Brooke reassures Jenny that she loves her.