Ally has hallucinations with Barry Manilow. Richard assigns Ling to work with Jackson Duper, the firm's newest lawyer. When they meet, Ling discovers that Jackson slept with her in the past under a fake name. They have to handle a double case of a man who wants his marriage annulled because his wife is a nymphomaniac and cheated on him 106 times and is suing the minister for having a torrid affair with her. Between the unisex bathroom, Elaine's vibra and Melanie's Tourette, Jackson is going crazy with his new job and questions his future in the firm. Meanwhile, John proposes to Melanie. But Melanie doesn't want to be institutionalized (even if that institution is marriage)...

Elaine cheated on Mark and now she's trying by all means to find a way for him to forgive her. She even takes advice from Richard! But in the end she has a serious talk with Mark and she tells him she cheated because he never fully trusted her. They break up. Meanwhile, Jackson is assigned to do the pre-nup for a rich, fat and bald man. Ally puts Larry to defend to soon-to-be wife's interests, which leads into a more personal dissension between Larry and Jackson. And Ling takes the case of a man who's being sued by his own son because a blood clot has left him perpetually happy which is ruining the family business.

Ally and Victor return from their Bermuda trip. Ally feels their relationship is in crisis because they weren't able to connect without Maddie around. Victor is being sued by his former girlfriend for breach of contract. Ally discovers that Victor is a painter and never told her. She's angry, but not as angry as when she sees his painting of her with cellulite. Nelle and Wilson team up against a woman who was blackmailing their client in order not to come public with a tape of their lovemaking. Richard obsesses over Liza and has Claire do the talking for him through a hearing device, afraid she's going to turn him down - and even more afraid she'll say yes to him.