Conrad Bloom is the ultimate nice guy. As a young advertising copywriter working in the Big Apple, Conrad is constantly putting his professional and personal dreams on hold. In the opener, Conrad thinks he may have found his one true love in Allison, but keeps breaking dates with her to (1) be a dance partner for his mom; (2) bail his activist-sister Nina out of jail; (3) baby-sit for his art director, Shelley; (4) comfort his ex-girlfriend Molly; and (5) save the job of a brain-fried co-worker.

The ad team scrambles to find a celebrity named Jerry to promote a client's potato chips after Shelley lies about landing Jerry Seinfeld. Also, Conrad tries to prove to Nina that their mother loves them equally.

Conrad finds his friendship with Molly threatened by a jealous new boyfriend. Meanwhile, he tries to persuade his sister and lonely mother to live together.

A breast pump wreaks havoc for Conrad who falls for a woman with great Yankees seats---then he sees her tattoo. Meanwhile, Florie meets an old foe.

Conrad hopes to impress his boss Faye by showing up at her party in a Titanic outfit with Molly.