Woody falls for a new tenant, a divorceé with two children. He worries over the difference in their ages. Chuck even asks Ellenhorn if he has any advice. The situation comes to a head when Woody's parents unexpectedly drop in on a romantic restaurant dinner.
Chuck tries his luck as a model for an advertisement being shot by Jack Ellenhorn, but proves to be unmanageable, driving Jack to inadvertently hire a hit man. In his remorse, he confesses to Woody and Chuck that he can't even remember what the man looked like, putting Chuck into a panic.
Woody and Chuck are determined to not end up on a weekend night with their old friends at the same dull party destination, so they go looking for girls. They find some tourists at a movie theatre but they go off with some guys leaving the show, then at an arcade, they find some receptive girls whose tough boyfriends soon show up.
While waiting for a coal shipment Woody and Chuck find the building's original blueprints, and a heretofore unknown room is shown. They try to locate it in the girl's apartment, but break into Ellenhorn's dark room. Later the find the room, one that Woody's Uncle used as a secret sanctuary.
An exciting young secretary is Woody's latest heartthrob, but he's consumed with jealousy when she seems to be interested in her boss, a rich playboy publisher who's in his forties. This is considered unseemly great age to Woody, who challenges him to a showdown.
Boasting that tickets to the big game can be had, Chuck forces Woody to beg for them from a star player on the visiting team. They went to high school together in Ohio, but the egomaniac footballer has no recollection of him, and the boys must wait in a long line at the box office.
When Woody and Chuck can't make the rent on the beach house, they con Ellenhorn into going in with the promise of a quiet, peaceful stay with only the three of them. But before they realize it, three beautiful beach bunnies and then a bunch of freeloading musicians insinuate themselves into the crowded shack. When Ellenhorn arrives, they try to hide their new roommates.
In the park, Woody and Chuck mistake a mugger for a victim, and try to fight a cop trying to arrest the crook. They are set free after a trial, but the holdup man, now on the lam, comes to the apartment and has the hapless duo, and soon, one by one, all their visitors, held at gunpoint.
Chuck is recruited by the police to talk his old street gang, "The Gladiators", out of engaging in a ramble. He gets too involved and another former gang member that's made a successful career in crime with a bookie joint fronting as a laundry, must intervene.
Woody and Chuck have an unexpected new tenant, a young blonde that cons them into staying rent free in Ellenhorn's apartment while he's on a picture assignment.. But he gets back sooner than the boys expect, so they talk him into moving in with them. Unfortunately, they are incompatible room mates with the fussy photographer.
A play that Woody has written is going to be produced, but not on a Broadway stage, it's women's club in Garden City. They prove to be hopelessly inept and frustrating, but the play is obtuse and overly arty anyway, so Chuck tries to add some low comedy.
The boys need money in a hurry to rent tuxedos for Ellenhorn's gallery show, so they go to a scientific research facility. There they get paid to participate in grueling food and sleep deprivation experiments. After they're over, they show up ill-suited to help host the event.
Woody and Chuck's new tenant is Emile Kucheck, a famous high-wire acrobat from Czechoslovakia. While he's away at a performance upstate, the boys must look after Mrs. Kucheck, who's very pregnant, and doesn't speak English. Problems mount when they must take her to the hospital when the delivery becomes imminent.
Ellenhorn warily accepts to take woody's visiting Aunt on a blind date, but he didn't realize she'd be pretty much his polar opposite. He's a high-strung, whiny introvert, and she's a brash, loudmouthed army sergeant who emasculates him on a date, and starts, and wins a fight in a restaurant.