Synopsis: That's Funny, Isn't It?
Will is a young, struggling, standup comic, who shares a low rent apartment with his girlfriend, Grace, and a self-employed realtor, Chuck. The film opens with voiceover from his standup routine as the camera tracks Grace serving customers at an outdoor café where she waitresses. Grace is burnt out from the job, burnt out from life, can't pay her share of the rent, and she's missed her period & thinks she might be pregnant. After a tedious shift, she returns to the apartment only to be hassled by Chuck about the rent money (what's worse: she hasn't got it). Chuck is a penny-pincher (hence the hassling), something of a nerd (he wears a tie in his home office to 'dress for success'), and has a sort of socially maladroit pathetic charm to him.
When Will comes home later that day, Grace tells him Chuck's been pestering her for the rent. Will, who just wants the three of them to get along, says he'll talk to Chuck — he suggests, in fact, that they bring Chuck along to the beach outing they had planned for the following day. After all, says Will, Chuck really could use some fresh air. Then Grace tells Will she thinks she's pregnant. Will asks her to marry him. It's unclear whether he's serious or mocking.
At the beach the next day, the three talk, but futilely. None of them can connect with the others. It also becomes apparent that Will is more than simply struggling: he is troubled, and may be suicidal. The film reinforces this through interspersed snippets from Will's standup routine (his comedy largely draws on personal experience and the snippets thus provide back-story and also serve as oblique commentary on the present action). On the car ride home from the beach, all three have succumbed to silent resignation.
But life inexorably plods along. The next day, Will is back doing standup. Chuck is closing a real estate deal. Grace is back waitressing. As the film ends, Grace calls Will to say she wants to get married. By all objective measures, it appears a happy ending. The tone of the film suggests it's anything but.