Sheldon Wickens is one of Theodore's copier service clients who's been asking him out on a date for years. Theodore thinks he's hot but always blows him off, thinking there's no way Sheldon would be interested in a blue-collar guy who's a little overweight. Plus, he's tired of one-night stands.
But things take an interesting turn when Sheldon signs a lease in the same apartment complex where Theodore lives. When Henry sees the simmering attraction between them, he decides to play Cupid at the end of summer lounge party.
Will Theodore take a chance on something new, despite the bumbling efforts of his best friend, or remain unrequited forever?