Caroline in the City (1995)

Season 2: Episode 17

When Caroline calls her out on always blowing her off for male dates, Annie makes a deal: they will go away together for a weekend skiing trip and ignore men. Naturally, both immediately spot exceptionally interesting men: an old school chum of Caroline's who confesses to having had a mutual crush, and for Annie a handsome tycoon. Meanwhile, Richard is hoping that his relationship with a fellow philosophy student won't remain Platonic, but the tryst he arranges in Caroline's apartment while she is away is invaded by Del and Charlie, who intend to make themselves at home to watch sports.