Caroline Duffy (Lea Thompson from Back to the Future) is a cartoonist who puts out a syndicated comic strip about a single woman living in New York City. The series starts off with her looking for a new colorist. After quite a few bad interviews, she stumbles upon Richard (Malcolm Gets), a struggling artist with a bleak view on life.
Also included in Caroline's daily life is Annie (Amy Pietz), Caroline's across-the-hall neighbor and Del (Eric Lutes), Caroline's on-again, off-again boyfriend who also owns the greeting card company that uses Caroline's artwork.
Most episodes in the series are pretty self-contained, but the general progression of the season is maintained pretty well. For instance, Caroline and Del's relationship status is mentioned in pretty much every episode. Whether they have just broken up, just gotten back together again, or talking about the impending wedding (their relationship really is a roller coaster), you end up having a pretty good idea where the episode fits in the season, even if the main story has very little to do with that aspect.
As the season progresses, Richard starts to develop feelings for Caroline, and there are a couple of times when he comes close to telling her how he feels, but between Del's constant resurfacing and Richard's attachment to a girl that he really doesn't like, he feels like the time is never right to ask Caroline out.
Meanwhile, Annie, a dancer in the Broadway show Cats, has a constant stream of guys going in and out of her apartment, which acts as a pretty good contrast to Caroline's own unique relationship.
Oddly enough, the season has an extra episode after the cliffhanger. This episode, "Caroline and the Condom", definitely doesn't fit at the end of the season since some events obviously haven't happened yet. "Caroline and the Condom" actually acts as an odd clip show, where not only older episodes are shown, but scenes from an episode that was never actually made. Besides flashbacks to Richard's first day(s) on the job, Caroline and he talk about a time when Del and Caroline decided to take their newly-rekindled relationship slower than before. I'm not really sure why this episode was tacked onto the end of the season like this (thought it does look like it was originally aired several months after everything else), but the events of the second to last episode on the collection really throw the continuity of this episode off.
Anyway, though Caroline in the City: The First Season is scarce on special features (only offering TV commercials for each one), it is still good for anyone who remembers the series and wants to see how it started.
