When we last left the cast, Richard (Malcolm Gets) finally decided to confess his love to Caroline (Lea Thompson). But since it was on the eve of her wedding with Del (Eric Lutes), he snuck her a note explaining his feelings and asking that she simply show up at Remo's (the local Italian restaurant) if she felt the same way. And if she didn't show up, then he would simply leave. In the standard sit-com manner, Caroline never sees the love note, and thus never goes to Remo's, even though Caroline and Del decided to call the wedding off at the last minute. Not realizing that Caroline never saw the note, he runs off to Paris in hopes of realizing his artistic dreams.
When the show starts back up, several months have passed and no one knows what happened to Richard, but since his funds have dried up, he finally decides to return to New York City where he can at least find a job at a local ice cream shop (much to his chagrin). Meanwhile, Caroline starts dating a young (very young) veterinarian, Joe (Mark Feuerstein). Eventually, Richard and Caroline meet up again and he takes up his old job of being her assistant, but Richard and the ever-present Joe butt heads constantly. And to make Richard's life just a bit more miserable, Annie (Amy Pietz), Caroline's neighbor, discovers Richard's letter and holds it over him as blackmail.
There are a couple of changes in this season of Caroline in the City. For one, Del decides to break away from his father's greeting card business and start his own, with his faithful roller-blade-clad assistant, Charlie (Andy Lauer), in tow of course. Now Del and Charlie work hard to keep their small Eagle Greeting Cards company afloat and slowly try to build a collection of cartoonists to produce products. The first client, of course, being Caroline.
Besides the slowly growing Eagle Greeting Cards, the season also focuses on Caroline and Joe's relationship, and of course Richard's feelings about the whole matter. Other over-arching themes include Annie's constant stream of lovers, her attempts to get better acting positions than her role on Cats and even an episode where she gets audited.
The season ends in a three-parter where Richard rediscovers a long-lost love, but since she is about to be wedded, Richard and Caroline act like they are already married. In a comedic twist, the two are forced to spend a night together. But when Richard and his ex finally start to get together, Caroline realizes that she just might have feelings for Richard. Let's just say, the season ends in a similar manner than the first, but with the tables slightly turned.
While generally predictable and almost all episodes ending with nothing really changed in the grand scheme of things, the show definitely hearks back to the comedy of the time, and quite frankly, the writing was just solid back then. Pretty much every episode left me laughing, and with very few pop-culture references, the show has aged well. Heck, even newer viewers will get a kick out of the various crazy relationships outlined in this series.
