If you don't know anything about Caroline in the City TV series that was inspiration for this game you should take a look at Caroline in the City or Characters pages to get a graps of the basics, although no in-depth knowledge of the series is required to play the game.
The plot of the game is rather simple - New York based, but Wisconsin-born, cartoonist Caroline Duffy is about to get married in two weeks. But this morning something happened to you - you woke up in the morning and realized that in fact you are in love with her. What is more you realized this is your last chance to tell her how you feel before you will lose her forever, before she will get married to Tim Walters, a wealthy businessman from Atlanta.
Tim is a bit of a jerk, so you are sure you're doing the right thing trying to stop Caroline from marrying him. Of course it wouldn't be right to just tell her how you feel on the phone, so you've decided to pay her a visit... And so your travel begins.