In the pilot episode, she has broken up with Del Cassidy (Eric Lutes), who quickly finds another date.

She hires Richard Karinsky (Malcolm Gets) to be her new colorist, and he pretends to be her new boyfriend during a dinner to prevent her from being embarrassed over Del's moving on.

Caroline's success as a cartoonist is displayed throughout the first season; her cartoon character gets a balloon in the Macy's Thanksgiving Day Parade, she has a park dedicated to her in her native Peshtigo, Wisconsin, and she even has an offer for a cereal brand.

[2] When she was a child, she drew violent pictures of her brother Chris, and after dropping out of college, she started doodling at a copywriting job.

Although Richard has kept his feelings secret, their friends Annie Spadaro (Amy Pietz) and Remo (Tom La Grua) figure out that he loves Caroline.

Caroline leaves a message on his answering machine telling him that she loves him, but Julia discovers it and erases it.

In the final episode, which ends on an unresolved cliffhanger, Annie and Del are now in a new relationship, while Caroline is about to marry another man—her childhood friend Randy—when Richard shows up at the wedding.

[9] Bonnie Timmons drew the illustrations and animations that are supposed to represent Caroline's eponymous in-show comic strip.

The same night, Lea Thompson appeared as Caroline Duffy (also never named as such but implied to be - and advertised as - her character) in the November 2, 1995, Friends episode "The One with the Baby on the Bus".