Caroline hires Richard as the new colorist for her comic strip. Annie tries throwing fruit out Caroline's window to hit a date for Caroline.
Richard has to tell Caroline that he's been mugged. The mugger also took Caroline's drawings that are due the next day, forcing them to rush new ones and Caroline cancelling a date with Del.
Caroline and Annie convince a gallery owner they meet at Remo's to look at Richard's paintings. The owner agrees to show Richard's work. Unknown to Richard, it's a gallery for gay artists.
When Caroline gets her back injured, and Annie gives her some "better" painkillers than the doctors, Del and Richard rush to create a Caroline in the City cartoon strip so that Caroline doesn't miss her deadline and a Cathy strip replaces it.
In order to claim money she did not receive while making an ATM withdrawal, the bank manager must watch a video of Caroline making the withdrawal. This sends Caroline into a panic as, unaware she was being recorded, she picked her nose.
Del gets delayed when he and Caroline are to meet Del's parents at Remo's, leaving Caroline to her own devices. Annie disrupts Richard's plan to do nothing for his 30th birthday.
When Del tries to get out of going to the opera with Caroline, she goes with an old high school classmate who happens to be richa and successful.
Caroline's cartoon character gets a balloon in the Thanksgiving Day parade. It gets set loose, in the process hurting Florence Henderson who is the parade marshal.
When Caroline's apartment is burglarized, Caroline suspects Annie's new boyfriend, recently released from prison.
Annie attempts to help Richard end things with Shelly, while Del and Caroline reconsider their relationship when vacation plans bring up issues.
Having recently split up, Caroline is unsure what to do when Del gives her a gift that she thinks is very expensive. Meanwhile Richard is commissioned to do a nude portrait of a woman who turns out to have ties with the mob.
Caroline gets set up by Richard on a date with a man who could get Richard a well-paying mural job. But Richard later discovers the man is married.
Caroline's hometown has a ceremony in her honor. Caroline arrives along with Richard to find things haven't changed much, as her brother continues to upstage her at every turn. Annie thinks her understudy is trying to steal her place in Cats.
Caroline buys a new work desk that is difficult to get into the apartment. She finds an old watch in a stuck drawer and looks for the original owners whose names are on the inscription. Del goes to the funeral of an employee that Charlie tells him was embezzling from him.
Caroline meets a man who turns out to be overly paranoid. Del sets himself and Richard up on a double date with two models.
Richard learns that Del proposed to Caroline. Thinking he'll just be in the way, Richard starts looking for a new job. Annie and Remo try to convince Caroline that she's oblivious of Richard's feelings for her.
Del feels inadequate when he meets a particularly chiseled ex-boyfriend of Caroline's. Caroline and Richard are hired to paint a mural in the room of a spoiled little boy.
Del and Caroline go on a vacation to Del's cabin, only to find his ex-wife staying there with her latest partner. Annie has family troubles when Richard convinces her brother to quit the family business.
Caroline, Richard, and Annie are extras in a movie filming outside their building. Del's Porsche gets towed, only for someone else to pick the car up as theirs.
Caroline's cartoon character is offered to be on a cereal box, but Caroline can't get past the shape of the cereal looking too much like a female body part. Del asks Annie to teach him how to dance.
Richard's mother makes a surprise visit, continuing a string of claims that she knows all kinds of well-known people and irritating Richard in front of Caroline.
Caroline doesn't feel like Annie is taking her position as maid of honor seriously. Del is having difficulty finding ushers for the wedding.
The wedding is threatened by dreams of Richard, a last-minute change to an inexperienced priest, and more.
Caroline has flashbacks of Richard's first day working with her. (This episode was aired outside of the normal season airings, and out of order. It makes more sense viewed just after episode 14, "Caroline and the Watch".)
