The first episode opens with Caroline placing an ad for a new colorist, her last one having moved to Chicago and gotten married. When the applicants come they include "Munro" and a woman so obsessed with Caroline's strip she wants to be Caroline. When the second woman leaves Annie, the neighbor, greets Caroline and says goodbye to the man she'd spent the night with.
Caroline tells Annie she and Del have broken up and Annie doesn't understand why. Caroline says she's going to take a break from men when the third applicant, Richard Karinsky, buzzes her door. Caroline tells Annie that she and Del have a meeting later and Annie says she shouldn't have dated a co worker. When Richard appears it's obvious he doesn't want to take the job, telling her it's only for money and he can't make any as an artist. He hates Caroline's cat Salty and when Caroline says she'll call him back he doesn't believe her. He makes a fuss of telling her his phone will be cut off and he can't pay rent so he gets the job. He instantly leaves for lunch, saying he doesn't start before 10am and takes an hour and a half for a break.
At Del's office at his greeting card company Caroline is nervous but tries to show him her drawings when Del asks her why they broke up. She tells him he can't commit because he's had two ex wives. The go-for Charlie comes in to tell Del about his ideas for cards for women's menopause and to announce coming out "good for gays, good for debutantes" and leaves. Del says he wants to be friends but when Caroline suggests a movie he says eh has a date. Caroline is annoyed he's taking her to their favorite restaurant so says she's going there too.
Caroline tries to get a date but no one is available. Although Annie and Richard don't hit it off Annie suggests Caroline take him but Caroline says no. Richard only listens to Caroline's story when he gets a raise and then leaves, but Caroline makes him take the drawings they hadn't finished and gives him a key. Annie throws fruit out the window and Caroline asks a guy out on a date.
At the restaurant Remo's, the owner had thought both del and Caroline had booked a table so canceled Caroline's but is thrilled when she tells him they broke up. Caroline arrives alone and picks out a table in the middle of the room. Del and his date appear and as she is alone Caroline insults Del's date as she's much younger than him.
Richard returns to Caroline's apartment and hears her date cancel and his wife calling him away so goes to the restaurant to tell her. When Del comes to say hello Richard pretends to be the date and kisses Caroline, telling Del he's a surgeon. Del returns to his seat and Richard stays but is still on the clock.
After their dinner Richard and Caroline go back to her flat and as they are going to leave Del arrives, saying he was only coming to return his key. When he uses the key to show off Richard holds the one Caroline gave him up too and gives one last crack about his wealth before leaving. Caroline admits to Del who Richard is and despite Del's pleads says she just wants to be friends. Del kisses her inside her apartment and the lights fade out, showing Richard walking home alone.
