Tied Up (after a line from the song below)
Starring: Zooey Deschanel and some dude, I don't know, she's pretty adorable.
Chicago: Two ad people, a man and a woman, a copywriter and an art director. They are teamed up but don't get along. They do terrible work together. There are funny scenes of them presenting work to unhappy clients, and their CD telling them that their work is terrible. There are humorous characters at the agency... the douchy account guy; the flaming, bitchy designer; the arrogant specialist writer; the invisible CD; the cool ACD that tries to help them. Eventually their work gets better and they start to get along, falling into the "partnership" relationship, but their passion for working together fizzles out and they get bored after a year or so. They have a one-nighter after a particularly boring late night of work while they're getting along very well. Soon after, they split up their partnership--she goes to live in San Fran with her boyfriend. He leaves his girlfriend and moves to NYC.
He is pale, sick and melancholic most of the time. She seems happy but develops weird habits. She moves to NYC with her boyfriend.
One day they are at a bar with coworkers from their respective ad agencies. They see each other and have a drink. Their work becomes terrible again, and they both realize its because they're in love with each other. She finds a funny and terribly cruel way to break up with her boyfriend that leaves him completely heartbroken and hopeless. It's clear that she has just now stopped loving him, and he never had a clue it was coming. We never learn much about him other than that he is a kind and decent guy who is committed to being with her.
It would be great to end the movie right there. Maybe close it with the sun shining behind Zooey's beautiful, innocent-looking, smiling face looking dreamily in love.