Celeste (Rashida Jones) and Jesse (Andy Samberg) are best friends who start dating in high school and eventually marry young. Their relationship is shown in a photo montage; the montage ends with Celeste walking away from Jesse during a party.
Celeste and Jesse still get along well. Celeste is a successful trend analyzer and runs her own media company with her partner, Scott (Elijah Wood). Celeste's media company has just signed Riley Banks (Emma Roberts), a teen pop-star whom Celeste does not respect and had openly bashed during a previous television interview. Jesse is an unemployed artist in no hurry to find a job.