Barney seduces Marshall's law professor in hopes of getting her to grade more leniently. Lily takes a job at Ted's office, where she promptly steals to teach Ted's boss a lesson.

When Ted is constantly insulted by his former boss, who is now working for him on a project, he is told to fire the man, but he finds that a hard thing to do. Meanwhile, Barney offers Lily a lot of money to paint a nude portrait of him.

During a flashback, the gang wonders how the Ted, Robin and Barney love triangle will play out; Barney accepts challenges from Robin and Lily.