Written by Michael Schur and directed by Greg Daniels, the episode first aired in the United States on February 9, 2006 on NBC.
The episode guest stars Craig Anton, Andy Buckley, Charles Esten, and Conan O'Brien as himself.
The series depicts the everyday lives of office employees in the Scranton, Pennsylvania branch of the fictional Dunder Mifflin Paper Company.
In this episode, Michael Scott (Steve Carell) travels to New York City to give a presentation, but carelessly tells everyone that he "hooked up" with Jan Levinson (Melora Hardin).
Craig, from the Albany branch, is completely unprepared for the meeting and attempts to cover for it by insinuating that Jan is giving Michael preferential treatment because of the supposed sexual encounter between them.
Phyllis Lapin is inundated with gifts from her boyfriend Bob Vance, while Pam is irritated with her fiancé Roy Anderson when the only thing he gives her for Valentine's Day is the promise of the "best sex of [her] life".
Jim Halpert is happy to be single on Valentine's Day, leaving him free to enjoy a poker night with friends.
He is forced to listen to Kelly Kapoor talk about how Ryan Howard kissed her during a bar meetup with friends.
The initial draft of the script in fact ended with a scene in which Jim steals Dwight's poem for Angela and gives it to Pam to lighten her mood after her disappointing Valentine's Day, but this scene was cut as the writers decided to emphasize that Jim is moving on from Pam and starting to enjoy a life independent of her.
He previously worked with Daniels on the writing staffs for Not Necessarily the News, Saturday Night Live and The Simpsons and the two also went to Harvard University together.
[6][7] Despite the brevity of his appearance, the shot required 15 takes due to difficulties getting the timing right and the frequency with which passers-by recognized O'Brien.
[9] When preparing to enter the Dunder Mifflin office for his presentation, Michael is seen sitting by the fountain in front of the tower at 1251 Sixth Avenue,[10] directly across the street from Rockefeller Center.
'"[15] Betsy Bozdech of DVD Journal called the episode "memorable" and noted that it illustrated Pam and Jim's relationship ebb and flow.
[16] Francis RizzoIII of DVD Talk declared that Ryan's statement about beginning to date Kelly before Valentine's Day was "one of the funniest lines in the entire season.