On "The Office", on what date do Kelly and Ryan finally hook up?

On “The Office,” Kelly and Ryan finally hook up on February 13th, the day before Valentine’s Day.

The date is established in the Season 2 episode “Valentine’s Day.” Kelly tells Jim that Ryan kissed her at a bar, while Ryan admits he regrets getting involved because it happened the night before Valentine’s Day. Kelly treats the encounter as the beginning of a serious romance, but Ryan sees it as a casual mistake.

Their mismatched expectations become the foundation of one of the show’s longest-running comic relationships. Kelly quickly imagines dating, marriage, and children, while Ryan repeatedly tries to keep the relationship casual or end it altogether. The pair’s on-again, off-again dynamic continues through later seasons, even after Ryan’s professional ambitions take him away from the Scranton branch.

A common mix-up is remembering the hookup as occurring on Valentine’s Day itself. The episode makes the timing clear: it happened on February 13, immediately before the holiday. The episode originally aired on February 9, 2006.