30 Rock
Liz Lemon, the head writer for a late-night TV variety show in New York, tries to juggle all the egos around her while chasing her own dream.

Season 4 · Episode 13 ·
Anna Howard Shaw Day
Liz schedules a root canal to avoid feeling lonely on Valentine's Day; Jack woos an attractive and successful TV host; Jenna's stalker loses interest.
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Episode 13 of season 4 of 30 Rock: “Anna Howard Shaw Day”. Aired 2010-02-11. Watch it online free on ZapFlix.