St. Valentine's Day

Season 3, Episode 11, Aired
EDIT

Episode Recap

This week, 30 Rock experiences very strange Valentine's Day dates.

Liz and Dr. Drew Baird have their first date on Valentine's. The date starts with Liz's boob falling out of her blouse while she tells Drew how she was born on the Maryland-Pennsylvania border. When she is relieving herself of the cheddar cheese stew she cooked for their date, the draft blows the bathroom door open while she's on the toilet.

The date keeps getting worse – Drew's ex-wife drops off their daughter on his date. The tween loves to drink and collect colored bracelets for doing certain things on the bus. Her visit is interrupted by the news that Drew's mother is dying. While acknowledging it is "too soon," she ends up going to the hospital to his mother's bedside. When Drew briefly leaves the room, his mother tells Liz the deepest, darkest secret about Drew and passes away. After the most awkward and inappropriate night, they still decide to move forward.

Jack, too, suffers through his Valentine's Day. Jack is forced by Elisa to go to church instead of restaurant, Plunder that serves a $1,000 dessert. When the church service runs late, Jack contorts the Lord's Prayer to call his assistant to delay the reservation. Before they leave, he is dragged into confession where he drives the priest away with his unending list of sins. The priest runs away from confession saying, "Harvard didn't prepare me for this."

Elisa and Jack break up but quickly reunite when Elisa sees a McFlurry coupon in a collection plate. She goes to McDonald's to use the McFlurry coupon and finds Jack there as well. She sees it as a sign that they belong together while Jack sees it as the successful work of capitalism.

Meanwhile, Kenneth has fallen hard for a blind intern. He is so smitten that he cannot talk to her. Tracy decides to step in and pretend to be Kenneth with a few yes-indeedys. Tracy even helps Kenneth fake a fancy Valentine's Day date on the TGS set. In the end, Kenneth confesses that Tracy has been speaking for him. When the smitten Jennifer goes to feel Kenneth's face, his lack of a chin turns her off and she runs away.