Liz runs into Dr. Baird in the lobby of their building and they awkwardly arrange a date for their first date. She doesn't realize until later that she has inadvertently insisted that it be on Saturday, Feb. 14th- Valentine's Day. Jack and Elisa share a moment (complete with delicious McFlurries) celebrating the fact that Jack's mother has recovered enough to move back to Florida. Jack proposes that they go on an elaborate date for Valentine's Day to celebrate even more, but Elisa tells him that they should go to church instead. Kenneth is smitten when he sees Jennifer, an attractive vision-impaired girl who has been newly hired at 30 Rock. He tries to help her get coffee, but is so taken with her radiance that he is struck mute and spills the coffee on his shoes instead.
Tracy sees that Kenneth is hot for the new girl so he plays cupid and helps him get close to her. Kenneth freezes up again, so Tracy talks for him and sets up a date between them for Valentine's night. He gets grizz and Dot.com to set up a table and in the hallway and serve dinner to Kenneth and Jennifer. He dines with them, providing the voice for Kenneth who still cant talk for himself around her.
Liz and Dr. Baird start their date with Liz cooking up a delicious cheese stew for them. She suffers an embarrassing wardrobe malfunction early-on, but Drew gallantly just tells her that her boob fell out without staring, so that seems to be the first hurdle successfully overcome. Unfortunately, there is much worse to come on their seemingly doomed first date. The stew disagrees with Liz and she is forced to visit the bathroom just as her desert begins to burn in the kitchen. Drew turns off the oven and opens the window to clear the smoke, but the draft from the window blows the bathroom door open, revealing Liz in a most "compromising position". She is mortified, but before the fallout from that incident can even be fully dealt with, Drew gets a call from his ex-wife informing him that she is dropping their daughter off with him tonight unexpectedly.
Jack and Elisa sit in a cavernous church for a beautiful and seemingly endless (at least to Jack) service. He phones his assistant during the lords prayer and tries to get him to hold his table at the exclusive restaurant he booked while still appearing to still recite the prayer as Elisa expects him to. His patience pays off and she agrees to leave.....as soon as they go to confession. Jack "used to be a Catholic" so he hasn't confessed ANYTHING for a very long time. He doesn't intend to start tonight, but as he gets going he suddenly cant stop admitting all the increasingly horrible things that he has done, seen, or been a part of. The Priest cannot deal with what Jack is telling him and runs from the booth leaving Elisa and the rest of the congregation staring at Jack. She is horribly embarrassed and storms out when Jack tries to get her to come with him to the restaurant. Jack eventually goes alone, but finds he cant enjoy the meal OR the $1000 desert without her, so he leaves and goes to McDonalds. Elisa meets him in line with a coupon for 2 for 1 McFlurries that she found in the church collection plate, so they are happily reunited regardless of whether by divine intervention (as she believes) or the workings of the free market economy (as he contends).
Kenneth and Jennifer's date goes well, and he eventually talks to her, admitting that he was too shy at first. She forgives him and praises his inner beauty before asking to feel his face so she can "see" him. Things then take an immediate turn as she suddenly backs away claiming that she has somewhere to be. Yes, Kenneth gets dissed hard by the hot blind girl and Tracy tries to call her on it, but she leaves anyways after concluding that she is much more attractive than he is.
Meanwhile, Liz and Drew's date continues to get worse and stranger as he asks her to come with him to the hospital to see his dying mother. As he leaves the room to check her chart, she tells Liz that she is actually Drew's Grandmother, rather than his mother, before dramatically dying with Liz by her side. Drew is devastated but then Liz takes the time to explain that his mother did not actually just die, so they get to spend more time together and even share their first kiss. As bizarre and truly horrible as most of the date was, it ended on a good note and that is enough for Liz to feel that Valentine's Day was a success.