Liz unintentionally insists her and Drew (Jon Hamm) have their first official date on Valentine's Day. Jack goes to church with girlfriend Elisa and Tracy helps Kenneth win the affection of a new staffer.

Liz befriends a pregnant teen in an attempt to adopt her baby. Jenna vies for more attention but Kenneth's plan to combine her birthday party with one for Tracy derails her efforts. Jack goes out with the guys and bonds with Frank over daddy issues.