Summary: Will happily takes Jack's son Elliot to his basketball game when Jack's job prevents him from doing so. While there, Elliot gets his first kiss from Nancy, and Will offers the teen some advice when he worries about what the kiss means. Jack returns early and when he hears about Elliot, he is outraged that Will gave his son advice, and upset that Will got to witness a "moment" in Elliot's life.

At the game, Will apologizes to Jack, telling him there will be lots of moments in Elliot's life that he'll get to witness. During the game, Elliot ends up losing it for his team and Will convinces Jack to comfort Elliot by telling him about the many times he's failed in life, thus getting a father-son moment of his own.

Meanwhile, Grace is excited to get a gig teaching students about interior design, but after they refuse to return because of how boring Grace was, she tells them she can get them to tour a celebrity's home. This involves Grace asking, or rather, threatening Karen to get her into one of the homes of her "connections", Katie Couric.

Karen agrees, but just as the students are ready to depart, Karen confesses to Grace that she doesn't know Katie Couric. The class leaves, and Grace realizes she shouldn't have tried to bribe them.

Did You Notice...
~Elliot's hair has gone back to it's original brown colour since he had it dyed blond in "Dyeing Is Easy, Comedy Is Hard".
~Nancy, the girl Elliot shares his first kiss with, last appeared in "Crouching Father, Hidden Husband" as the girl Elliot danced with. She has two moms, at least one of whom is gay.
~Submitted by Sebbie: The song Karen is singing in this episode when she's entering Grace's class is the same song she sings in "A Chorus Lie" before entering Will's room when Beverly Leslie interrupts her.
~Katie Couric, whom Karen claims to know, would later guest-star in the season 5 episode "Marry Me a Little".

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