Committed to becoming a father on his own, Will meets a potential surrogate with stellar reviews, but her lifestyle choices give him doubts. In order to gain entry to AnnieCon, Grace pretends to be a formerly famous Annie.

When Larry warns Will and Grace about the difficult entry process into the elite school they both want their kids to go to, they set out to prove that their child would be the better candidate. While helping Jenny with her ASMR livestream, Jack unwittingly creates problems between Karen and her “booty buddy,” Luke.

Jack helps Karen sneak into the manse to retrieve her coveted ring, but they're shocked to find it on the hand of Stan's new girlfriend, Val. While hosting Will's surrogate, Jenny, for the weekend, Will and Grace become the old folks they swore they'd never become.

When Will's surrogate, Jenny, tells Will their relationship needs boundaries, Will ropes newly-out Dr. DiLorenzo into going on a fake date so he can spy on Jenny. Unsure if having a boy or girl is more difficult, Grace struggles with popping her gender reveal balloon. During her baseball team's championship game, Karen is torn between celebrating with Friday, and helping Jack build his confidence for a Broadway audition.