When Will's surrogate, Jenny (guest star Demi Lovato), tells Will their relationship needs boundaries, Will ropes newly-out Dr. DiLorenzo (guest star Chris Parnell) 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 (guest star Vanessa Bayer), and helping Jack build his confidence for a Broadway audition.
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