Guest Stars Adam LeFevre as Captain Brian Morris Dani Deetté as Rori Barnhill Brooke Bloom as Fiona Layla Felder as Emma Hughes Leslie Fray as Melanie Phillip James Brannon as Brian De'Adre Aziza as Mrs. Hughes Gregg Edelman as Philosophy Professor Brian Hutchison as Mitch Russo Garrett Coffey as Younger Jamie Ryan Stiffelman as Younger Nick Co Starring Amelia Windom as Margaret Ryan McCarthy as Peter Alexa Shae Niziak as Courtney Kerry McGann as Sandy