At the bar, Sam bumps into Jolie, a girl he previously ditched on their third date. Sam's plan to reconnect with Jolie is hampered by a series of curve balls thrown by his boss.

A last-minute brainstorming meeting forces Sam to bail on his date with Piper and rescue her from sleazy Derek.

To ramp up marketing to families, Russ decides that the airline needs a family-friendly icon. Sam submits a really great idea from Darcy, however Russ mistakenly uses a doodle drawn by Sully. The result is very "Sully-like."

Sam feels that he is one of the boys when Russ invites him to a business lunch with the heads of the other airlines. However the experience is not without trouble, as Sam makes a simple donation to a charity sponsored by "The Dutch", which causes him much more than he bargained for.