Jack is back in his box. Same cupcakes, same set of problems...and one new one: His new boss, Kris. Now Jack really has to work... on fine tuning the art of manipulation.

Gloria wants Jack to play the victim, Jack wants Gloria to tone down the sexuality and Baby wants milk.

Against Jack's better judgment, he visits Suzie at her home. Some co-workers just shouldn't get together outside of work.

Jack is ambushed at work when his mother, aunt and their friend Dawn come for a visit. Over a nice cup of coffee, they try to bond over pop culture. Will Jack be saved by the waiter?

Jack attempts to bond with his new boss Kris, and she is not having it. Where is Becca when he needs her? And will Jack have the balls to attempt said bonding?

Jack awaits a phone call from Drew and it becomes increasingly clear he has no clue how to date/be normal. After freaking out, he gets some misguided advice from his perpetually single girlfriends. Can Jack be smooth with his moves? Unlikely.

Jack and Drew go on their first date. Nervous laughter, sexual tension and really terrible jokes abound. Could Jack be happy?

It's been fun.