Milo and Robyn go out with different partners to the same restaurant where they had their disastrous date. Sam wants more money from Jack.

Sam directs a commercial based on the disastrous date between Robyn and Milo. Robyn starts dating the "fake Milo".

Sam tries to end his losing streak at an awards ceremony. Jack receives a lifetime achievement award, while Robyn reflects on her lack of life experiences.

Milo pretends that he is gay in order to win a potential client. Robyn tries to impress an old girlfriend by pretending that Sam is her rich fiancee.

Milo helps Sam get Sam's uncle's watch back from a crazy ex-girlfriend.

Milo finds out that his former girlfriend is getting married.

Robyn and Milo tries to keep Sam from finding out which guy in the office her friend really likes.

Robyn finds out that her mother is dating her high school boyfriend.

Milo dates a beautiful woman and her alleged twin, who are both auditioning for a commercial.

Milo is set up on a blind date with Robyn. The date doesn't go well, but the next day Milo finds out that Robyn is his new boss.