When Andrew is given the opportunity to ask out a model, he is forced to realize that even a gentleman can be shallow about some things. Meanwhile, Bert discovers that events from his past may be the reason for his commitment issues.

When Andrew skips Thanksgiving dinner with his family to rekindle a relationship with his ex-fiancÄ-e, Bert reminds him of his newfound "manhood" by showing him the error of his ways.

When Andrew is left picking up Jerry's slack at work, he asks Bert to come on board to serve as his new life coach, but quickly realizes he might have made a serious mistake.

When Andrew refuses to make a move on his attractive new assistant, Bert teaches him a lesson by going out with her.

When Bert sends out angry emails that Andrew drafted but never sent, Andrew scrambles to make things right with the recipients. Meanwhile, Andrew turns the tables on Bert and forces him to stop filing away his emotions when his judgmental father shows up.

Andrew and Bert each have their own unique relationship with the same woman, but Andrew starts to feel short-changed when she spends every night in Bert's room.

Andrew attends his ex-fiancée's wedding and learns that she cheated on him with the groom while they were still together.

Bert instructs Andrew on how to enjoy a one-night fling without getting too attached emotionally, while Diane agrees to prep Mike for his green-card interview.

When an etiquette columnist is told to adapt to the modern and sexy style of his magazine, he turns to his former high-school bully for balance.