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.

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

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.

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.

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

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 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 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.