When etiquette columnist Andrew Carlson is told he must adapt to the new, sexier style of his magazine, he hires his old high school bully Bert Lansing to help him become a modern man.

Bert tries to teach Andrew, how to have a one-night stand, but Andrew struggles with not getting his hopes up. Meanwhile, Mike and Janet get help from Diane preparing for Mike's green card interview.

Bert convince Andrew to attend his ex-fiancee's wedding for closure, but when he learns that his ex cheated on him, Andrew has to decide how to confront her.

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-fiancée, 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.