When Andrew is given the opportunity to ask out a model, he is forced to realize even a gentleman can be shallow about some things. Meanwhile, Bert finds out 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-fiancee, 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 serve as Jerry's 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.
Andrew and Bert each have their own relationship with the same woman, but Andrew starts to feel short-changed that she spends every night in Bert's room.
Bert talks Andrew into attending his ex-fiancee's wedding for closure, but when he discovers his ex met her husband while she and Andrew were still together, Andrew must decide how to confront her.
Bert tries to teach Andrew how to have a meaningless fling, but Andrew struggles with not getting attached.
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.
How To Be A Gentleman, inspired by the book of the same name, is a comedy about the unlikely friendship between a traditional, refined writer and an unrefined personal trainer. Andrew Carlson (David Hornsby) is an etiquette columnist whose devotion to ideals from a more civilized time has lead to a life detached from modern society. When Andrew's editor, Jerry (David Foley), tells him to put a modern, sexy twist on his column or be fired, he hires Bert Lansing (Kevin Dillon), a reformed 'bad boy' from Andrew's past, as a life coach in the hopes of learning to be less 'gentle man' and more 'real man.'