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.'
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 teaches Andrew that it is possible to have a one night stand. However, when Andrew finds a girl to have a one night stand with, he ends up falling for her. Andrew, being the consummate gentleman, has a tough time with the idea of a one night stand. But Bert is trying to get him to work on his self esteem and to loosen up a bit. When Andrew surprises Bert by hitting successfully on a pretty cellist at a bar, Bert warns him not to fall in love! When Andrew comes home the next morning, he announces that he and the cellist are going to have little baby cellists. Bert spend the rest of the episode trying to talk Bert out of calling the girl. At the end of the episode, the cellist dumps Andrew. Andrew realizes that Bert was right.
Andrew is invited to his ex-fiancée’s wedding and hesitates on attending but Bert encourages him to get closure. Although when Bert discovers that Andrew’s ex met her new husband while dating Andrew, Bert encourages him to take this opportunity for confrontation rather than closure. At the start of the show Andrew and Mike are grocery shopping and they run into Lauren -- Andrew's ex fiancé who shattered his heart. Lauren extends an invitation to Andrew to her wedding. He tells Bert there is no way he will go, but Bert talks him into going so that he can move on with his own life. In the mean time Andrew finds out that Janet, Mike and his mother are all attending the wedding. Andrew also finds out that Bert RSVPd for Andrew to attend plus one. Bert is going to be his date. At the wedding Janet and Mike find out that Lauren Cheated on Andrew -- there are photos of her first date on the tables -- and the date took place before Andrew and she broke up! They all try to hide the photos form Andrew, but he ends up figuring it out, and handles it like a real gentleman.
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.
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-fiance, 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.