How to Be a Gentleman

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 meaningless fling, but Andrew struggles with not getting attached.

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.

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.

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