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. Meanwhile, Mike and Janet seek help from Diane to prepare them for Mike's green card interview.
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.