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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 Carlson as etiquette columnist, is told to adapt to a much sexier style, for the new image of the magazine, he hires his old high school bully Bert Lansing to try to help him to be more modern and sexy.