Tucker Max is an asshole but the kind of asshole that all of his asshole friends love because his antics distract them from the thinning hair and gentle mediocrity that characterize their post-college years.
Most Tucker Max stories involve him doing or saying crazy/offensive things, getting into trouble for them, and then going home with one of those girls who, when a guy says something sort of awful to her, hits him on the shoulder and says "you asshole" but also smiles and sticks to him like glue for the rest of the night. My dad was nice to me, so I don't have this reaction, but I guess it takes all kinds.
Invariably in Tucker's stories, someone gets pissed off and says his jokes aren't funny, and if that someone is a woman, she's dismissed as ugly and/or fat and therefore too bitter and angry to get the joke, while if that someone is a man, he's dismissed as being a meathead and therefore not cool or smart enough to get the joke. If you are confused by this last, let me clear it up for you: Tucker Max is unaware that he is the definition of a hazey, rapey, fratty meathead.