Despite his above-average intelligence, he's fairly self-destructive; he steals vehicles, engages in physical assaults, stalking, promiscuous sexual behavior, underage drinking, and he smokes cigarettes and marijuana. Lip has had a few love affairs through the series, including Karen Jackson and later Mandy Milkovich who applied to several colleges for Lip without his knowledge, winning him a full scholarship at one or more. After Lip found out that Mandy hit Karen with her car, causing Karen to become emotionally and mentally challenged, Lip dumped her.