Stalking, on account of technological development, has become a modern crime. The term itself is very hard to define. It is characterized by the repetition of certain acts which otherwise may be deemed as normal (phone calls). This paper was set to examine stalking or stalking-like behaviour which is present in American popular culture but is not regarded as such, or is regarded as more benign than it really is. Ten examples were given, which were further divided into two groups: comedic representation of stalking in American popular culture and romanticized representation of stalking in American popular culture. Throughout these examples, one can notice differences between the two groups; stalking which is represented humorously is more explicit, in contrast to romanticized representation of this behaviour. Moreover, females are rarely represented in the same comedic and romanticized manner in these contexts as men are. The given notion can be explained by the centuries of patriarchy and the established gender roles which deem women to an inferior position in regard to men. The change of the established patterns is difficult, but is necessary.