Rose man - spending money out-of-line with the level of connection. Absence of sense of perspective is very scary.
Threats are scary ("she's got a boyfriend", "thats ok I know how to beat people up".). Note also displays absence of normal sense of perspective.
Hard to tell who's a dangerous whacko and who's just confused about the normal social graces and limits. Sadly in US judicial system, the mis-judgement on a woman's part is still too often used to turn her into the criminal instead of the victim. Its improved over past 30 years, but still has a long long way to go.
So, I think we have to expect public figures to be wary. I'd describe "the line" as being comments that imply a greater knowledge of/connection with the person than you really have, or comments that objectify the person rather than deal with the person as a human individual.
The DJ is the DJ - have you had a personal conversation or just watched via the webcam? Is she a person or a sex-object? IMHO, complimenting the person on her looks is easily distinguished from complimenting "the babe" on her looks.
Whew, Im on a rant. Time for meds. Dont have any of my own. Who will share???
Altoid - curiously strong.