Don't forget that how you say things is at least/probably more important than what is being said. Imagine "How Do I Look?" being said the way that Ginger on Gilligan's Island would say it(like in a throaty "I know I look good" kind of way). Some femme fatales might even say, "You can tell me how hot I look now" as they get ready to go out for the evening. Compliments can be requested - they may not given and it is some combintation of factors of style, frequency, intent, degree of neediness and reaction to rebuff that will determine how unattractive that asking really is.
This summer I have spent some time watching random teen/young adults interact at the pool, beach, whatever. There is a certain style to the way they deal with each other that has a degree of "Please notice me" that is not unappealing. Over time it could become burdensome but my overall feeling is "It depends".
