Following a woman around, listing off characteristics about her and trying to guess things about her, loudly, is assanine. It is not flattering, it is not cool, it is not funny, and it sure as hell is not going to earn you points with her.
"Look, there, no, her over there. The hot one with the ponytail. Yeah, I see her walking along here every week. I know it's her because she always wears the same coat and pants" (Which I don't, I just happen to prefer dark denim, and it's been cold so I wear my parka most days.) "She's got to be somewhere between 18 and 19. I'm betting... she's got to be 17 3/4. Don't worry man, she'll be 19 soon. *lecherous chuckle" (I'm 23.) "But she's definitely a sophomore, definitely man, so you're good." (I'm a 5th year "super-senior.") "That hair is probably dyed, too." (No, I'm just the first natural blond you've seen this side of the Atlantic.) "Yeah, she's DEFINITELY possible. Dude, totally! *laughter* *mutter mutter* ask her *mutter mutter* See ya later, man!" (No. Hell fucking no. I am not even a remote possibility for you assholes.)
Seriously? Do parents teach their children no manners anymore? Thank goodness I'm not looking for a boyfriend right now, because I might be tempted to stab my eyes out in frustration at the 3rd grade social tactics of the testosterone-drenched sex.