For those of you who don't know, Ugly Duckling Syndrome is where a really beautiful girl doesn't know she is beautiful because she was an unattrative as a child but blossomed into a beautiful young woman. This is a serious problem. These "ugly ducklings" are often very nice girls because they were ugly as kids, not the attractive kids who made fun of the ugly ones. I know this girl who is an ugly duckling. She's 18 and definitely a ten with a very nice body that's filled out quite nicely in all the right places. But she keeps dating these ass ugly weird looking guys. I'm an attractive guy btw, or so I've been told, and want to get her to go out with me but my friend told me since she was an ugly duckling there is a good chance she is intimidated by me because she doesn't think she is pretty. What is a good tactful way to tell a girl she has Ugly Duckling Syndrome and to tell her to stop dating these ugly guys because she could pretty much get any guy she wanted. I don't know why but this is driving me crazy.

Take you pseudo psychology and blow it out your ear.
she probably can see through people's bullshit better and doesn't care that they're hot, if they're assholes.
not saying you're an asshole 'cos i don't know you, but you should be aware that these types of girls tend to be more into a guy's personality than anything else, and looks is just a plus.
fuck.you
I think she knows she should stay away from shallow guys like you because you guys have nothing to offer but your big egos.
Let me give an example. I was out with friends once, and talking to a good-looking male friend of mine when a douchey self-consumed arrogant over-grown frat boy (whose image surfaced when I read your post) approached us and blatantly said "you are much too beautiful to stand here talking to this loser when you could be having drinks with me, I mean look at me." <record screeching> Really?!?! If I weren't a lady, that would have warranted a punch in the mouth.
Not only would you be insulting her, but you are insulting people she apparently cares about. Not smooth, not effective. The answer lies not in what you can get her to see/understand. The answer lies in your perceptions. Take a look inside yourself. If you describe yourself using only one word, would it be a physical trait - you chose "attractive" - or a personality trait. Open up to yourself a bit before you put your foot in your mouth, or even worse, get someone else's foot in your ass. I truly wish you luck, dude.
ASSSSSS HOLE
have you ever thought that she is dating these guys because she reely likes their personalities? if u try to get to know her then she myte like u too and wont be intimidated.
Also you sound fairly superficial and shallow, if you want to get her, grow a personality
Just ask her out dammit. Don't tell her about the ugly duckling thing, and certainly don't tell her that she has confidence issues.
Once your with her (and also maybe when you're trying to get with her) try complementing her. Don't tell her "you have a really nice ass" or "wow you have big boobs" because that will just piss her off and she'll think you're a jerk (although it might help her confidence a bit).
Try telling her that shes cute/pretty/beautiful at first, stuff like sexy or hot will be good a bit later on into the relationship. Also, you should try complementing her on her eyes or other features that arents necessarily sexual (like, nothing about boobs, ass, waist, legs, ect.). Don't make all the complements about her physical appearance either though, tell her that you like talking to her, or that she has nice taste in something. Don't lie to her though, because sometimes you forget about those.
G.L
Most importantly, don't ever tell that she was an "ugly duckilng"
I wouldn't diss on those guys because then you'd be like one of the mean pretty girls that used to pick on her (I know, because I have classic Ugly Duckling Syndrome, or so people tell me). If you come across that way, she sure as hell won't want to date you. Don't mention how you feel about those guys because they could be really wonderful people, and it would make you look conceited ("Gosh, why are you dating those losers when you could have ME?"). I don't think you are conceited, but that's how it would come off to her.
I think with girls like her, being upfront about that is very scary. Maybe if you wrote her a sweet letter and told her how beautiful you think she is, or serenaded her or something like that, that would be less intimidating and more gentle. She sounds like a sweet girl, so do something sweet. She just needs someone to make her feel beautiful so go ahead and do that!
Good luck! Hope it works out! :)