Hmm...i don't really think of an anime in particular, but i think the song has some potential and i'd like to see what could be done, with it.

So, since it deals with apparences and realities, i would propose a match with:
- the character of faye valentine, from cowboy bebop, (of course "cowboy bebop", as if there weren't enough of them already...

"-julia: ...miss valentine.
-Valentine: why...why do you know?!"]).
- a female character from the grandia saga ( mainly because of the chorus "i can be a crook or your lover" [hey! that would be a cool match for valentine's lover in cowboy bebop ep' "my funny valentine"]...yep...no can do

- nabiki, from ranma (the line "you think i want those things 'cash, car, diamond rings'"...could make a video such as phade's "material girl"...^^; not really convincing, but i spare some ideas)
- vash from trigun because of the line "you're scared of the homeless guy; think he's gonna wanna start a fight.
Never judge a book by its cover", but mainly, every anime that would go with such a song as Phil Collins "another day in paradise".
One sure thing is: you're gonna have to cut the song--christina milian likes way too much her chorus...^^;;
Here are the lyrics:
When You Look At Me
Christina Milian
Do do do do do do do
Uh huh
Tell me who do you think you see
You're standing in your corner looking out on me
You think I'm so predictable
Tell me who do you think I am
Looks can be deceiving
Better guess again
Tell me what you see
When you look at me
You're probably thinking that I want those things
Cash, cars, diamond rings
Thinking on my side the grass is green
But you don't know where I've been
I could be a wolf in disguise
I could be an angel in your eyes
Never judge a book by its cover
I could be your crook or your lover
I could be the one or the other
If you'd look beneath you'd discover
You just don't know me
Tell me who do you think you see
You're standing in your corner looking out on me
You think I'm so predictable
Tell me who do you think I am
Looks can be deceiving
Better guess again
Tell me what you see
When you look at me
Do do do do do do do
Uh huh
You look at your neighbour thinking "what a guy"
'Cos he's got a nine to five
And I bet you don't realise
He stalks you while you sleep at night
But you're scared of the homeless guy
Think he's gonna wanna start a fight
Never judge a book by its cover
I could be your crook or your lover
I could be the one or the other
If you'd look beneath you'd discover
You just don't know me
Tell me who do you think you see
You're standing in your corner looking out on me
You think I'm so predictable
Tell me who do you think I am
Looks can be deceiving
Better guess again
Tell me what you see
When you look at me
Do do do do do do do
Uh huh
Tell me who do you think I am
Huh
You don't even know me
Well did you think about this
I could be your crook or your lover
I could be the one or the other
If you'd look beneath you'd discover
You just don't know me
Tell me who do you think you see
You're standing in your corner looking out on me
You think I'm so predictable
Tell me who do you think I am
Looks can be deceiving
Better guess again
Tell me what you see
When you look at me
Tell me who do you think you see
You're standing in your corner looking out on me
You think I'm so predictable
Tell me who do you think I am
Looks can be deceiving
Better guess again
Tell me what you see
When you look at me