First, the the story of Robin is as tragic as Batman, even worse with the loss of his entire family. He is a circus traveler so he has no home. Essentially when his parents are murdered at the carnival, he is basically homeless and orphaned.
This is the idea of a Robin that could work in the Dark Knight's World:
Now you have a depressed, vengeful, acrobatic, trained kick-boxer, lonely teen who is a person that is hustling for money, including bike races, etc. Now this kid is equipped with nothing more than his clothes and armored bike jacket, that "conveniently" is semi-dark red and black. He is encountered by Batman during his vengeful endeavor and sees Batman’s route is the way to go. Now during the whole time Batman knows who this mystery vigilante is, but doesn't see him as a threat but rather a bad adolescent kid that doesn't listen. Robin tries to tag along with Batman, but Batman is able to separate in his ‘ninja’ mode from Robin. Over time, Robin catches on. He learns quickly from Batman, and keeps up from time to time. (Batman’s abilities are not diminished. He is still able to ‘shake’ him the majority of the time.)
Robin never discovers that Batman is Bruce Wayne. Bruce Wayne never decides to take Robin under his wing. Rather, he feels that this kid is too much of a risk for his dual identity. In the course of Batman's battles, he encounters a situation that he isn't prepared,. He gets trapped and knows that this is it-- he is going to bite the big one. Robin being the one always chasing down Batman, finds him and rescues him. Batman still being himself doesn't thank him but notices that Robin is now valuable but not to the point of being a partner but rather an ally that he can ask for assistance at times.
So really the only way Robin can work is that Robin is his own person, and he really isn't Batman's partner but rather this vigilante who seems to get himself into trouble with the criminals, and can handle his own, at times. Batman really encounters him because he is either rescuing him from being killed, needs his help at certain moments, or Robin is following him. Now the conclusion of the story should be that Robin ends up working for Bruce Wayne because he notices this is the right way that he should receive money. Dick Grayson eventually discovers a hidden "bat-cave" within Bruce Wayne's building. Thus he discovers Batman's true identity. Dick sees this as an opportunity to continue his vengeance on his family’s killer. He proceeds to steal a spare Bat-suit. Then he renames himself Nightwing. This could lead to an off shoot film that would be cool in itself.
Now I suck at drawing but I would love to describe the Robin that could work as a Nolan-esque Robin. Picture this guy who is a 6'0 athlete, with biker armor jacket that's semi-dark red and black, with gloves, black armored leather pants, with black steel toe boots. He uses a one strap back pack to carry his gear (the strap is conveniently dark yellow) and at times carries a staff to fight with or really picks up anything that is available to knock his opponents out. He has a black t-shirt that he uses for his mask, kind of a Zorro look. This idea of a "contemporary” Robin could work in the Chris Nolan movie, as a one-time deal instead of being a boring partner for the next few Batman movies.
What are your thoughts? (Hope Chris Nolan reads this)