I'd say the reason Chris still wanted Jamie in the end is because of what I'd call the real message of this movie. "Always be yourself, and never be afraid to put yourself out there". Chris said himself that Jamie brought the best out of him and she did.
Without her in the picture anymore he still had all of that anger in him as an adult, and he went on taking it out on everyone around him. Taking better care of his body in the process a long the way wasn't a bad thing at all, but like Samantha James character, he was obsessed with trying to be anything but who he really was..and that's why a relationship between those two was never going to work out even if they tried.
Neither one of them knew who the real Chris or Samantha was but Jamie knew who the real Chris was, as did his mom, and his old friends, Darla and Clark. Chris needed them badly back in his corner, and I'm sure Samantha had some people out there some where too that she needed but sadly we didn't get to learn more about her story since it wasn't about her, and we never got a sequel focused on her which I think would have been amazing around that time period.
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