I get the story is supposed to make the reader sympathise with him, but it does a poor attempt in doing so. James still was a general jerk, he had to kneel down to his buddy’s commands and wishes to a ridiculous degree, and the story doesn’t explain why he teased her upon first realising her identity in chapter one with the nickname. Either make him a complete douche from high school to the beginning of the story, or make him a misunderstood bad boy with a good heart and intentions - but the story decided to do both 
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