I have a theory. So Emma said herself that she had a crush on him, but Tom being very young probably didn't know what to do and defused it by saying he saw her as a sister. Then, she was heartbroken and did not go for him after blooming into this pretty lady. She did well in school and became really quite formidable and he was probaby thinking she's too good for him and didn't make the move because he messed up earlier. You can see they were always bashful around each other and Tom really seems to respect her.
Now Jade came along and when she heard of his interest, she made herself available to him like Emma didn't (to shield her hurt heart). Long story short, Tom is now is Jade and Emma is heartbroken like always. You will see she even picks boyfriends that looks like him. I think they were two people who were meant to be but just missed each other. Hope they can be together some day.
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She probably wouldn't let him do to her the same things the groupies let him do to them1