The training wheels probably stems from the fact that his family is filthy rich and he's never had to learn how to bike as he'd have his own limo with his own personal driver to take him wherever he'd possibly want to go, as well as extremely snobby parents who probably thought of biking as something only filthy peasants do, and therefore their little James shouldn't do it either because it's beneath him and would be an embarrassment for the family.
As for him and Jessie, I like them better as only being close friends.
It's such a rare thing to see strong platonic friendships where the two people involved don't end up falling in love.
He was meant to be married to some girl his parents picked out for him, but she was an abusive meanie, so he ran away from home and essentially forfeited his right to inherit his family's fortunes in order for him to live the kind of life he truly wanted.
I'm sure that despite the fact things aren't always going great with their villiany, he's having the time of his life right now.