Here's the scenario...He's 17, she's 21 and kinda rich. She's probably just using him as a boy toy. He can go in and get some experience, and look at it as that. Because any time there something about "you do this", she will remind him of his place in all of this.
Just enjoy the ride, but do not do the wearing the heart on his sleeve.
Young ladies today, are not very much ladies, they have more game than a lot of dudes, in fact many act like the dudes in the relationship.
Let young Hustleman earn his Jedi stripes, but if the battle gets thick pull him aside, just a tad. But the battle of the heart is something we all have to learn on our own...and it's better sooner than later.