Ему было трудно понять, чего, собственно, она от него хотела

Не was having a hard time understanding / It was difficult / hard for him to understand / He was having difficulty understanding / grasping / what exactly she wanted / was after from him.

He was hard / difficult to understand означает «Его было трудно понять», например, потому, что у него сильный английский акцент.

Тебе обидно?

Are you hurt? / offended? / upset?