He didn't want to hurt her, he didn't set out to make her cry specifically, but he knows from experience that sometimes you just gotta let it all go. She needed that, and he pushed a little only because he knew he'd be right here to help her through it. Just like she pushed him to talk about Kate; he didn't want to but he needed to.

Shifting a little closer, James wraps an arm around her, keeping a hand on her back. He wants her to know he's right here, and that she's not alone.