Harold is a normal man from Iowa who has somehow ended up surrounding himself with incredibly traumatized, dangerous people, so he is fairly accustomed to this kind of look. It reminds him of Root just a little, in way that makes him miss her sorely, but also makes him rueful. She'd initiated their relationship by kidnapping him, after all. This is already going substantially better.

"I wouldn't presume to speak for her," Harold demurs, because he loathes sharing personal information of his own or of anyone he cares about, and that includes informed speculation-- "But considering she rejected my offer several times before finally acquiescing, I think it's safe to say redemption was not her chief motive."