Was he honestly asking that? Nick was just thinking that maybe he was finding some even footing, and then Henry had to go and rip the rug out from under him again. His equilibrium was shot, and he needed to find a way to rectify all of this.
"Of- of course," he said, stumbling over his words as he regained control of his tongue. "We already are! You stood up to Lucifer, Henry. And you are getting your life together. Of course we are proud of you. We love you too." He stood up and leaned over Henry to pull him into a much closer hug, rubbing his back gently.