Considering Annie's general tolerance for bullshit, it might. She calls Ken out often enough. Doing so more often will simply be upping the ante. Much as with anything else, she only acts when she sees a reason or purpose to act.

With Ken, it's when she feels he needs to get shaken out of his own head and the cycles of self interest he falls into.

As for the comment on friends, she shrugs, not sure if it is or isn't. "You tell me. Is it?" Watching is all she does - or did - for a long time.

"... I'm glad." This is not the conversation she expected to be having as they approach the restaurant. It's strange. "This isn't an easy place, in it's own right... but I'm glad you can find joy in it."