You mean like during the entirety of his Godfather playthrough, where Leanna browbeat him for hours while he played a game she'd already beaten?
ETA: this is probably my favorite TIHYDP. It's almost no time at all before they're sniping at one another and there are some moments when she really cucks him. He starts doing this thing where he talks much louder than her to drown her out because he's too much of a pussy to tell her to shut up or cut the stream. It's one of the strongest examples we have of what their relationship was really like and how Phil deals with face-to-face conflict, along with how much of a shrinking violet he is when it comes to women.