sorry about that I've been away for a few days. it was in the first season, when Tony told Dr. Melfi that he loved her. It was actually the episod after that.
He made a reference about her disregarding his emotions, and she said "How does that sit with you?"
Later on in the same meeting, he mentions his girlfriend for the first time. She said she was surprised that it took so long to say something about his girlfriend and he said "How does that sit wiht you?"