This is the 7th time (or pretty close to that number) you've brought up the question if you should talk to your W. It seems to me that you are anxious about the possibility of having W viewing you in a negative light after being served and wanting to "talk" sense into her on the D path. Trying to reason with her and hoping she'll see the "light" on her choices.
Am I pretty close in reading you here?
Advice?
Sit on that discomfort sofa in our St. Elmo's Fire bar and work through your feelings on this. Bets aka Underdog and I have plenty of sofas to choose from. Just to let you know...the yellow one is Bets...so might want to avoid upsetting her.
You need to really leave no stone unturned while sitting on the discomfort sofa and examine why you feel this periodical (or constant) urge to talk with W. Dig deep. The answers are all within you.