W can't operate in an R in the way you describe unless you facilitate it. I again urge you to take some ownership here and set some boundaries as to what is acceptable behavior from anyone in any kind of R with you.
W may in fact not know her own feelings or desires and may thus be unable to communicate them. My sense is that she loses her identity easily in her efforts to be what people want and to make them happy.
She may thus have initially found a kind of faux freedom and acceptance in a new R, because she didn't yet know who she had to be to make him happy. As she sacrifices more of herself (becomes more enmeshed with him), those attractive features of that R will diminish. But, as long as she remains enmeshed with you, she won't find that missing thing -- *herself* -- in an R with you. All you can do here is set boundaries and quit managing her feelings, quit being reactive to her. That is, all you can do is extract yourself from the enmeshment, it takes two to play. But, you keep playing.
Example: this obsessing over how to micromanage her feelings because you have contracted for employment for a date in the future on which it might turn out she wants your company. If she is unwilling to work on a solution to this, it is her problem. Tell her so.
Back to the ring... If you put on a tie one day because it reminded you of a great day with your W and then she criticized the tie and gave you angry looks for wearing the tie, just how able do you think you would be right now to tenderly share with her that it was really a loving thing on your part?
She doesn't trust you or her feelings for you. If I am correct that the ring was a positive sign from her, then she took an emotional risk and made herself a bit vulnerable to you. If so, it did NOT pay off for her and she certainly would not be up for taking even greater risks by telling you directly the meaning of the ring to her. I mean, she already pretty much did when she told you it was because of the other ring that YOU GOT HER.
OM is NOT the problem. The problem is your Ws unwillingness to committ to an exclusive M with you and to work on it. She is unwilling to do so for her own reasons. Those reasons are still there or OM wouldn't still be there. Your W will have a very hard time cutting ties with OM because of what it will mean to her about herself when she does so. Stringing him along as a friend or BF will allow her to avoid her guilt and pain about him and make her feel less stupid, cheap, and shallow. As long as you tolerate this, stringing him along is the path of least psychic resistance.
But, I agree with you that there does come a time when YOU need to change what you are doing, which may include no longer tolerating OM. This is YOUR CHOICE. If you make the choice not to tolerate OM when it is less painful for her to go with him, she will go. That is a risk you either choose to take or not to take. If you tolerate OM beyond a certain point, it will destroy your R. That is a risk you either choose to take or not to take.
There is nothing attractive about a P who doesn't require decency and respect in an R.