A: If she really loves you, it won't matter whatever ring you give her even if it is quarter machine ring. All that matters is your committing yourself to her. If she doesn't appreciate that then she doesn't deserve you.
A: I honestly think he really likes you but he is afraid of getting rejected or played by you again. I feel you should let him know how you feel about the relationship and where you want to go with it. Speak up about what he has said to you and ask him if he is serious.