My plan has always been to pass my wedding set onto my grandchildren somewhere far down the line, since I want to keep my diamonds within the family, and I am by nature a sentimental person.
As far as giving cash to one of my children in order to help them afford a wedding ring, I am on the fence. If my child had a history of financial irresponsibility or random acts of financial spontaneity, or was in a relationship that seemed unhealthy or instable, then no, I would not just hand over cash to secure an engagement ring. But if my child had shown me solid financial understanding and personal responsibility, and had a solid relationship that I thought was healthy and long-lasting, then I might consider gifting a sum of money to help make a happy couple's dream engagement ring come true.