How do you ask for an upgrade for those that were sucessful?

Here's what I did. For our 20th Anniversary, my DH gave me a large budget for my present. He hates to shop and knows I'm picky. So I designed a 3-stone ring that uses my original 1-carat round stone and paired it with a 3-carat center and a second 1-carat stone. It turned out spectacularly. I am at my 25th anniversary this year and I am in love with the ring every bit as much as when I picked it up. I love that I used my original stone too.

But I did not ask my DH for the upgrade. He asked me what I wanted for our anniversary.

I have always said that my DH is the diamond that counts. We still like each other after 25 years.
 
It really interesting with everyone's perspective. Some have sentimental value and some it's just a ring. The larger ring would be so nice. But setting aside money and approaching it seems like a great idea. I don't need him to buy it as I can buy it myself. But would be nice as a gift from him. ;)

If it really bothers your husband (which is seems to), why not approach it as asking for a nice right hand ring? If you get a nice ring out of it, does it really matter if it's an engagement ring upgrade or not?

I don't see it as an engagement ring upgrade if you have to buy it for yourself & your husband is opposed to the idea. To me it's like a single girl going out and buying her own engagement ring & just telling her boyfriend that they're engaged.