I'd say the most significant thing to figure out is if she wants to be in on the decision or not. If it's such a complete surprise that you can't talk about it, chances are you haven't discussed marriage enough. Secondarily, even if the ring's a surprise, make sure you're on the same page regarding money. That bill's going to hang around and affect both of you somehow. Also, as FTJ says, there's no law against multiple rings in a long marriage. I remember my parents buying my mom new rings, probably because they must have had enough money on hand to upgrade. A few years later, when my grandmother (dad's mom, who also had multiple rings) passed away, my mom started wearing one of her sets. (Grandma chose to be buried in the ring from her wedding day and wanted her other rings to be used by family members.) I don't know what to suggest if you might be choosing to use a family heirloom. We have a couple of those hanging around. One is the ring my grandmother was saving for her first daughter. There was no daughter, so she then saved it for a granddaughter. With no granddaughter, we all have to agree to save the thing for the next generation?or two or three. I don't know how long that will last. There's been no girl born in my 'immediate extended' family since 1898.