Thanks JP1692 - that other post adds some balance, and interesting background.
If Gary's ring is worn because of his membership of some elite fraternity, then according to Watchtower's own literature this is nothing to be worried about.
Awake! 8th October, 1951, page 24.
[Rings] Many are works of art, beautiful and costly, and are worn as appropriate accessories to fashionable costumes for the sheer pleasure they give. Others commemorate important events, or are worn as keepsakes in sentimental remembrance of certain individuals or special occasions. Counterparts of ancient signet rings are found in those worn by members of lodges, fraternities, schools, etc. There is nothing particularly wrong with the above-mentioned rings.
Perhaps he has been invited into a "lodge" (Masonic or otherwise), a "fraternity" of "Guardians Of Doctrine", or it was a gift to "commemorate" his invitation to become an HGB (Helper to the GB). I would be very interested in that. If anyone has the time and interest to shed any light on the ring, then I make no apology for being interested in that information.
This post is simply an invitation to share knowledge/research. (So far, I LOVE the comment about it resembling SnapChat!!!)