The Biggest Engagement Ring Mistake to Avoid

This is a cautionary tale — it is the experience of but one man, take it for what it is worth.

My (now) wife and I got engaged in May of 2017, right around the three-year anniversary of our first meeting. As far as engagements go, I like to think that for the most part I pretty much nailed it — under the guise of celebrating said anniversary, I planned a Big Day Out with several fun stops around NYC that culminated in a knee taken on Chinatown’s historic Doyers Street, a “yes” (always a plus), and a surprise engagement party with a host of family and friends.

For anyone contemplating popping the question in the near future, I can wholeheartedly recommend all of the above. What I cannot recommend — and the reason I used the qualifier “for the most part” up there — is making the mistake of designing your partner’s engagement ring without their input. I did it, I regretted it, and while it all turned out perfectly fine in the end, I’d love to help others steer clear of an all-too-common blunder to which I fell victim.

To level-set, I’m not here to tell you that there’s any “correct” way to get engaged. Asking someone to spend the rest of their life with you is a momentous and highly personal occasion, and whichever way you decide to go about it, I salute you and wish you two crazy kids all the best.

That being said, I do believe that we as a culture (and men in particular) have been conditioned over time to think that every element of getting engaged needs to be a surprise. And that the bigger the surprise, somehow the more romantic the gesture. This is folly, and if left unchecked can lead to something like an ill-advised Jumbotron proposal, which — while I did say above that there is no “correct” way to get engaged — most will agree is almost always an “incorrect” way.

This mindset also frequently bleeds into the ring acquisition process, which many have come to believe must be done under cover of night with NSA-level secrecy lest the proposee find out and … what? Become aware that a major life change is on the horizon and have time to mentally prepare for it? Have some agency in choosing a symbol of your union that will be worn, if all goes well, until death? Imagine someone handing you a shirt that you had no hand in choosing — even a shirt chosen for you with a great deal of love and care! — and saying “Here, wear this every day forever.” The whole thing is all very dumb and antiquated and I feel comfortable saying that because, well, I was dumb and antiquated.

Regardless of what kind of ring you wind up getting, it doesn’t take a rocket scientist to tell you that you need to insure that thing, pronto. What you might not know, though, is that while renter’s and homeowner’s insurance do tend to cover jewelry, it often isn’t enough to cover the repairs, let alone the full replacement cost. It also frequently doesn’t cover all-too-common occurrences like, well, straight up losing something valuable.

The folks at Jewelers Mutual Group quite literally have you covered, having spent the last 108 years insuring nothing but jewelry against various unfortunate events. So if that fancy engagement ring you so smartly collaborated with your partner on gets left on a hotel room sink, falls off in the ocean, gets cracked on the edge of a table, don’t worry — they’ve got you. For 1-3% of the cost of your jewelry annually, you get the peace of mind that no matter what lamentable fate befalls your valuables, the experts at Jewelers Mutual will help you replace your piece with a jeweler of your choice faster than you can say “I swear I left it right here…”

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Additionally, outside of the problematic relationship dynamics illustrated by unilaterally deciding on a ring for your partner, there are practical considerations as well. There are things, important things, that you’re just not going to know or be aware of unless you — shocking suggestion — talk about it like a normal human.

In my case, this was a failure to take into account that my wife has very small hands. I knew enough about her tastes to get the metal right and got a stone from her native Australia that I thought was a nice touch, but at the end of the day I chose a style of ring that was just too damn bulky. It was cumbersome, and I could tell from the very first moment I slipped it onto her finger.

And you know what? She would have worn it forever and not made a peep about it. My wife is exceedingly kind and in no way picky. But watching her fidget with it, attempting to find an ideal angle or finger position that just wasn’t ever gonna come, I could tell I screwed up. Eventually we talked about it, and after several rounds of her being super nice and saying we could just try to have it modified to fit her hand and that she would never want me to feel as though my efforts to give her this special thing were in any way unappreciated, I finally was able to convince her with a sentiment along the lines of, “This is stupid. I did this incorrectly. The whole point of building a life together is trying to make each other happy. I want you to have something that makes you happy to put on.” At which point she of course told me that she was perfectly happy putting on this ring, more discussion, yadda yadda yadda, eventually we got there.

Back to the jeweler we went, where in literally 10 (very fun, honestly) minutes we had selected a new ring/setting that would incorporate the same stone and slip perfectly onto her miniscule digit. The original ring got a new stone and became a very cool cocktail ring that she now wears on a different finger and is probably more expensive than any cocktail ring I would have ever purchased normally, but sometimes a valuable life lesson requires a little hit to your wallet. Because when Engagement Ring Version 2.0 arrived and I saw how she beamed when she put it on, I thought to myself, “It’s not about the biggest surprise. It’s all about that face. That was the endgame. I should have been smart enough to know that in the first place.”