In Defense Of Picking Out Your Own Engagement Ring (& How To Do It Right)

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I feel no shame admitting my unbridled love for romantic comedies. I’m loud and proud about Netflix serving me “Indie Romantic Comedies with A Strong Female Lead” as soon as I log in. I might have actually squealed with delight when I realized HBO Go added 27 Dresses into the mix, because that scene in which Katherine Heigl and James Marsden dance on the bar to “Benny and the Jets” is basically everything.

As much as I love a romantic fantasy and whimsical happy ending that sweeps the protagonist off her feet with the perfect diamond ring she didn’t see coming, I will never be that girl.

Because even though I love romantic comedies, I know that life isn’t actually like one. These movies always cut to the credits before the heroine has time to consider that maybe the ring is not at all what she wanted, and now she has to live in quiet resentment every time she looks at her left hand.

See, in the rom-com biopic of my life, that part just couldn’t be left on the cutting-room floor; I am hard to please. To say I am difficult to shop for is an understatement. My particular inability to hide any sort of disappointment when it comes to accepting gifts I do not like is not one of my more likable qualities. Let’s break it down: I’m an only child. I’m extremely particular. I cry if my haircut isn’t exactly right.

I’m kind of a monster-asshole person, but somehow, I convinced someone to love me enough to want to spend the rest of his life with me. However, you can only imagine how this unsavory personality trait made him feel about the prospect of choosing an engagement ring for me.

The first time our engagement came up in conversation in a real way (aside from the time I very seriously requested that there not be a flash mob at Disneyland) was last year, when I brought home the diamond ring I inherited from my grandmother. At the time, Jacob and I were three years into our relationship and had long since admitted that we both knew practically right away that we were meant to be. Marriage had been a regular topic of conversation for some time, but these family jewels made it more real. With sentimentality and cost in mind, there was no question that I wanted Jacob to use the diamonds in my grandmother’s ring for my own engagement ring. However, that meant this was undoubtedly going to be a custom job that required someone’s very critical decision-making — no pressure or anything.

Still, despite being over 30, settled with two cats, neither of us was in any rush to make things legal. But as we passed the four-year mark, nuptial talk increased, along with tension around engagement expectations. At this point, it wasn’t a matter of IF (yes), and not even as much of WHEN (soon), but really HOW (TBD).

Remember what I said about how I react to surprises, kind gestures, and gifts? For obvious reasons, Jacob was feeling apprehensive about proposing.

This all came to a head over Valentine’s Day weekend 2016, when I confronted him about acting prickly about the subjects of engagement and marriage. I felt confused by his recent hot-and-cold attitude about spending our lives together. Wasn’t this already settled?

At my prodding, Jacob finally revealed that he had started thinking (read: stressing) about proposing, and even started saving for a ring, but he was still reticent about the whole thing because of what he perceived to be my very high expectations. “Heather, you can’t have both the proposal and the ring be a grand surprise,” he told me. “It’s too much for…you.”

At first, I was a little perplexed. Not once had I ever thought the ring had to be a surprise. I’m self-aware enough to know what kind of Green Beret landmine operation that would be, no matter how many emails I sent to my best friend with rings I liked, with paragraph descriptions of why I liked them. And I truly had no expectation of how I’d like a proposal to go down, either; I was going to cry hysterical tears of joy no matter how he did it because it was my goddamn marriage proposal!

I felt terrible about Jacob’s confession. I didn’t want him to feel anxious about any part of this, and I certainly didn’t want a stupid ring to put a strain on our relationship.

“The ring doesn’t need to be a surprise!” I said, relieved that this weirdness between us could be fixed. “I know we’re getting married. I know I’m stuck with you forever and ever. This is just a fun thing we get to do beforehand, so let’s go look at rings. Besides, knowing myself, I’m going to pick out something I never thought I’d like.”

Two days later, we drove to the Jewelry District in Downtown L.A. without a plan other than Yelp. This is how we found Oscar. He was open, accepted walk-ins, and had a solid five-star review. As soon as we walked into the small storefront in a large office building, a saleswoman asked, “Engagement ring?” like she was guessing my coffee order. It was a good reminder that even though this was kind of a big deal in our relationship, the jewelers dealt with this type of sale multiple times a day.

Staring into the glass cases, I was immediately struck with the impossible, yet stereotypical, wish for something timeless, and yet completely unique. After trying on and rejecting the ring I thought I’d always want (solitaire with diamond infinity band), I was left Goldilocks-ing three rings of varying degrees of complexity and bling.

Oscar, the jeweler, came over to see how I was doing. I showed him my choices, and told him about wanting to use the solitaire from my grandmother’s engagement ring. He looked at the ring with more diamonds than I would ever have chosen (and only reluctantly tried on after the saleswoman suggested it) and assessed that this setting would work well with a vintage stone, which wasn’t the case with all of them.

I looked at Jacob. We both agreed that even if we had all the money in the world, we wanted to use my grandmother's diamond. And, even though this ring wasn’t like anything I would have ever picked out myself (as I predicted), I kind of couldn’t stop staring at it. Just like that, it was decided. I sat down with the jeweler while he took detailed notes on my insanely precise instructions and desires. He quoted us a very reasonable price, and all Jacob had to do was put down a deposit and bring in the diamond when he was ready.

As we drove away, Jacob asked if I thought we should get a second opinion since it was our first time looking.

“Absolutely not,” I said.

“How come?”

“Because there are so many beautiful things in the world. We could go looking at rings every weekend for the next month, and I’d fall in love with a new ring every time. Then, ultimately, I’d say, ‘Jacob, I love all three of these rings equally. Surprise me with one.’ Then, I wouldn’t really know which one I wanted until I didn’t get it. So, let’s just keep one great option on the table.”

Three months later, Jacob surprised the hell out of me with the perfect proposal and the perfect ring — it was so much more beautiful and special than I could have imagined. He asked me if I wanted to marry him in our living room, while our cats ignored us, and then surprised me again with a day filled with my best friends and family. Even after four-and-a-half years together, many conversations about marriage, and one trip to pick out my ring, the proposal still shocked me into very uncharacteristic tears and blubbering.

It wasn’t a rom-com proposal, and I’m glad. When people compliment my ring and say that Jacob did a great job, I always correct them. WE did a great job.

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