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There’s Only One Foolproof Way to Avoid an Engagement-Ring Disaster

It'll still be a surprise, and it'll still be romantic (we promise)

Surprises are wonderful. A gift of exactly the thing your heart desires ranks among some of the best surprise moments you can experience in life, if you don’t count winning the lottery or finding out someone you never liked is now suddenly dead. That’s why getting engaged is so nerve-racking: It’s a double surprise. You want the proposal itself to go well, and you want your partner to actually like the ring you offer.

Easier said than done. What happens when your ring is ugly? You get roasted for it. Ring-shaming is practically a sport, thanks to groups like the one we profiled last year. In turn, shaming women for being shallow, ungrateful, critical harpies is equally common.

It almost feels like a game rigged so no one wins. Figuring out what she really wants might ruin the element of surprise. But a full-on surprise with no previous discussion probably results in a poor gift — one she’s socially pressured to wear forever without complaining, even if she hates it. A ring demonstrates more than just class or carat; it’s a reflection of her personal taste.

What’s more, women have historically had little say in who they’re married off to. Women have long been economically dependent on men for their protection and survival. Women have long looked forward to marriage and engagement and weddings as the end-all be-all of their womanly existence, and many women spend their lives thinking about and planning and dreaming and designing their perfect dress and also their perfect ring. You can take out all the weird backstory now that we’ve moved to something closer than ever to equality. But you can’t take out the preference for a specific type of ring.

Of course, taste is subjective. But the real problem, according to the wide array of ring disaster stories on the web, is poor communication.

Take this story from the Wedding Bee forum:

“I always wanted a larger canary yellow diamond ring on yellow gold. A few months ago my boyfriend asked me to send him photos of the ring styles I liked and I told him exactly what I wanted. His mother called me later and told me that she always wanted a yellow diamond as well but that they don’t have a yellow diamond in the family. Apparently she wanted me to have his grandmother’s ring and he was just gonna take the diamond and change the setting.”

So why is it that it still feels rare for women to help choose their own engagement ring? We concede in every other sense that women are free to choose how they dress, apply makeup or wear their hair. Why continue to insist they wear lifelong jewelry chosen by anyone other than themselves?

Guys, you might be surprised how romantic it is to go through the ring process together without compromising an iota of surprise, romance and chivalry. You might be surprised just how much your relationship will benefit from attacking engagement as a team.

But if your impulse is simply to avoid an engagement-ring disaster, there are lots of ways to prevent it. Here are a few easy guidelines.

Propose With Temporary Jewelry — and Pick the Ring Out Together

Nowadays, couples should’ve discussed the fact of getting married well beforehand to make sure you’re on the same page and both want to marry. That way, you’ll avoid a painful, humiliating rejection in any setting. You just know you both want it to happen, and you’ve agreed to defer to the tradition of you doing the asking.

Yes, the proposal can still be a surprise (see below).

Then, pick (or design) the true engagement ring together. Make it a fun, post-brunch drunken browse that’s no big deal: just asking, just trying on. Or ask what she likes. Figure out her ring size. Talk options. Talk budget. You’re likely splitting all the other bills. Why not this investment?

Never Propose With ‘the Ring’

This point is the game-changer. It’s okay if you have no idea what the person would like. Rings are weirdly specific and may not reflect other aspects of a woman’s general style. And it’s okay if you don’t want to ask them point blank if surprise is a big deal to you, or especially if for some reason that ruins it for you. But the only way around this is not to go buy whatever you think is nice and expect them to jump with joy. Instead, propose with a placeholder ring, either heirloom or a string of yarn or some other joke you two crazy kids would get, like a crackerjack ring, and make it clear immediately that you wanted to surprise them with the proposal, but that you want the ring itself to be exactly what they want.

Even suggest designing one together. When my editor proposed to his wife, a designer, he used a family ring to pop the question. Then, the two sat down to sketch their dream ring and got it made. A team effort. They are both very happy with it, I hear.

Together is the key word here. Making decisions as a team, respecting her taste and agency — all this says good things about your commitment to your upcoming marriage and going through life as equal partners.

Again, make the proposal fun. Use a Ring Pop, or a family ring, or a vintage find. You could pick a simple, sparkly gold band, something she can wear on another finger when the One Ring arrives.

Giving them exactly what you think is lovely or what you think they’d want might sound extremely romantic, but by definition, it means your idea of romance is expecting a woman to love whatever you give her no matter what. While to some extent, gift giving demands that we show appreciate and gratitude for gifts we might very well re-gift or toss in the nearest wood chipper once we’re out of sight, surely no man in love wants the woman of his dreams to have to do this with the ring that symbolizes eternal love.

Let a woman have her own taste. Don’t treat her as a demanding, difficult person for having specificity in the thing she’ll wear every day, which will conjure thoughts of you every time she looks at it. This should be a reflection of the degree to which you see her clearly, for who she is, apart from you, and in now way represent a projection.

This is why gift giving can be fraught. Most women are taught to be grateful and appreciative for everything. The fact that we perform this so often should never be confused with us having our actual needs met. The very idea of dressing a man against his wishes is seen as emasculating. Why should women be forced to wear the jewelry of her love simply because it reflects his taste?

Partially, the expectation that a woman love whatever you give her means that you put a greater premium on gratitude and surprise than making a woman feel actually seen and known. I don’t believe it’s ever intentional when someone gives a bad gift (except of course, when it is), but I do think we owe it to our loved ones to give them not things we want them to want, but things they really want.

Ask a Trusted Friend of Your Beloved or a Person With Good Taste

If you don’t want her to know you’re scoping out jewelry, ask her best friend. Ask someone who knows her taste and style. Be aware that person might very well rat you out to her, because hoes before bros. But it can be an effective and perfectly valid way to ensure you get it right.

When my friend Jack got married to the lovely Wendy, for instance, I recall him asking me my thoughts on some ring ideas he had. I’d met Wendy. She was not my “best friend,” so of course I had never discussed at length her idea of the perfect ring. But from working with her and meeting her, I had a clear sense of her style, which was part Southern belle, part whiskey-drinking painter. I knew refinement and taste were important to her, and that she’d opt far more for bespoke and curated over trendy or modern. I felt strongly that she’d probably want something Art Deco.

But I could’ve been horribly horribly wrong. Which is why Jack was so smart: He took that note, and visited an antique dealer to narrow down some options. But here’s the thing: It was well within the ballpark of her style and taste, and he’d done his homework. She loved what he got her. But he’d asked around and thought very carefully about not what he wanted her to have, but what she’d want.

The ring in such a case might not be perfect, but it will be a clear idea of what your person really loves and wants, and therefore it will increase the odds that it brings them great happiness to receive it.

Give Her Multiple Choices

Hey, most people can barely afford the one ring, much less three. But if you can swing it, you can hedge your best by offering options. Recently, a male model named Dennis Brown gave his girlfriend Atara Dallas SIX RINGS to choose from when he proposed.

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I didn't win #6 rings like @jumpman23 , but I won at life with her, so she deserves #6 Rings to choose from. ??????~ ⏬ What an amazing cast of vendors it took to produce this one of a kind #FairyTail #Proposal Style Shoot. Perfectly elevated by an equally Amazin Gentleman @d.xperience & Woman @ataradallas ~ ⏬ Planned, Designed & Conceptualized @themeit_inc ~ ?: @natevealphotography ~ ?: @stgermainevents ~ Drapery: @justbydesign ~ Attire: @themeit_inc & @rasoolsmenswear ~ ⏬ #Dxperience #BlackLove #proposal #proposals #SettingTheBar #NeverSettle #engaged #engagementrings #engagementphotos #6rings #fairytail #ThemeIt #wedding #weddingring #weddingrings @theshaderoom @balleralert @theellenshow @iamsteveharveytv @oprah @michelleobama

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At one point, the caption read: “I won at life with her, so she deserves 6 rings to choose from.”

That worked out well for him — his Insta bio currently reads “Mr. Six Rings.” But there’s always the risk that she’ll hate all six, in which case, sorry?


You should put all your energy toward avoiding disaster. But if it flops anyway, let’s not make a federal case out of it, and paint your woman as some kind of unsatisfied jerk. Jewelry is extremely personal as is any adornment. Don’t make a woman apologize ever for what she likes or wants to put on her body.

I asked around if any of my female friends had been gifted rings they hated, and one woman told me her story.

“My guy proposed with a ring that looked too much like the one I got in my first marriage,” she told me. Oof.

Yet, his handling of the situation shows that a sense of humor and a little humility go a long way in giving a woman something she’s going to wear forever. It doesn’t have to be a viral scandal. It’s a little thing really, that happens to mean a lot.

“It hurt his feelings a little, but I had told him what I didn’t want,” she said.

But as for the ring itself? “I had him take it back and buy me new tires for my Honda,” she told me. “I settled on a simple gold band once we married. In the end he was fine and the diamonds he’s bought me since have been perfect.”