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The question

My boyfriend proposed in a disappointing manner. It was after he had accepted a (lucrative) job offer in another city, and while I was visiting there. At a farmers' market, an inexpensive ($49) chunky silver ring caught my eye as a souvenir, which my boyfriend suddenly offered to buy – a surprise, as he is tight with money. After paying, he then said: "Would you like to consider this an engagement ring?" Giving a shocked but happy "yes" to the marriage proposal, I said I loved the ring, but it would not work as an engagement ring: It was not resizeable because of a quotation around the band, did not fit my ring finger (only my left thumb!) and did not remotely resemble an engagement ring. Upset followed. I was further embarrassed when his family criticized my wearing the huge ring on the "wrong" finger. Should I have just said no?

The answer

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A man who will later become a good husband can deliver a lousy proposal: I'm living proof.

I have been a good husband, I think. I treat my wife like a queen: bring her coffee in bed, constantly shower her in praise and love. We don't even fight any more. (We used to, especially when the kids were little and we were both tired: I remember once she booted me out of the car on the highway – after pulling over, thankfully. Still, it was about a $40 cab ride home.)

My proposal sucked, though.

Well, I'd been proposing to her almost from the moment we met. She'd smile at me, a little crooked smile I loved, and it'd just come flying out: "Will you marry me?"

Her response was always the same: "I can't take you seriously without a ring, Dave. It's not a real proposal without a ring."

Finally, after four years of cohabitation, I decided it was time to do it properly. (Why'd I wait so long? Go ask it on the mountain. And if you do, the answer will come back from the valley: "Because Dave's an idiot-ot-ot-ot.")

I bought a ring. Made her favourite dinner: steak, potatoes, fine wine. But unfortunately, afterward, we got into a terrible argument. About what, I don't remember.

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The ring was burning a hole in my pocket with the fire of Mordor. Eloquent speech on the tip of my tongue – and my gorgeous girlfriend tongue-lashing me mercilessly. Then, this thought occurred to me: "This ring does have one superpower. It could end this friggin' fight."

So I popped it out in the middle of her tirade. "Will you marry me?" That brought her up short. It took her a moment. She said yes, thank God: but it was through clenched teeth.

(So it worked: but it's a trick you can only use once, obviously.)

Anyway, if I were you, and you love this fellow, and he loves you, I wouldn't let his lousy proposal stand in the way of your happiness. But I detect two, maybe three, other red flags here: 1) cheapness 2) lack of a sense of occasion 3) not very romantic.

The third one's probably the most troubling. I've always said the two most important things you need at the beginning of a relationship are exclusivity and momentum.

You want a man whose love is so strong there is steam coming out of his ears. Ask yourself: If he's lackadaisical and his passion is lacklustre now, what will he be like a decade from now? Two decades? Three?

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Ultimately, the question you have to ask yourself – and only you can know the answer – is whether his proposal was a symptom of a man with insufficient passion for you; or a klutzy slip-up from a loveable lunk who loves you but isn't great with the gestures.

If you genuinely believe it's the latter, why don't you offer him a redo?

Tell him: "I love you, you love me, but I deserve a better proposal. I want a good proposal story to tell our future children. If you want me, I want you to propose properly, with a proper ring."

If he balks, well, then you have a problem. He needs to learn to do things that may not seem important to him to make you happy – and I can think of no more succinct description of the state of (a good) marriage. Might as well start now.

But if he loves you in the way you deserve to be loved – the way you need to be loved in order

to marry someone – he'll straighten up, fly right and propose properly.

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Are you in a sticky situation? Send your dilemmas to damage@globeandmail.com. Please keep your submissions to 150 words and include a daytime contact number so we can follow up with any queries.

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