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A Decent Proposal
Recently engaged, Tiffy Thompson surveys the proposal landscape to see how the kids are popping the question these days

I recently accepted a marriage proposal. That someone actually asked me to marry them is nothing short of miraculous, and I’m sure my mother had resigned herself to a life of quiet desperation. He initially attempted on September 11th, then on Friday the 13th, but was cock-blocked by tragic history and filmic horror. When he attempted the following Saturday, he was soundly cock-blocked by my best friend who corralled me into a rare road trip. Fed up with trying to execute the ‘perfect’ engagement, he proposed the next week after I finished an unflattering morning workout. I thought he was adorable.

In matrimony, as in crime, the devil is in the details. Your partner will remember, with precision, how you propose. Toronto-based planner Lida Elias has spun this inevitability into a clever business arrangement. She plans dates — and proposals — which can make the most hapless and time-sapped partners appear attentive and detail-oriented. She will orchestrate an experience that will make you look like “the most imaginative, thoughtful and caring person in the entire world,” an arguably tall order. Her business idea was borne out of several uninspired dates when she was single.

“A lot of guys just don’t put any effort or thought into dating. They just show up. So if this is all you got, then it’s not really going to get much better,” she said. “It doesn’t have to be anything extravagant, it’s about just putting time and effort into getting to know the person, listening to them, finding out what they like and don’t like, and then taking those cues.”

Through savemydate.ca, she has planned fully-customized dates to salvage anniversaries and arrange proposals using military-style reconnaissance. She has chartered helicopter tours of the city and arranged private dinners with personal chefs followed by champagne toasts (complete with a photographer that just happens to be lurking nearby). So far, she boasts a 100 percent success rate (no rejections). But is having a pro arrange your proposal excessive, or worse, tacky?

“I’m sure people could come up with some pretty bad-ass proposals if they were to fork out some dough,” noted Chad Hammond. “I could see paying a waiter a little extra to put a ring on the dessert or hire an opera singer to show up and romanticize the pre-question moment.” He proposed to his wife of seven years after 102 days of dating. The number 100 was significant because Korean couples celebrate their anniversaries every 100 days. “I knew that I was going to marry her and the 100 day anniversary felt like a good opportunity for the proposal, but it fell on a Wednesday. I decided to wait two extra days until the Friday when we’d be going out to do it. However, when we did make it to the bar, she became somewhat estranged and moved to another table to do bar shots with a bunch of dudes. This really wasn’t like her, so after we left the bar, standing in the middle of the street, I said something like; ‘what the hell is wrong with you tonight? Did you want me to ask you to marry you or something?’ Then I caught a bashful look in her eye that led me to believe I was safe to ask, so I got down on one knee in the middle of the street and asked.”

Sarah Boesveld’s fiancé asked her on the steps of her own personal country music heaven at the Ryman in Nashville. “We sat down and he fished the ring out of his pocket and popped the question. In a lot of ways it was a very thoughtful and pretty traditional. I thought it was lovely… simple and heartfelt. And then we went to a honky tonk to eat deep fried pickles and down tequila shots.” She’s a little baffled by the idea of paying other people to plan proposals. “I suppose some would be flattered, but in my mind, dude’s already carefully chosen and bought a ring for you – are you really that high maintenance?”

While everyone remembers the details, some would prefer not to know that these thoughtful touches were the product of an external planner. They want to think their partners are operating out of starry-eyed infatuation rather than IOC-level planning. “Some women don’t like it,” said Elias. “So some guys will keep it secret. Because they want to take the credit for it. I don’t care either way, as long as they’re happy and the date is memorable.” Still, others are happy to know that their partner cared enough to attend to these flourishes.

Jeff Raney tackled his proposal with aplomb, without outsourcing. “I had two engagement rings, both inherited from grandmothers. We had spent the previous week on vacation with her four- and six-year-old nieces and they love the game which hand? So I put one ring in each hand.  She was sitting down I knelt down in front of her and said, ‘Which hand?’ She rolled her eyes and said, ‘Really?’ I said, ‘Yeah, pick a hand.’ She tapped my right hand, I opened it up, she saw the ring and asked me if this was what she thought it was. I said, ‘Sure, why not? Will you marry me?’ She said, ‘Yes.’ Much happiness ensued. I think proposals are necessary. It should not be a big production. I would not pay someone to organize it.”

Some, not wanting to wait around for proposals either of personal volition or an act of commerce, just complete their own orchestrations. “I had like twenty bucks in the bank,” said Lynne Rasmussen-McDougall. “So I made him this giant ring out of tinfoil with a bouncy ball ‘stone’ and proposed. I believe he was actually planning to as well, but he had very elaborate plans involving a treasure map and a canoe. I kind of figured it would never happen. So I took the bull by the horns because I might have been waiting for years if I hadn’t.”

Others are not so eager to have a big scene. “He asked regularly, but mostly in a casual way or in some sort of amused reaction to something I did or said,” wrote Alya Fortunada. “One day, he even asked in Walmart. None of this was pathetic, just always casual, and not often. It happened maybe once every year.” She eventually accepted. “Had he done something grand and public, I think I would have been mortified.”

Elias’ favourite part is the reactions she gets. “I love seeing the pride and delight on the girl’s face when she sees what her fiancé has gone through to make the day special for her — seeing the ‘yes’ and the tears, and seeing people happy. That’s my favourite part. I love love.”


Find savemydate on Twitter at @savemydate or visit their website.


Tiffy Thompson is a regular contributor to Toronto Standard & The Grid. Follow her on Twitter at @tiffyjthompson. 

For more, follow us on Twitter at @TorontoStandard and subscribe to our newsletter.

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