By Spring 2023, Elizabeth and Josh found themselves designing her engagement ring. This was a happy time, as their vision for the ring came into focus.

But despite Josh’s best-laid plans, proposing itself turned out to be much more of a trial:

Chapter 1:

The journey begins (or doesn’t)

Despite the emphatic guarantee from their ring-maker that the ring would not be ready until August, Elizabeth was convinced an elaborate plot had formed to propose to her at the end of an epic hike.

The hike took place in Vancouver, British Columbia, where Elizabeth, Josh, his sister Caitlin, and her roommate Em were going to scale a mountain with three glacial lakes. The third and last lake was at the top of the mountain. As she approached each lake, her anticipation grew, and with every missing proposal, her disappointment. When finally they came to the last lake, and Caitlin and Em had left them on their own, Elizabeth was sure the moment had arrived.

Josh was sure the moment had arrived as well.

By the icy-blue near-freezing lake, surrounded by snow-capped mountains, Josh pulled Elizabeth aside and, reaching towards his pockets, he asked her to hold something for him. He then whipped off his clothes, passed her his pants, and used the beautiful icy lake as his own personal cold plunge experience.

Disappointing for Elizabeth. Josh notes that he had great fun.

Chapter 2:

The journey begins (and promptly ends)

The next attempt at a proposal was, unlike the first, an attempt at a proposal.

The couple spent the day at the beautiful Longwood Gardens, an hour or so away from Philadelphia. The sun was shining, the grounds were gorgeous.

Things were planned perfectly. Too perfectly.

In fact, the only thing that could prevent the happy occasion was the freak lightning storm that hit - and persisted - right as their botanical garden wanderings hit their climax, derailing the tightly wound timeline entirely. And then the backup location, an old famous book cottage, closed before they could reach it.

Chapter 3:

The journey begins (and keeps going, and going):

But in true Josh fashion, he didn’t give up. He booked a trip to Montreal, where he had lived as a child, and allowed for several days of proposal opportunities.

But the main plan, carefully developed with the help of Instagram, Reddit, Weather.com, and Google Maps street view, was to bring Elizabeth up Mount Royal on their first full day and propose at sunset over the city.

This second time around started out ominously. Less than 24 hours before the planned proposal, Josh’s photographer suddenly canceled.

Undeterred, Josh came up with a cunning plan. He would start their visit off by bringing Elizabeth to Montréal's Underground City—a perfectly reasonable and popular tourist destination.

Then, under the guise of exploring the Underground City, he would simply drag Elizabeth to 4 different tech stores, entirely ignoring the rest of the space, where he'd proceed to casually explore only their iPhone tripod options—and then spend far too much money buying two (to be safe!) of them.

This didn't arouse Elizabeth's suspicions in the least.

The day of the proposal, Josh packed everything carefully into his little travel backpack, and they started off the perfect proposal day with an Uber to the stunning Notre-Dame Basilica. From there they walked the elegant streets of Old Montreal to a nice little brewery on its edge.

It was there, smiling, loving, drinking, sitting in the warm sun, that Josh asked Elizabeth "Can you pass me my bag?" and she said, "What bag?".

Fun ensued.

Once they had tracked down the Uber driver, in whose car they had left the bag, and waited an hour for the drop-off, they continued on, undefeated, to a cool speakeasy downtown.

They were slightly behind schedule, but not one to ruin the experience of exceptional cocktails, Josh waited until moods were exactly right to move on to Mount Royal and the proposal.

"Exactly right" happened to be about 10 minutes before sunset... about 25 minutes away from the proposal spot.

And so Josh quickly packed up a happy, slightly-tipsy Elizabeth and told her that they now must take a shortcut up several flights of mountainside stairs to get to the lookout on Mount Royal because... "it's nice, you'll love it."

She didn't love it.

In fact, they reached the top panting, sweating, only to find the sunset blocked by clouds and the plateau swarming with tourists taking photos.

Josh, in his wisdom, suspected this wasn't the moment. And he resigned to try again another day.

Chapter 4:

The journey concludes (finally)

Having concluded that the central error in all previous plans was, well, having plans, Josh pivoted.

He looked at several cool neighborhoods to explore, chose several potential proposal spots, and carried the ring in his pocket everywhere they went. He would wait for his moment, no planning necessary.

A few hours later the sign came. Walking in a park he heard Elizabeth say, "A duck!" in a voice that she reserves mainly for sightings of small animals and other moments of profound happiness.

This was it. But how to distract her? (The duck had, sadly, moved on.)

He lucked out. A puppy, clearly sensing the import of the moment, seized Elizabeth's attention. Josh set up a camera, grabbed the ring, and once Elizabeth was back in front of him, he asked her the question they’d both known the answer to long before.