WHERE IT BEGAN
They met in the summer of 2020—peak pandemic era, when socializing meant choosing your quarantine pod like it was a reality show. Olivia had been living in Jersey City Heights for a while, fully settled into her apartment and her go-to takeout spots. Conor hadn’t moved there yet, but he was thinking about it—and apparently, Olivia’s living room was a good place to start his research.
One warm July evening, he showed up at her door with a bottle of wine, wearing sweatpants and flip-flops like it was a fashion statement. (To be fair, it kind of was.) It wasn’t exactly a grand romantic gesture, but it worked. They sat by the window, music playing low, and talked for hours—about everything and nothing. It was one of those nights that just... clicked.
From there, the summer rolled out like a low-budget indie rom-com. Conor kept coming back to Jersey City—sometimes with better footwear, sometimes not. They wandered the neighborhood, ordered way too much Thai food, and had long, meandering conversations that made the world outside feel a little less weird.
By August, they found themselves at Bradley Beach, watching the waves and trying not to get sand in their snacks. That’s when Conor asked Olivia to be his girlfriend. No fireworks, no dramatic speeches—just a simple question that felt like the easiest “yes” in the world.
Looking back, there wasn’t one big moment that defined it all. Just a bottle of wine, some questionable footwear, and a summer that turned into something real.
07/14/20
OUR ENGAGEMENT STORY
They were in Colombia, visiting Conor’s brother’s wife’s family in Bogotá—a trip that had been in the works for a while. It was the kind of travel that felt layered: family, culture, new places, and shared experiences. One day, they planned a group excursion to Monserrate, a church perched high above the city, reachable only by tram and a steep walk.
The air changed quickly as they climbed. Olivia hadn’t expected the altitude to hit so hard—so different from New Jersey. By the time they reached the top, she was dizzy, lightheaded, and needing to stop often. Conor, unusually insistent, kept urging her forward, a little too focused, a little too pushy. She didn’t know why he was in such a rush.
Finally, they made it to the church. Inside, the cool air offered a bit of relief. Conor disappeared, Olivia assumed he’d gone to get her some water. Olivia sat quietly, trying to catch her breath.
When he returned, he didn’t have water. Instead, he had a question.
No big crowd, no elaborate setup. Just the two of them, in a quiet corner of a church on a mountaintop, above the clouds. A simple question, asked with intention. And suddenly, Olivia didn’t feel dizzy anymore.
They lingered there for a while, letting the moment settle in. It felt like something worth holding close—just theirs, at least for a little while longer.
This was on repeat on Conor and Olivia’s first road trip to Maine.