Jacque and Tyler hit it off on "Coffee Meets Bagel," exchanging messages that quickly became the highlight of their days—especially since Tyler wasn't (and is still not) known for his lengthy or prompt texts. They decided to meet in person at Cafe Delhi in Carnegie. The night before their big dinner, Jacque was walking her dog Suka when a lightning bug landed on her shoulder. Startled, she swiped at it and accidentally cracked her phone screen with her keys, right in the middle of finalizing plans with Tyler. She used speech-to-text to let him know she could still meet up, she thinks, but all she saw was a black panel of glass. Meanwhile, Tyler wondered if it was just a convenient excuse, and the way of the world with online dating. The next day, between meetings at Pitt, Jacque managed to get to a store in Oakland to buy a new phone. She texted Tyler, relieved that her screen was fixed and confirming their dinner plans were still on. That evening at Cafe Delhi, they finally met face-to-face. Their conversation flowed so easily that they lost track of time and were politely asked to leave as the restaurant closed. As months passed, they shared countless moments and deep conversations, leading them to make the big leap of moving in together on March 1, 2020—just two weeks before COVID locked everything down.

The original plan was to propose before the Mexico trip, asking Jacque to go out to dinner the night before the flight. Jacque, consumed with last-minute preparations, declined his invitation to dine out, opting instead for a quiet night in where they ordered take out. Attempt #1, foiled by practicality. And so, Tyler found himself at the mercy of TSA and the unpredictable nature of travel, clutching the ring tightly as they flew to Mexico. Their first stop was Isla Holbox, a serene island renowned for its expansive sandbars that allowed one to wade far out into the ocean. Tyler had envisioned proposing amidst the turquoise waters, under the vast expanse of sky. Yet, the fear of losing the ring to the ocean's depths proved too daunting. Attempt #2, thwarted by caution. Their journey continued to the colonial city of Valladolid to visit Chichén Itzá, a marvel of ancient Mayan architecture and one of the world's wonders. The midday sun blazed overhead, casting sharp shadows over the ruins. Seeking respite from the heat, they found shade under a centuries-old tree near the "Grupo de las Mil Columnas." Seated on a toppled column, amidst the remnants of a once-great civilization, Tyler reached into his bag. He spoke of a gift, leaving Jacque momentarily perplexed—how could he have found time to buy her something amidst their search for her brother's gift for watching the dogs? With a flourish, he produced a bright red box, its color vivid against the backdrop of weathered stone. In that moment, in the sweltering heat and history around them, Tyler asked Jacque to marry him.