It was June 14, 2020, the first weekend post-Covid restrictions in Chicago, when fate smiled upon Jason and Diana at a brunch that would reshape their lives. Their mutual friend, Chandni, reserved two tables, and a twist of fate led to Diana unexpectedly joining the brunch. With a playful prediction, Chandni teased Diana, "Jason will for sure hit on you." True to the jest, Jason arrived fashionably late, securing the last available seat at Diana's table. Initially finding him a bit bold, Diana's perspective shifted as she embraced Jason's humor, discovering an unexpected charm. Their connection flourished over shared passions—travel, live music, and their love of good eats. Only three months after that fateful brunch, Jason and Diana embarked on their first adventure together, a road trip through the scenic landscapes of Oregon. It was during this journey, at Hawkins Winery with a breathtaking view of Mount Hood, that Jason asked Diana to be his girlfriend. Their wanderlust led them to explore other corners of the world, creating memories in Hawaii, Banff, and Portugal. Each destination deepened their connection and solidified the bond they discovered at that brunch. In tandem with their travels, music became a powerful thread weaving through the fabric of their relationship. Diana soon embraced Jason's passion for Above & Beyond, turning what was once one person's obsession into a shared love. Their journey together through music took them to Above & Beyond shows in multiple cities – LA, Austin, Montreal, London – and especially at home in Chicago, where they found a rhythm that mirrored their growing closeness. From brunch banter to road trip romance, from mountaintop proposals to global escapades, Jason and Diana's love story continues to grow through a lively playlist of shared adventures.

In the heart of Chicago, Jason orchestrated a surprise that added a new chapter to their story. What Diana anticipated as a simple lunch and the usual concert transformed into a cherished memory. For a touch of nostalgia, Jason chose the same restaurant where they had their first dinner for a lunch date. Diana, intrigued by this uncharacteristic planning, was pleasantly surprised. Her suspicions grew when Jason ordered hot tea instead of his customary cocktail. Mischievous curiosity led her to check his coat pockets, but the secret remained safe. As they strolled along the Chicago Riverwalk, the iconic Constellation statue provided a picturesque backdrop for Jason's proposal. With a ring crafted with love and the cityscape as their witness, Jason and Diana's love story took a magical turn, forever marked by a surprise proposal by the river.