Tyler first heard about Natalie from their mutual friend, Maddy, who was convinced they would hit it off. They finally met during Tyler's visit to Kansas City, MO, where a fun weekend of pool parties, a Chiefs preseason game, and a night out in the city brought them together. Bonding over their shared humor, sports knowledge, and love for pizza, their connection grew even after Tyler returned to New York City.

Tyler convinced Natalie to spend a weekend in NYC visiting him. She was encouraged by her friends to go which set the stage for an unforgettable first date. Tyler surprised Natalie with an open-door helicopter ride over Manhattan which came with an unexpected private flight back to the city. Over the course of the weekend Natalie met Tyler's friends, they shared lobster rolls at The Frying Pan, had dinner at Pier A - overlooking the Statue of Liberty, and watched the Chief's game in Central Park.

COVID hit six months into Natalie and Tyler’s relationship. When the pandemic started, Natalie, like many others, started working virtually. She and her dog, Frankie, made road trips from Kansas City to Colorado to visit Tyler. Initially planning to stay for a week or two at a time, these visits soon stretched into full months. During this time, the three of them grew closer in Colorado. They enjoyed their time hiking, having picnics at Commons Park, and the many Jeep rides in the mountains.

Tyler had been on the hunt for a new job and had been interviewing for various positions. One weekend, he traveled to Kansas City for the wedding of one of Natalie's best friends, Lauribeth. Before reaching the highway from the airport, Tyler couldn't wait to share the news and surprised Natalie by telling her that he had got the role within Anheuser-Busch in Kansas City. They spent the entire weekend celebrating with friends and family, making the news even more special.

Tyler and Natalie enjoyed a long weekend getaway in one of Natalie’s favorite destinations, Sedona, Arizona. They crossed off a bucket list item with a hot air balloon ride over Sedona’s Red Rock Country. The weekend was filled with sightseeing, visiting as many foodie spots as possible, and hiking around Sedona. After exploring some of Sedona’s popular trails one day, they ended the at Lover’s Knoll to watch the sunset with a bottle of wine. As a random hiker agreed to take their photo, Tyler knelt down and proposed. They spent the rest of the weekend celebrating!