Despite living just a few miles from each other and frequenting many of the same hang-out spots, Chris and Tiffany had never crossed paths. One sunny July afternoon, a bored Tiffany found herself browsing the dating site Plenty of Fish and stumbled across Chris's profile. Immediately, Tiffany noticed his kind eyes and genuine smile and took a moment to send Chris a message telling him exactly that. It wasn't long before Chris responded in kind and the two hit it off quickly. On August 26, 2017, Tiffany and Chris went on their first date. Both were relieved to find that neither had been catfished. They were even more pleased to discover the chemistry online was even better in person. On December 23rd, Chris drove Tiffany to dinner with a custom playlist of all the R&B songs that reminded him of her playing over the radio. That evening, over 5-star steaks and wine, the two finally made things "official."

On May 11, 2019, Tiffany and Chris touched down in Mexico for their first international vacation together. The hotel, Breathless Riviera Maya Resort, was gorgeous and both were excited to explore the grounds and enjoy time on the beach. What Tiffany did not know was that Chris had been quietly planning a proposal for months. He secretly shopped for rings with Tiffany's best friend (and now maid-of-honor) then lived in fear for weeks as the ring lay hidden in their apartment. He called the hotel days before the trip and worked through the language barrier to arrange for a photographer to be present during the event. On the first night of the trip, a nervous Chris joined Tiffany for a romantic dinner for two on the beach. The mood was perfect and Chris was poised to pop the question...except the hotel staff were entirely unaware of the plan and Chris was forced to think on the fly! Nonetheless, Tiffany was completely surprised to open her eyes and see a teary-eyed Chris with one knee in the sand and a ring in his hands. Still in disbelief and overwhelmed with love, Tiffany said YES!