Keena moved to Chicago in July of 2019 to begin her anesthesia residency. Shortly thereafter, she downloaded the dating app Hinge to see if there were any eligible bachelors around town. Luckily, Ben had been on a few datings apps throughout the years when their virtual paths finally crossed. They exchanged their first message on July 9th, had their first date at Forno Rosso pizzeria on July 13th, and that was that.

Ben took Keena back to her alma mater in the Bay Area to celebrate her 31st birthday. Having never been to Northern California before, Ben was relying on Keena to show him around as he searched for the perfect spot to propose. On the final day of their trip, Keena had one last stop in mind— a hike through one of her favorite running locations from college, Skyline Trail. Four miles into the hike, the perfect spot appeared amongst some redwoods. Ben told Keena he wanted a picture like their very first together, and to her surprise, he got down on one knee, she said, "holy shit!" quickly followed by a yes, and they were happily engaged.