In the December of 2017, Sierra lowered her age range on Tinder by one year. It was this fortunate gesture that led her to matching with Ryan. They met at their graduate school's end of semester writing retreat, although Ryan was too shy to say "hi" first. They eventually got their shit together and went on a proper first date at the Moan and Dove, a bar in western Massachusetts. Ryan went away for winter break, but the two of them stayed in touch. When the semester started back up again, the two of them went on a few more dates and decided to make it official.

After studying abroad in Rome in 2012, Sierra always dreamed about showing the city off to her loved ones in the future. About two years ago, she thought that her 30th birthday would be the perfect occasion for a return trip. Midway through the vacation, Ryan and Sierra trekked up the Janiculum Hill to admire the view of the city. After a while, Sierra turned to Ryan and said "Ok, what do you want to do next?" and Ryan said "Get married!" Sierra had lunch on the mind, but this worked too!