Ryan and Allison first met on Hinge, a dating app, where Ryan correctly guessed Allison's "2 Truths and 1 Lie" prompt (he was the only one to guess correctly...ding ding ding, we have a winner!). They instantly clicked and spent the week before their first date getting to know one another via text. Ryan went above and beyond planning their first date, keeping the main details a secret from Allison. He gave her the following hints: our date has 2 parts, the restaurant is "untraditional," and for the second part we'll have to wear a hat and a glove. Ryan brought Allison to N TO TAIL, a Koren BBQ restaurant in Portland, where they spent 3 hours talking over dinner and drinks. The second part of the date was mini-golfing (or extreme mini-golfing you might say- since they were wearing golfing visors and gloves). They spent the whole night laughing and enjoying each other's company. They knew at the end of this date that they had something truly special. Following this night, Ryan and Allison spent pretty much every day in each other's company falling more and more in love...

Allison and Ryan realized early on that they had found the person they wanted to spend forever with. During the next two years, they truly grew as a couple. Between Allison passing her board exam to become an occupational therapist and getting her first job in the field and Ryan getting a job in IT at the Shipyard so that he didn't have to paint submarines anymore, they were each other's biggest cheerleaders. Ryan finally got Allison to watch every episode of Game of Thrones and The Office, and Allison got Ryan to try many new foods (anyone that knows him knows that he is the world's pickiest eater). They spent weekends driving around in Ryan's car with no destination in mind, wake surfing the days away in summer, spending quality time with friends and family, and taking their French Bulldog, Luna, for walks against her will (she is the laziest dog ever). During quarantine, they made the most of their time by planning date nights at home, adopting Wesley (the sweetest orange kitten from Aruba), developing a taste for gin and tonics, becoming incredibly competitive with Wii Bowling, and realizing that there is no one else they'd rather spend their time with than each other. Their love for each other continued to grow as the years went on and Ryan began looking for "the ring"...

Ryan found the ring and began planning how and when he would propose to Allison. With the help of Allison's sister, Erika, they developed a plan to convince Allison that they would be doing a photoshoot to help Erika practice her couples photography. On the morning of the proposal, Allison was surprised that none of her family members were kicking her out of the bathroom and she took her sweet time getting ready. Erika must have known Allison was getting suspicious because she said "Al, you need to hurry up or Ryan isn't going to want to do this anymore." The photoshoot started on the dock at the lake and ended on the beach where it all went down. While Allison was busy picking a flower, Ryan got down on one knee. Allison turned around and in complete shock immediately dropped the flower. Ryan told her there's no one else he'd want to spend his life with and would she marry him? Of course, Allison said "yes!" Later, Ryan would find out that Allison had picked that flower to turn around and fake propose to him to make for a good photo, but he beat her to it. The two celebrated their engagement with a trip to Stowe, Vermont where they went zip lining, nature touring, beer tasting, and spent time talking about the life they would build together.