Ryan and Caitlin's story begins in 2013 at Custom Ink where they both worked as artists. Ryan was the last-minute trainer chosen when a few internships (including Caitlin's) turned into unexpected full-time jobs. Their friendship immediately clicked during training and continued to grow over the next 2 years as they found themselves spending a lot of time together professionally. They continued to remain close, even sparking some rumors they were secretly dating since they always seemed to be together. It wasn't until late 2015 that things took a turn. On multiple occasions, Caitlin and Ryan would accidentally stay late at work, having lost track of time talking. Caitlin realized the days Ryan wasn't working were her least favorite days. Ryan found himself inviting Caitlin to events outside of work (Caitlin thought they were pity invites). Finally, Caitlin realized she might have a crush on Ryan - a crush she could never act on since they worked together. Luckily for Caitlin, Ryan had a different idea. He bluntly told her over drinks that he felt something and that it was worth taking a chance on. Both of them quickly realized that taking that chance was the best decision either of them had ever made.

After about 3 1/2 years together, Ryan had planned one of his special dates as a Christmas present for Caitlin. On these special dates, he would often create a multi-location, all-day date, complete with a printed out itinerary. This particular date was planned on the same day that Caitlin had evening plans with a group of high school girlfriends, so an itinerary, Ryan claimed, was definitely necessary to stick to. Caitlin, genuinely in the dark as to what exactly was happening, was thrilled that Ryan had pulled together such a thoughtful list of places they had frequented when they first began their relationship. Starting at a coffee shop they would go to every Sunday, then heading to the winery they had their first date at, followed by several other locations that held deep meaning. Caitlin wondered for a second if this date was special, but quickly realized that, no - he would never propose and then expect her to go to a girl's night, right?!? They found themselves at the second stop of the day - Barrel Oak Winery, a longtime favorite of Caitlin's and where they had shared their first date. Upon arrival, Ryan mentioned he was interested in looking at the loft before they got their wine. At the top of the stairs, Caitlin received the shock of her life to find her and Ryan's family waiting. Ryan had been planning this elaborate proposal for months. Honestly, Caitlin blacked out from shock. Luckily she has a video that still makes her cry every time she watches it. As for the girl's night? Ryan is very cool. Everyone was in on it and all showed up for an impromptu engagement party. Best date ever.