Riley had his heart set on proposing where it all started for him and Jess: Rhode Island. It was their happy place, where they met and fell in love. They both attended school at the University of Rhode Island and met at a sorority and fraternity gathering off-campus in Narragansett. On their first official date as a couple, Jess & Riley walked the streets of Newport on February 14, 2016. It was 1 degree out, but they toughed it out to explore their favorite place. On their date, they stopped on the rocky shoreline of Ocean Drive to snap a moment. Fast forward 4 and a half years later: Riley and Jess had plans to get together in RI one weekend with college friends. Riley thought the timing was right. Little did Jess know, this was months in the making. Riley has been custom making the ring and hid it in his sock drawer up until that weekend. It had been a few months since they've been to Newport, so Riley & Jess decided to get a hotel room the night before the party to spend some quality time together. Riley mentioned to Jess he wanted to take her to a special place in the morning. Jess got dressed up (because she's always ready for a picture-perfect moment) and they set off for that location. It was a little overcast and raining, but as soon as they parked, the rain stopped! That's when Jess realized Riley brought her back to the same spot they went to on their first date. The rocky shoreline where they took a picture on that cold February morning where it all started. Jess could tell Riley was stalling and all of a sudden we see someone in the bushes with a camera (shout out to Layla!). That's when he got down on one knee and popped the question! Riley then took Jess to her favorite seafood restaurant for lobster, walked around downtown, adventured to Narragansett to have drinks on the ocean, then celebrated the night away with college friends. The weekend ended with celebrations with Jess's home friends. It was a weekend they both will never forget.