It was May 2019 and Caili was swiping through a dating app called Hinge. After swiping left (‘no’) on many profiles and ready to close out the app, one profile caught her eye. She hearted (‘liked’) this profile with the hopes that it would be a match. Soon after, Caili received a notification from Hinge saying that she had a new match and message! When Caili opened the app she saw the guy from the profile she liked (Rob!) messaged her saying “hey Caili, how’s your Friday going?” …and that’s all it took! After a few months of dating during the summer, the couple took a brief hiatus only to reconnect on ANOTHER dating app called Bumble (some would say that it was meant to be). Since the second ‘match’ in December 2019, Caili and Rob have been inseparable. Not even a global pandemic could prevent their love from growing stronger. Two NYC apartments and one cute fur child later, they are now preparing to say “I do!” to a lifetime of love and happiness.

On Friday June 24th, Rob made a “dinner reservation” at Grand Banks, a restaurant they wanted to try for months, before they drove down to the Jersey Shore. Caili really wanted to go to the Shore on Thursday that week, which they normally do during the summer. However, Rob said he needed to go to a client meeting in western New Jersey on Friday and could not leave for the Shore until afterwards (this was initially a lie, but ended up being true!) At 5 pm, Caili should have known something was up when Rob was home, packed and ready to leave right on time (for once!). Caili and Rob drive down to Tribeca, found street parking and walked towards the restaurant. As they walked towards the restaurant, they took a minor detour down Pier 26 because Rob suggested it was the perfect place to get “content” for Oakley’s Instagram (@Oakleystateofmind). At the end of the pier, Caili tries to adjust Oakley in front of the World Trade Center to get the perfect photo. While Caili is starting to take photos, a random photographer approaches Oakley and starts taking photos of him while saying how cute he is. Caili engages in a full conversation with this random woman and asks if she could email them the photos so they can add them to Oakley's Instagram. Little did Caili know, Rob was positioning himself behind her on one knee. Rob taps on Caili’s shoulder, interrupting the photoshoot, which caused Caili to turn around mid-shot to Rob down on one knee asking for her hand in marriage. Completely surprised and fighting off tears of joy, Caili said yes! After the proposal, Rob planned a number of surprises for Caili that weekend. First, Caili’s parents walked towards them and surprised Caili on their way to City Winery to get a celebratory drink. Then, Caili was surprised to see her Aunt and cousins in front of City Winery. The evening of surprises ended with Caili’s brother and best friend from home sneaking up behind her as she sips her vodka soda. After the celebratory drink with surprises, Rob’s family joined Caili’s family in celebrating the couple’s engagement at Grand Banks for dinner! The surprises didn’t end there! The next morning Caili and Rob were getting ready to have a few friends and family over for bagels to continue the celebration. Caili kept telling Rob that she needed to call her cousin John Ryan to share the exciting news. In the middle of asking Rob (again) to FaceTime her cousin, all of sudden there is a knock on their apartment door. To Caili’s surprise, John Ryan, his wife Maddie, and their three little girls were there! Rob ended the weekend with a surprise engagement party, at Cask Bar (where they had their very first date) with the help of both families and friends! To say it was the best weekend is an understatement.