Caitlin and Chase have known each other since middle school. In high school they even had French class together. Caitlin will never forget Chase hiding under their French teacher's desk while two other students were arguing. For the rest of high school and into their early 20s, Caitlin and Chase had mutual friends and were around each other often at events. They talked at gatherings and occasionally interacted on Twitter, but not much beyond that. Not until 2020.

That July their mutual friend Paige decided to celebrate her birthday by going kayaking. Paige invited Caitlin. Tyler invited Chase. While Caitlin was busy talking with Paige and trying her best not to get her kayak stuck, Chase noticed her in a way he hadn't before. Caitlin was none-the-wiser while he helped her take pictures of the city lights on the water. A couple weeks later Paige shared with Caitlin that Chase said she was cute. Being completely oblivious, Caitlin assumed he meant it in "the way you think your friend is attractive but in a completely platonic friend kind of way." (to this day, Chase still makes fun of her for this). A couple months later, at Paige and Tyler's September wedding, Caitlin started thinking about Chase differently as well. Two weeks after that, Paige and Tyler (being the sneaky but well-meaning friends that they are) arranged for Caitlin and Chase to spend time together on their own. They stayed up until 5am talking and watching Fantastic Beasts. It wasn't long before Chase asked Caitlin on their first date: Mexican food and a drive-in movie.

For months, Chase told Caitlin that he was not going to involve any of her friends in the proposal due to fear they would somehow give something away. This turned out to be a big fat lie. For Paige's birthday, she asked Caitlin and other friends to join her for a night out at Bridge Park. She explained that Tyler would be working that night and so she wanted a girls night, asking that they dress somewhat fancy. They started with dinner at Urban Meyer's Pint House. While there, everyone acted normal. The chicken tenders were great. It wasn't until Paige and others started demanding Caitlin remove her Apple watch for pictures that things seemed weird, but Caitlin shrugged it off as Paige had gotten on her for wearing her Apple watch during "cute things" before. They arrived at Vaso and up the elevator they went. When they walked in and turned to their table, the real reason for them not wanting her watch on became clear... Chase was waiting for her at the rooftop with roses, many of the girls' husbands (including Tyler who took pictures), and a beautiful ring. They ALL knew and kept the best secret. The night ended with a duo celebration of Paige's birthday and Caitlin and Chase's engagement at Pins.

Chase proposed three years to the day after going kayaking together and it was absolutely perfect.