On a frigid January night, Kaileen and Taylor first crossed paths when walking between the Student Union and Johnson Art Center at Carthage College. Kaileen introduced herself and immediately stole Taylor's heart with her warm personality and big curls. Kaileen would learn that Taylor was in Student Government and found something that they could both talk about ... getting funding for her student organization, Draft. Kaileen and Taylor would first meet to talk about Draft's budget, but this quickly turned into lunches, playing pool and watching funny Vine videos. It would take several months before either realized their mutual affection for each other.

Kaileen and Taylor grew closer together over their Freshmen and Sophomore years in college until November 16th when a spark turned their friendship into something more. During a cold rainy day Taylor approached Kaileen with an umbrella to shelter her from the rain while she played her saxophone for pep band. The two would spend the afternoon working on homework, although Taylor would get little done as he was more interested in spending time with Kaileen even if it meant watching her outline images with hundreds of dots. After Taylor offered to pay for pizza for the two of them, Kaileen started to piece together all of the little hints throughout the day. Both wouldn't reveal their feelings for each other until later that night while watching Horrible Bosses when they first held hands.

In the Summer of 2018, Kaileen and Taylor traveled with a group of friends to Japan. Taylor was in charge of organizing the trip and used the opportunity to orchestrate the most romantic proposal. Unfortunately the best-laid plans of mice and men often go awry. Taylor had entrusted his brother Chad with ferrying the ring to Japan so Kaileen would not discover it, but Chad had forgotten the ring at home. Shocked and frustrated by this discovery Taylor had devised a new plan while guiding everyone between Osaka, Kyoto and Tokyo. The new plan was to propose to Kaileen at the Love Shrine of Tokyo (Tokyo Daijingu Shrine). He convinced Kaileen to visit the shrine by pointing out the shrine's purple banners (Kaileen’s favorite color). Without the ring, Taylor decided to write out his proposal on an Ema (Shinto wish/prayer tablet) and had Kaileen read it while he got down on his knee. Kaileen was ecstatic and even got a laugh out of the whole situation.