It all started on Black Friday of 2014 at a cozy Irish pub in Chicago by the name of Fado. Kayla and her sister, Maggie, were downtown for the weekend Christmas shopping with family, and after a long day on Michigan Ave., were searching for a properly poured Guinness. Chris, after spending time with family in the suburbs had come to join his roommate, Conor, and several other friends who were in town for the holiday. Kayla caught Chris's eye almost immediately from across the room; however, he didn't quite have the guts to walk up and introduce himself out of the blue. Luckily, a friend of Chris's (Kevin) who had a bit more courage that day was not quite as reserved. Surprisingly, not only did Kayla and Maggie welcome Kevin's intrusion, but accepted his invitation to join the boys' table. Kayla, Chris and the rest of the two groups introduced themselves and began to strike up conversations. Not long after, Conor, looking for a change of scenery, suggested the group walk down the street in search of karaoke - Maggie was skeptical, but Kayla assured her there was nothing to worry about because at this point she was convinced the boys were just a bunch of nerds (she wasn't wrong)!

After changing venues, Chris was eager to make an impression on Kayla so he convinced her to join him in singing his favorite number by the Backstreet Boys. Little did Chris know, Kayla doesn't enjoy singing (especially in front of other people), but she obliged and may have even enjoyed it a little bit! After the duet, the two continued talking late into the night until Kayla had to return to her hotel, so they exchanged numbers and went their separate ways.

The next day, the two began texting and Chris probably thought that a first date was all but guaranteed; however, Kayla wasn't so sure about this random guy she met during her night out in the city. It would be 5 weeks before they would see each other again, when Kayla invited Chris to join her and her friends out one night in the city. At this point, Chris was finally able to convince her to join him on a true first date the following week - and the rest is history!