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Howley and Kristen initially met through mutual friends after discovering they had shared common interests in exploring new places, foodie adventures, and video games. They continued to play video games together with their friends, and eventually decided everything was more enjoyable as a duo. They held a long and healthy relationship for 7 years.

When visiting the winter wonderlands of Québec, Canada, Kristen jokingly exclaimed it would be a wonderful idea to get engaged while surrounded by a snowy rose garden. Howley informed her that he did not bring the ring he had once promised he would entrust to her. Nonetheless, they ventured through snowstorms together and enjoyed an abundance of joyous memories trying Canadian delicacies such as poutine and maple taffy, and ice skating under falling snow with family. When stopping to take a picture under the largest Christmas tree, Howley got on one knee and asked, “Will you marry me?”