It started with a girl who decided to go to college halfway across the country. In the freshmen orientation class, she was paired in a group with this same, goofy, shy guy for every activity. It turned out; he was friends with one of her friends that she had every class with during freshmen year. This friend decided it was time for them to meet. Despite being with other partners when they met, the two instantly clicked to the point that he introduced her to his family during the week that everyone's family came up to visit during that first semester. During this meeting, his mother called it that they would end up together at some point. She was ultimately correct and here we are, nearly nine years later.

After many years of hinting, Kyle finally made the decision and promised to propose before Valentine's Day 2021. However, it was not nearly that simple. In typical Kyle fashion, he waited until time was almost up to buy a ring and ended up having to buy one nearly two sizes too big. It then took not one, not two, but four attempts for him to finally propose as each plan accidentally got foiled by some external factor. First, he was going to surprise Izzy with breakfast in bed and knowing she would not be paying attention, was going to slip the ring casually with her breakfast. However, the day he planned this, he forgot she was going to be up early for work, so she got up before him and spoiled his plan. He was determined to try again the next day. Kyle wanted to go out and get something special to add to it since this was now the second try. Unfortunately, his car would not start. He got frustrated and gave up at this point with the whole breakfast idea. For his third attempt, Kyle was going to take Izzy out for dinner and go for a walk afterwards. Despite his newfound determination to finally propose as the deadline was quickly approaching, a snowstorm hit foiling his plans yet again. Valetine's Day then came and went. On February 16th, Kyle finally proposed. He had been talking with Izzy in their room and were discussing where they were in their journey together and where they wanted to go. Kyle, in his infinite wisdom, made Izzy pause mid-sentence to go and grab the ring from his desk. He walked back into the bedroom to her laughing hysterically at him being so obvious in what he was up to. But finally, he was able to ask the question and she said yes.