In May 2018, Kathleen had just completed her 3rd year of pharmacy school at Dalhousie University. Alex was doing a Master's in Mechanical Engineering at Dalhousie at the time. One of Alex's closest childhood friends, Casey Donovan, was also a pharmacy student at Dalhousie and he had just completed his 4th year. On May 19th, Casey invited Alex along to a house party for pharmacy students which Kathleen was also attending with some of her friends. Alex and Kathleen did not interact at the house party, but the party eventually moved to a night club called the Toothy Moose. Alex and Kathleen both grew up in Miramichi, NB, and Alex had been a classmate of Kathleen's brother John in high school. Alex recognized Kathleen as being John's sister and started talking to her. They talked about John, summer plans, and Kathleen even appeared to be interested in Alex's Master's research, which was highly unusual. Eventually, Alex suggested that they meet for a coffee sometime and they exchanged phone numbers. On May 21st, Alex and Kathleen had their first date when they met for a coffee at the Starbucks on Spring Garden Road in Halifax.

The Toothy Moose is not a very classy establishment; it's a rather dubious place that you likely wouldn't want your daughters to go to. Alex and Kathleen are both rather reserved and are certainly not big partiers or club-goers, so the fact that they met at the Toothy Moose night club is pretty amusing. They have not been back since that night.

In September 2023, Kathleen and Alex travelled to Vancouver for the wedding of their friends Gaithre and Kishor. Since they rarely get the chance to visit that part of the country, Kathleen and Alex decided to make a vacation out of it and stay for an extra week after the wedding. They spent a few nights in Vancouver and the rest of the time was spent on Vancouver island. They decided to visit a town on the west side of Vancouver Island named Ucluelet, near Tofino. This picturesque area is right on the Pacific Ocean and has beautiful hiking trails, coastline, beaches, and old-growth forest with massive, ancient trees. On September 18, Kathleen and Alex decided to hike the Wild Pacific Trail in Ucluelet. They came upon a clearing looking out on the rocky coastline and the raging surf of the Pacific Ocean and Alex suggested that they get a picture. Alex set up a tripod with his phone, but instead of pressing the button to take a picture on a timer, he started recording a video. He then got down on one knee and asked Kathleen to marry him, to which she exclaimed "Yay!" and threw her arms up in the air, followed by a "Yeah!" as she eagerly snatched the ring out of the box and jammed it on her finger. After an almost 5-and-a-half-year relationship, Kathleen and Alex were engaged.

Unfortunately, Alex had not done a very good job of hiding the ring box in the days leading up to the proposal, so the proposal did not come as much of a surprise to Kathleen. Alex had hid the ring box in his toiletry bag, thinking that "she will never look in there!". Alas, Alex had brought his toiletry bag into the bathroom and forget to zip it back up one evening as they were preparing for Gaithre and Kishor's wedding. Kathleen went into the bathroom to take a shower, and then saw the ring box sitting in Alex's toiletry bag. While trying not to laugh, she confronted Alex about what she saw. Seeing as they were about attend their friend's wedding, Alex did not see it fit to propose in that moment, so he told Kathleen that what she had found was the box for his retainer. Since most retainers do not come in velvet boxes, Kathleen was not fooled but Alex stuck to his story until he proposed a few days later.