In January 2013, Kyle gave a mutual friend 2 free flight passes so that she and another friend, Megan, could go to Las Vegas for a long weekend. After Kyle’s own travel plans fell through, the mutual friend invited Kyle to tag along to Vegas. Megan was skeptical that this random guy was now going on her girls trip. Who was he? Was he a secret love interest of her friend? Was Megan now going to be the third wheel? So many questions. Right before the trip, the trio decided to go out for sushi so that Kyle and Megan could meet. Needless to say, Kyle was more excited to go on the trip after that dinner. While in Vegas, Kyle and Megan would stay up late talking about shared interests and had a running joke that they were there to get married, having pretend bachelor and bachelorette parties, and even stopping into the Little White Chapel to stage wedding photos (they were denied). At one point, a tipsy Megan left Kyle a voicemail looking for her “Hubs” in the casino and the first “love you” was recorded. Kyle still has this voicemail to this day.

A week or so after the Las Vegas trip, the Patriots were playing in the AFC Championship game. Kyle and his friend had planned to watch the game at Hooters like they did the previous year in hopes of a repeat win. Kyle’s friend could not make it that year, so he decided to ask Megan to watch it together, remembering that she liked football. When the awkwardness of asking a girl on a date to Hooters outweighed the fear of superstition, Kyle asked Megan if she wanted to go to Buffalo Wild Wings to watch it. Ultimately, the restaurant was packed and they ended up at Hooters anyway...and the Patriots lost. For years to come, Kyle would dispute that this meetup was intended as a date (out of embarrassment) but has since conceded to the idea that it was in fact their “first date.”

For Valentine’s Day 2013, Kyle took Megan to NYC as their first overnight getaway together. They stayed in a hotel right next to Times Square, went ice skating in Central Park, visited the top of the Empire State Building and ended the night in an Irish bar. Nine years later, Kyle planned another getaway to NYC for Valentine’s Day 2022, this time for a proposal! Under the guise of visiting NYC for Moulin Rouge on Broadway, which Megan was dying to see, Kyle planned out the events leading up to the proposal to be reminiscent of that first trip. They would stay at the same hotel, ice skate at 30 Rock, go out for a nice dinner before the show and even have a nightcap at an Irish bar. The night went perfectly. The following morning, there was a heavy, picturesque snowfall in NYC. A storm that closed not one, but two scenic areas on the walk to brunch where Kyle was hoping to pop the question. As they continued to walk in the snow, Kyle snuck a peek in his jacket pocket and realized he had grabbed the wrong ring case. He had forgotten he switched the ring into another case. The ring was at home. Megan was oblivious to all of this, but did ask multiple times at brunch if Kyle was sick because he looked like he had seen a ghost. Kyle toughed it out the rest of the day and as soon as they reached home, in time for Super Bowl LVI to start, he grabbed the ring and popped the question in their living room with their two cats by his side.