One spring evening, Connor and Alex were at a fraternity/sorority social at UConn. Alex was by the bonfire when her friend suggested they go play Kan Jam. Connor was playing Kan Jam with his friend, and they decided they should be more social with their guests. As Alex left the fire, Connor and his friend were walking towards them to invite some girls to join a game. Connor and Alex teamed up, and haven’t lost a game of Kan Jam since. Connor and Alex reconnected at a tailgate the next semester. This of course, was orchestrated by Alex and her friend, Kristen, whom Alex had mentioned Connor to multiple times. Kristen strategically put Alex in Connor's line of sight, to which Connor then made the next step of walking up and starting a conversation. After many weeks of Tower's pasta bar dates, 2 semi-formals, and their first real date at Red Rock Diner, Connor asked Alex to be his girlfriend.
Some of you may know that Alex has been planning this wedding for quite some time, so it comes as no surprise that she knew the engagement was coming soon, mainly because she had explicitly told Connor that according to her timeline, it had to come before her graduation in May. Unsurprisingly, Connor did not follow her instructions and he ended up breaking his toe instead. In anticipation, Alex had painted her nails every week for about 2 months. However, she became relaxed in this routine and had given up all hope of being prepared for the proposal. Alex was now forced to wait and be patient; something that, to put it lightly, does not come naturally to her. Alex woke up the morning of June 17th to her car not starting, causing a fresh wave of stress. That night, she was weighing her options on how to get her car fixed, and Connor was suspiciously trying to downplay everything and convince her to not deal with it right away. That night, while they were watching their current Netflix binge, Connor suggested they go get Neil's Donuts (Middletown, CT: highly recommend) the next morning. Being her typical dramatic self, Alex defiantly said, "No, donuts are so fattening," which crushed Connor's dreams, because any other day she probably would have said yes. The morning of June 18th, Alex woke up determined to get her car running. Unfortunately, her phone wasn't charged, so she couldn't call AAA immediately in the morning like she had planned. She took Brewster for his morning walk, which took way longer than anticipated because he was super picky about his #2 spot. She got back to the apartment, dually annoyed that she hadn't been able to call AAA and she was now sweating from the unexpected 40 minute long #2-spot-search. Connor was up and dressed, which was odd because he usually slept late on weekends. He informed her he was going to get donuts, to which Alex replied, "Bring me back a blueberry." One last push from Connor, and he convinced her to go with him. She changed out of her now sweaty ~semi cute~ outfit, and swapped it for an athletic t-shirt she had gotten from her gym, sweat-pant shorts, and Birkenstocks (obviously with comfort as the main priority). As they were on their way home from Neil's, Connor "missed his turn," and they ended up passing one of their favorite restaurants that had recently closed down. Connor offered to pull in and check it out, and Alex replied, "No, why would we need to go there? I’m not getting out of the car." (Subconsciously just really trying to de-rail his plan.) Connor then suggested they eat their breakfast on the boardwalk overlooking the river, and luckily for Connor, that was an agreeable plan to Alex. Alex eventually noticed that Connor hadn't touched his donut, which she questioned and instead of answering her, Connor said he had to get something from his car (wink wink). He posed it as a just a regular, spontaneous gift, and Alex (being her typical gullible self) completely believed him. Connor showed her a scrapbook of pictures he had taken of all the places where they shared their 'first' moments (first kiss, first date, first place they met, etc). It wasn't until the last page, when Connor said he knew, "these first moments would be our last first moments, and the ring was really there all along," did Alex finally pick up that the moment she had been waiting for her whole life, was finally here. Connor asked her to marry him and obviously.... She said "YES!"
Connor purchased the engagement ring in March of 2022. With Alex's not-so-subtle-hints, he knew that the sooner he asked, the better. However, it was Connor's goal to make the engagement a surprise, which was a near-impossible feat given Alex knew the engagement was imminent. April and May were really busy months, with Alex finishing up Grad school and Connor...golfing, so the engagement was delayed. At this point, Connor still didn't know how he was going to ask the question, so the pressure was building, as the ring remained in his dresser. He knew that he wanted his and Alex's parents to be a part of this special day, but he soon learned that Alex's parents were leaving in June to visit family for the remainder of the summer. Just to add challenge, Connor broke his toe in May and was in a walking boot for several weeks, so any engagement idea he had that involved walking was no longer viable (so, all of them). The weekend of June 11th (the week before the engagement), Connor still had no clue how he was going propose. Alex was away for a bridal shower, so Connor was left alone to devise his plan. Suddenly, he had some inspiration, so he hopped in his car with the dog and the ring, and hit the road. He brought the ring to every spot he could think of in CT that he and Alex shared all of their 'first' important moments (first kiss, first date, first time saying "I love you"). Two photos of each spot, one with the ring and one without. Some were a little tricky, and possibly illegal, but anything for the shot. Connor spent the next week 'working' from home and crafting a scrapbook with all these photos he took. With help from Alex's dad, Jeff, he coordinated a surprise lunch for Saturday June 18th with both sets of parents. The day before the engagement, Connor drove to the spot where he planned to propose and planned out how he was going to get both him and Alex there, without giving away the surprise. Once everything was in place and nothing could affect Connor's fool-proof plan, Alex's car broke down the day before. So the morning of June 18th, she was planning on calling AAA. That morning, the usually late-riser Connor, was up at the crack of down to make sure she didn't call AAA. Instead, he suggested they go get donuts from their favorite shop in town, to which Alex oddly said "No". Luckily, she didn't take much convincing without giving it away, so off they went to get donuts. They left the donut shop to go home, when Connor 'missed his turn' and instead had to drive by Harbor Park overlooking the Connecticut river to get home. Here was another one of their favorite spots in town, where one of their favorite restaurants had unfortunately closed down. When Alex denied Connor's ploy to check out the closed down restaurant, Connor suggested they pull in and eat their breakfast by the water. It was the perfect day, high 60's and no clouds in the sky, so Alex took much less convincing with this suggestion. They found a bench to eat the donuts, but Connor hardly touched his. When Alex finished, Connor presented the scrapbook to Alex as a 'gift' and they went through the photos together. On the last page, all of the same photos were shown again, but now with the ring in shot. Connor got down on one knee and the rest was a blur, but she said Yes!