Talk about fate! On June 1, 2018, Jimmy and Kelly met at the Harp in Boston. Neither of them were supposed to be there. Both groups of friends they were with had originally planned to go to different bars that night. God had bigger plans for them, and somehow, they both ended up at the same bar. Jimmy had been separated from his friends, and while he was looking for them, he caught a glimpse of Kelly, who was headed towards the bathroom. He immediately approached her and introduced himself. Kelly left to go to the bathroom after a few minutes of chatting with him. Jimmy told her he would wait by a post in the bar for her until she was out. Sure enough, he did. He waited much longer than Kelly ever thought he would. Kelly ran into another group of friends on her way back from the bathroom and talked to them for a while. To her surprise, after about a half hour of talking with friends, she looked over and saw Jimmy still waiting by the post he had told her he would be standing next to. When Kelly finally went back over to Jimmy and said she couldn’t believe he waited so long, he told her he would have waited all night if that’s what it took to have more time talking to her. Little did Jimmy know that would not be the last of the waiting- his patience is truly unmatched. Before leaving the Harp, Jimmy got Kelly’s number and told her he would love to take her on a proper date. He sent Kelly a message the next day saying it was nice to meet her and asked her on a date. Kelly waited a month and five days, to be exact, before eventually agreeing to go on a first date with Jimmy.

It’s safe to say that neither of them had ever been on a better first date in their lives. They went to Market Street in Lynnfield. They stopped at Yard House while waiting for their lane at King’s bowling, and ordered appetizers (one of almost everything they had on the menu). Kelly obviously schooled him in bowling. Jimmy and Kelly then went to Temazcal and sat by the fire pit and talked until they closed. Their night was filled with so many laughs, and they were so eager to see each other again. So eager, in fact, that they had their second and third dates the following two days. Then comes more waiting. Kelly had two trips planned. The first was to Australia for two weeks, and the second was to Florida for 8 days. Kelly left for Australia the day after their third date. Jimmy stayed up most nights just to be able to talk to Kelly, who was 14 hours ahead in Australia. She came home after two weeks, and was only home for 2.5 days before leaving for her Florida trip. Kelly went right from the airport to see Jimmy, and he asked her to officially be his girlfriend that day with some sweet gifts. Once she came home from Florida after 8 more days away, they could not wait to start creating more memories and spending more time together. Their relationship is as strong as it gets, and is filled with faith, family, friends, and so much love!

Even though the proposal wasn’t exactly what Jimmy had planned for so long, he blew it out of the park. Jimmy’s original plan was to propose in Austin, TX in April, while he and Kelly were there visiting her sister, Kayla, and brother-in-law, Austin. Little did Kelly know, Jimmy was secretly texting and planning with Kayla. The plan was to propose at a gorgeous observatory deck high above Lake Travis. Jimmy had booked a photographer, ordered flowers, and had planned it out to be a perfect day. Jimmy and Kelly have grown extremely close to each other’s families. Months before the proposal, Jimmy took Kelly’s parents out to dinner and asked for their blessing to marry her. Jimmy also talked to each of Kelly’s siblings about it before buying the ring. Kelly’s family was beyond thrilled that Jimmy would soon officially be a part of their family. Of course, Jimmy also spoke to his own family, and they all shared the same excitement. Plans changed when the pandemic forced Kelly and Jimmy to cancel their trip to Austin, TX. Jimmy did not want to postpone asking Kelly to spend the rest of her life with him. He spoke with his mother, Judi, and his sister, Jen, who both agreed that the proposal should not be delayed and the changing circumstances should not affect such a meaningful moment. Jimmy then talked to Kelly’s family members. He was trying to come up with an alternative plan, which was just as special as his original idea. Jimmy was looking into beautiful places in Massachusetts to propose and came across some places in Gloucester and Rockport. When he mentioned that to Kelly’s parents, Kelly’s father, Kevin, told him that he proposed to her mother, Kathy, at a jetty in Rockport. Jimmy loved the idea of proposing at the same spot as Kelly’s parents and knew that Kelly would, too.

Kelly’s family played a major role in setting up this day. Jimmy and her family had to be creative with how to get Kelly to Rockport and out of sweatpants during quarantine. Her mom, Kathleen, told them all she wanted them to take a ride to Rockport where they could walk around before having to “shelter in place” because of COVID-19. Kathleen then told everyone she wanted to take a family picture while there, to remember this crazy time “that would be in their kids’ history books someday.” Kelly and Jimmy agreed to go for this family walk, and dressed ready for a “family picture” to be taken. Kelly never suspected what was really about to happen. On April 5, 2020, Jimmy, Kelly, her parents, and Kelly’s brother, Kyle, headed to Rockport for their “walk.” When getting into the car, Jimmy made sure to sit on the right side, keeping the ring box that was in his pocket out of sight. Once they arrived, Jimmy grabbed Kelly’s hand and led her in front of her family and started heading toward the jetty. Kelly’s mother dared them to “walk over there and dance in front of everyone.” As Jimmy and Kelly were walking, Jimmy began telling Kelly how much she meant to him, how beautiful she was, how blessed he was to have her in his life, and that he could never spend another moment without her. As Jimmy continued to share all of his loving feelings, he began to drop down on his knee. In this moment, Kelly looked over to her family and realized what was about to happen. Once down on his knee, Jimmy then looked up at Kelly with a big smile and asked “will you marry me”, while holding the ring box upside down, with the ring facing the ground. Kelly instantly said yes. Although she never thought she’d cry when it happened, the happy tears started streaming.

Kelly’s mom captured the whole thing with her camera, while Kyle took a video on his phone. They ended up going for a short walk while they were there, then they headed home, eager to tell the rest of their families the news. When they got back to Kelly’s house, her brother, Kevin, had decorated the entryway and kitchen, with Kayla’s help and guidance. Jimmy and Kelly FaceTimed the rest of their family members and friends once they were home to share the great news. It was a truly perfect day neither of them will ever forget. Luckily they went to Rockport for the proposal when they did, because they tried to go for another walk there the following week, and the jetty was closed to all visitors. Talk about perfect timing!