Jeff and Anna attended Mike (the Officiant) and Brittany's wedding and out of sheer luck, they were seated across from each other. And due to not knowing many people at the wedding, spent the whole night hanging out. Jeff happened to be in town for a few more days and invited Anna to dinner the following night. Jeff was so charming at dinner that Anna agreed to go to see the Buccaneers play the following night for Monday Night Football. Anyone that knows Anna, knows that she's a huge sports fan. That went so well that they planned two trips to visit each other. First up, Anna to Boston and then Jeff back to Florida. Slow to get started, the two eventually got in the routine of traveling back and forth for weekends with each other. Enjoying each other and everything their two cities had to offer. While it was hard to be apart, it was really fun having two great places to explore. It was all fun and games until Covid. What was supposed to be a quick visit to Tampa for Anna's birthday turned into a 100 day stay with only a carryon for Jeff. Jeff took to the Florida lifestyle….and living with Anna pretty quickly. That fall, Boston lost two great icons and 6 Super Bowl rings with Jeff deciding to move to Tampa shortly followed by Tom Brady. Despite both working from home and being together 24/7, the two still enjoyed each other very much and decided to take the next step. Jeff planned a weekend getaway to Dunedin, a town they both love. Jeff proposed at the Fenway Hotel (no affiliation but GO SOX), the same spot you will watch them marry each other on 12/1/23.