The story may be slightly different depending on which one of us you ask, but it all started at team drinks while Sydney and Jeff were working at Tough Mudder. A bunch of employees started an intramural soccer team that Jeff and Sydney had joined, and they were both playing in a game that evening. After showing off their soccer skills, everyone migrated to a bar in downtown Brooklyn for some drinks. As the night was winding down, Sydney quickly realized that all of her colleagues lived in Brooklyn...except one. So, Sydney asked Jeff if they could ride the subway back together to Manhattan later that night. On the trip home, Jeff started doing what he does best, teasing Sydney about anything and everything. Syd's response was to firmly let Jeff know that she hoped he was nicer to any girls that he may be trying to hit on (seems only fitting if you know her mom's response when her dad proposed). Once they made it back to the city, they made a quick pit stop at Sydney's favorite pizza place, Joe's Pizza in the West Village, which started a pizza tradition for many dates to follow...and the rest was history.

Jeff and Syd were planning a trip to Florida in early November 2020. However, Sydney was unaware that for the two months prior Jeff had been making up excuses to sneak into Manhattan to pick out a diamond and custom make an engagement ring. As their departure date got closer, it became clear the ring was not going to be ready in time for Jeff to pick up before they left. Jeff's diamond guy (straight out of Uncut Gems) assured him that the ring would make it to Florida safely if he shipped it, and with no other choice, he agreed. Jeff tracked the package obsessively and knew the minute it would arrive at the house. When the delivery truck was only minutes away, he made up an excuse to get Sydney out of the house, got the package, and hid the ring. Once the ring arrived safely, Jeff shared the news with Sydney’s family on her mom’s birthday, over a week before he planned to pop the question. Her parents and sister put on their best poker faces and kept the secret the entire time, and on November 7th, Jeff popped the question at the beach. With plenty of wind and tears, Sydney said yes! They were greeted back at home by Sydney's immediate family and the perfect intimate celebration.