The couple met at a work trip in Chicago. Tom says it was love at first sight, Brittany does not remember the encounter. Tom, in love but not knowing if his feelings were reciprocated, goes back to working all the time. The casual hi, hello, goodbye at work with the occasional smile in the hall to the copy room continued. Fast forward a year and a half later, the world enters a pandemic, and naturally providing Tom with the perfect timing to make his move. For those who know Brittany, you know she is a germaphobe. Appropriately, Tom's first move is a photo in an airport of him in a mask traveling home from SF. Needless to say, this instantly won Brittany over. The next eight months were filled with text messages, paint by number challenges, taco nights, Zoom dates, and pretending to like the other person's shows on Netflix. Eventually (eight months later), Tom asked Brittany out on an in person date in Central Park. The tell tale sign the date was going well was Brittany allowing Tom to use her bathroom before they went to dinner. The first date was a success, and the rest is history. Over the next year Brittany and Tom were inseparable, learning to work, live and sleep in a NYC studio apartment.

Ok, a little background. For those who know Tom, he is carefree, unable to keep a secret, and not the best planner. For those who know Brittany, she is perceptive, type A, and knows how to get a secret out of Tom. This made planning the proposal nearly impossible. Tom came up with the perfect proposal plan. He wanted to recreate the couple's first date in Central Park. On their first date, Brittany planned everything including what the couple would eat, drink, and sit on. But this time he would plan the entire picnic. This is where things got tricky. Firstly, Tom couldn't remember the exact location of their first date in the park. He walked almost every inch of the 843 acre park before he finally found the hill where they had their initial picnic. Secondly, Brittany was determined not to be surprised. Let's go through a non exhaustive list of all the ways things went off plan. Brittany accidentally intercepted a message from Tom on the proposal plan that was intended for her mom, Faith. Tom tried enlisting Faith to get Brittany out of the apartment on the day of the proposal by planning a “shopping trip” to Bloomingdale's. That failed. Next, Tom tried making early dinner reservations. That plan was thwarted when Brittany called the restaurant to move the reservation. In a desperate final act, Tom coopted one of Brittany's work friends to distract Brittany. That actually worked. Despite all the hiccups, the proposal was everything the couple could have dreamed of. Tom was able to sneak out of of the apartment, leaving behind a note for Brittany to meet him in the park. They recreated their first date, but this time they left the park engaged.