They met while working in New York City. Tamara was Will's trainer on his very first day. They were both seeing other people at the time, and became friends on social media. Years later, and sans partners, Tamara was invited by one of her friends to see an improv show in Times Square. Low and behold, it turned out to be Will's show, in which he was starring. At the end of the performance, Will approached Tamara to reconnect, and as everyone was chatting, he would pretend to walk away for a few seconds to talk with other people, and then casually circle back to Tamara. His intention was to be casual about his interest in her, but it was obvious. At the end of the night he promised to write her a hand-written thank you note for coming to his performance. Tamara reached out to him regarding her thank you note the next day, and instead, was propositioned with a date. She is still waiting for her hand-written note.