Lili and Nick first met at age eight during a new student orientation day at King and Low Heywood Thomas School. For Nick it was love at first sight. For Lili it would take a bit more convincing. Luckily, the 3rd grade Nick Nickitas was up to the task, and quickly Lili and Nick starting dating. This fledgling romance lasted until Lili called Nick and said that she didn't want to be his girlfriend any more. Being the precocious 10 year old that he was, Nick told Lili that this would be the biggest mistake of her life. 

It would take 15 more years for Lili and Nick to come back together. 

Nick and Lili finished elementary and middle school at KLHT and went their separate ways to New Canaan and Greenwich High School respectively. After their formative college years, Lili and Nick would each land in New York City to start their careers in advertising and financial services.