Sheldon and Olivia met via a mutual friend who is currently a member of their wedding party. She introduced Sheldon to Olivia's Instagram, where he proceeded to slide into her DMs. After a few weeks of talking, Sheldon asked Olivia out on a lunch date. During their first date, they spent several hours getting to know each other. The day quickly turned into night and the rest was history. They have been inseparable ever since.

On March 18th, 2022, Sheldon and Olivia went on a date to Negril Village in NYC. Olivia has been trying to get a reservation at this restaurant for the past two years. However, the restaurant was closed due to Covid. During the train ride into the city, Olivia noticed that Sheldon was nervous and appeared to be fidgeting. Eventually, Olivia asked Sheldon if he was going to propose, to which he answered No. It was not until after dinner and they were on our way home that he drops to one knee and asked Olivia to marry him. To which she responded, YES!!