On the evening of Wednesday April 29th, after relentlessly watching the NB City Council live feeds, Grayson learned that Newport's beaches were closing May 1st due to Gruesome Newsom's COVID state orders. Grayson had originally planned to propose to Amanda on the Newport Peninsula beach the following weekend. Luckily, he had just spent the day with his photographer, Danielle Determan, at the proposal location walking through the following week's plan. On the morning of Thursday April 30th, Grayson knew that today was his only chance to keep his original beach proposal plan. He texted Danielle in hopes that she was available to photograph the event that evening. After she quickly replied "yes", his next step was asking Amanda's parents for their blessing. Grayson called Tom and Phyllis who were across the country on their Great American Loop adventure. Phyllis and Tom were elated and all three shared tears of excitement! Grayson's biggest hurdle was- how to get Amanda to the beach before sunset on a Thursday night? He enlisted her best friend Casey Lockey for help. Grayson and Clayton Scheulke (Casey's boyfriend) had plans to ride bikes together around the Back Bay that afternoon. Casey was working from home due to the stay at home order, and as soon as Grayson arrived to their place he broke the news about his plan. Casey immediately texted Amanda and asked if she and Grayson wanted to meet at the beach that night to watch the last sunset with her and Clayton before it closed. Amanda was reluctantly on board because they had all just hung out the night before for Tootsie's 6th birthday. As Grayson and Amanda arrived at the beach, the sun was starting to set and Casey and Clayton were no where to be found. Grayson asked Amanda to walk down to the water with him, and upon returning to their towel he got down on one knee. Danielle was there to capture the entire moment organically. After an emotional speech, Grayson asked Amanda to marry him and she said YES!