Colleen & James met in Wildwood, NJ where both their families owned vacation homes. They were about 3 and 5 years old the first time they laid eyes on each other. James became very close with Colleen's brother Danny, and even though James & Colleen grew older and led different lives, James kept in touch with Danny over the years. Through that friendship, James and Colleen met again and rekindled their relationship in their 20's.

On August 28th 2021, James & Colleen arrived in Wildwood to spend a romantic weekend together. James planned on having a plane fly over the beach, asking Colleen to marry him. But the stormy weather changed those plans... The event was canceled and rescheduled for the next night, but the rain continued to pour. Right before the plane was scheduled to fly over the beach where James & Colleen spent many summer together, the sky opened up and a beautiful sunset appeared. James & Colleen walked down to the water where James got on one knee as the banner flew overhead – reading "COLLEEN, WILL YOU MARRY ME?"