It all started because one of Kennedy's friends was dating Kevin's roommate. She had insisted over and over that Kennedy & Kevin would be great friends "if not more" and that they simply had to meet. She invited Kennedy to be Kevin's date at one of his fraternity date nights- a date night that Kevin was not planning to attend given many unsuccessful set-ups in the past. After telling Kevin she had already invited Kennedy, Kevin decided to bite the bullet and go on the date night instead of having to tell Kennedy he wasn't interested. Thank god he did, because they went bowling that night and had more fun with each other as complete strangers than they had ever had on a first date. They competed for the 'worst bowler' award, chucking the bowling ball for each other in the worst way possible if the other wasn't looking. Kennedy bought chili cheese fries for them to split and that's when Kevin started to fall in love. Kevin invited Kennedy to the next date night and the next one... and the rest is history!
"I wanted to wait until I was sure it wouldn't happen before I said anything, but I had a weird feeling you were going to propose to me this trip" Kennedy said to Kevin an hour before he was going to do just that. After somehow calmly diffusing the situation at hand, they walked back upstairs to the Sea Grape Inn in Longboat Key, Florida where the rest of the Rand family was getting ready for "family pictures" on the beach at sunset. With only Kennedy's parents (and Kevin's parents, who were anxiously waiting in the Inn's parking lot) privy to what was going to transpire, corralling Kennedy to walk down to the beach with Kevin first proved to be more difficult than anticipated. But nonetheless, they began their walk towards an everlasting memory. With each step towards the shore, many things were happening in the background. Kennedy's sisters were finally let in on the secret plan, Kevin and Kennedy's parents met for the first time, the champagne was put on ice, and the groups headed down to the beach closely following the soon-to-be engaged. As the couple arrived where the water meets the sand, Kevin, with his heart pounding, pulled out 7 love letters he had been writing for the past 7 days, with his justification for such a grand gesture being "just because". After Kennedy obliviously read through the first few letters, she made it to the last few and the moment began to sink in. As she finished the letters with tears in her eyes, Kevin said "and there's one more thing I forgot to write down" as he got down on one knee. After an eager yes, the family (with random onlookers) cheered as Kennedy turned to finally notice them. After a quick toast back at the house, the family (without the random onlookers) went out to dinner at one of their favorite restaurants in town.