Jenny spent the first month of summer 2019 trying to figure out when she could get over for a visit to Nantucket, her favorite summertime scene. At the last minute on a July Friday, her friend Kristina texted, asking if she wanted to head over to the island to visit their friends Lilly and Rachael and enjoy a night away from their bartending jobs on the Cape. Ever the hostess, but having to work a double shift at the Chicken Box that night, Lilly suggested the girls meet up with her roommate Timmy and his best buddy Billy who were going to be out on the town that evening. The four of them met up, had a blast singing, dancing, and laughing the night away, and all ate delicious seafood together for lunch the next day. After Billy won her over by sharing his tuna poke, Jenny was excited when, before catching the ferry back to Hyannis, he asked her to come back to the island to have dinner together the following weekend. She had so much fun on their first "real" date at Ventuno, she continued to return to Nantucket for the next eleven weekends in a row ... and the rest was (commuter book) history!