The first day they met, Tim had started as a new manager at Galley Beach and Alison had just come back to Nantucket island and popped in to see if she could get her old job back from last year. When Alison left the meeting with her schedule in hand, Tim asked with interest "Who was that?" to which he was promptly told "No Tim, we like her." Clearly, he didn't listen, and honestly she was just as bad.

It was Date Night in August. Alison thought it was a little odd to go out since it was also the night Tim's family was arriving in town. But he had assured her it would be best to give the family space to unpack and get the kids to bed. After dinner they walked down to the NYC's docks to "drop off some boat keys." A very effective ruse, he surprised her not only with a sudden proposal but a bottle of champagne on ice hidden in the yacht club's launch. The perfect end to a wonderful night.