Every Christmas, when Phil asked Jen what she wanted that year, she'd always say "a puppy." However, NYC living was no match for having a dog (or, dogs). So in jest, Phil would buy her a puppy of the month calendar each Christmas. Since then, on the first of every new month, Jen would flip the calendar to unveil a new pup. On July 1st, 2018, Jen flipped the calendar unknowingly to reveal "WILL YOU MARRY ME?" written inside. And the rest was history.