Allie and Will joined Teach for America after college, and were both placed in Baltimore. Will grew up in the area, so it was a homecoming for him, but Allie came from San Jose and had never lived far from home. One of the first days of the program their corps volunteered at a food bank - it was there Will noticed Allie. As people spread out to pack meals he made sure to find a spot near her, and casually asked where she was from. "San Jose, really! Do you like the Sharks?" "Yeah!" Will was ready to name all their players and impress this girl, but that proved unnecessary. Besides, Allie probably wouldn't have known whether he was right. The corps eventually traveled to Philadelphia for their summer-long training, where Allie and Will got to know each other better. It was a hot summer, and these two were a breath of fresh air for each other. Allie remembers Will always asking how she was doing when they crossed paths in the dining hall. Will remembers wandering the dining hall pretending to look for food. Those days were busy and there wasn't much free time, but one night Allie and Will went out with some friends for a night on the town. They had fun, and at the end of the evening Will offered to walk Allie back to her room. In gentlemanly style he gave her a hug and wished her a good night. Some minutes later, back in his room, Will got a text. "Just a hug?" He ran with haste, and the rest is history.

As a child, Will made many visits with his mom to Longwood Gardens, a lush estate with magnificent gardens and architecture. In particular, he loved the Italian Water Garden, a quiet corner with shooting fountains. After being together for a little while, Will and Allie took a trip to Longwood Gardens - Will's first time in years, and Allie's first time ever. Allie fell in love immediately. Every so often, Will and Allie would take a trip out of the city to spend the day there, wandering the gardens and fields. On Christmas this past year, Will and Allie visited again to see the holiday displays. They roamed the gardens, eventually stopping at the Italian Water Garden. Will dropped to one knee, presented Allie her grandmother's ring, and asked her to marry him. She said yes.