The story begins with Jake and Kim meeting through a mutual friend, Elliot. Over text, Jake asks Kim if she is a cat or dog person. After responding she is a dog person, Jake replies he is a cat person but opposites attract. This line must've worked because a few days later, Jake and Kim have their first date at a pizza place in Center City Philadelphia. They share stories over pizza and wine and discover common interests in sports and hobbies, like soccer and reading Harry Potter in different languages. Elliot happened to be at a bar next door, and Jake and Kim join him and continue the fun night. The pair bond while drinking cocktails and listening to jazz music. At the end of the night, Jake walks Kim back to her apartment building and kisses her goodnight.

On a Friday evening, Jakes takes Kim on a date to Zavino, the resturant where they had their first date. Over pizza and wine, they reminisce about the past two years together. Leaving the restaurant, it starts to drizzle. Jake leads Kim towards Rittenhouse Square. The Square is lit for Christmas with white lights among the branches and a Christmas tree in the center. In front of the tree, Jake takes Kim's hands in his, tells her he loves her and wants to spend the rest of his life with her. He goes down on one knee and presents a ring. She says, "yes of course!" Jake's brother emerges from the park, having photographed the magical moment. A would-be random Friday night becomes an unforgettable evening.