We first matched on Hinge during COVID, when dating meant getting creative. Our first date was a picnic in Lincoln Park. Grant showed up on a bicycle, which Penelope thought was odd, but he made up for it by walking her home completely out of his way. That effort led to a second date: drinks at one of the first restaurants to reopen, followed by rooftop views of the Chicago skyline. From there, summer became street festivals, lakefront walks, and paint-and-wine nights at home. Less than a year in, Penelope got a job offer in California. The details are fuzzy: Grant remembers her asking him to move, and Penelope remembers him saying he would come if she went. Either way, it was a big step. Grant was nervous to tell his family, but to his surprise, they were completely supportive. Soon after, the two of them were off to start a new chapter in San Francisco. Four years later, Wharton brought them to Philadelphia. By then, they had shared travels, countless home-cooked meals, and plenty of adventures together. Each chapter has only proven that when it is the right person, every leap feels worth it. During a trip back to Chicago for an MBA admit weekend, Grant proposed in Lincoln Park. Not at the exact picnic spot, but in the place where they so often took long walks and watched the sunset. It was the perfect full-circle moment in the city where their story began.