It all started like any unexpected summer romance. Sam and Kaitlin met at a mutual friend's graduation party. Kaitlin's brother, Jon, introduced the couple since he and Sam were old friends. The three of them, along with a few others, all went and shot-gunned a beer together. Shortly after, Sam had to leave and that was that. Two weeks later, Sam showed up to Kaitlin's cousin's graduation party and approached Kaitlin as she was drinking a corona. He went up to her and asked, "Are you going to shotgun that?" Kaitlin laughed and asked for Sam's name again and promised she would remember this time because he had the same name as her best friend. As the night went on, the couple engaged in conversation about how Sam currently lived in Boston for school. Kaitlin figured nothing would come of it, but she proceeded to take his phone number anyhow. The two continued to hang out most of the summer before Sam went back to school in Boston. As summer came to an end, they took a shot at being in a long distance relationship and we all know how that worked out ;)
During the midst of a pandemic, Sam and Kaitlin decided to book a spontaneous trip to NYC since Kaitlin's brother, Jon, would be covid-testing in the area. (Also because flights and hotels were too cheap to pass up.) Sam didn't know he was going to propose on this trip until the flights were booked four days before they left. Luckily he already had the ring and was waiting for the right opportunity. They arrived in NY on Saturday and Sam quickly tried to figure out his proposal plan. Saturday came and went. He wanted to wait for the sunset on Sunday, but that passed too. Finally came Monday. They woke up Monday morning and went to breakfast, then ice skated in Bryant Park. Afterwards, they started walking up to Central Park. Once they approached the park, the three were greeted by a man who was trying to pitch them on taking a carriage ride all through the park. Jon was sold on this plan even though he knew Sam needed to propose on foot. Sam proceeded to walk away and tried to find his proposal spot. They came to a spot called Umpire Rock and Sam asked if Kaitlin wanted to take a photo. Jon handed Sam the ring box behind Kaitlin's back and went to take their picture. Sam started looking and smiling at Kaitlin and that's when he proceeded to get down on one knee and propose. He gave her a rock on the rock.