It wasn't anything close to love at first sight for Alden and Vanessa, at least not from her perspective. It wasn't love even at second, third, or fourth sight, and she would later recount with a wry smile that she thought he was full of himself the entire first year they knew each other. Alden had attended medical school with Vanessa's brother, Franklin, and was a frequent fixture at their family's dinner table through their internships and residencies. For his part, Alden's first impression of his best friend's sister was that she was outspoken and opinionated, and nearly impossible to impress no matter how hard he tried. But fate worked its magic somehow, and five years almost to the day after they first met, Alden and Vanessa were exchanging vows in front of a large congregation to spend the rest of their lives together.

The Stones had their first and only child relatively late in life. They always knew they wanted to have children, but figuring out a good time to do so proved to be a more difficult decision. After half-heartedly trying to have children for years and being unsuccessful at it, they eventually reconciled to the idea that perhaps it just wasn't meant to be. Alden was making a name for himself as a surgeon, and Vanessa had been made a senior partner at her law firm, so the idea of having a family was shelved. When Vanessa one day suddenly came to find herself pregnant well into her thirties, it came as a surprise to everyone. Jackson was born on a warm spring day, and from the beginning it was clear that he took after both of his parents.

A bigger surprise still came a few years later when Vanessa's brother's wife tragically passed away from cancer, and Franklin's inability to cope with the loss made it necessary for the Stones to step in and care for his two young children. Some of Jackson's earliest and fondest memories were those of growing up with his cousins. Being so young when everything happened, they were more like siblings to him, and that was further cemented when the Stones decided to officially adopt Sasha and Dylan soon after. Jackson's parents, who just a few years ago had thought they wouldn’t have any children, now had three and were determined to propel them all towards leading successful and rewarding lives as upstanding, responsible members of society.

Impulsive and reckless even as a toddler, Jackson only became more so as a teenager. Despite his parents' frequent lectures and attempts to ground him, Jackson wouldn’t learn the lesson that he wasn't in fact indestructible until the summer after his junior year, when he was involved in serious accident that totaled his new car and landed him in the hospital with a coma for four days. He spent the entire summer in physical therapy, and the damage to his knee in particular ruled out playing any sports his senior year.

Despite the odds, he managed to make it through high school in one piece. The accidentally that had come close to taking his life succeeded in putting things a little more into perspective for him, and he left Boston to attend Swarthmore College and try to make something of himself, although he didn't lose his penchant for thrill-seeking and risk-taking. There were no more near-death experiences, but life was anything but boring for Jackson. After graduating with a major in mathematics and minor and statistics, and worked for a time as an analyst at a financial consulting firm. The fast pace, high stakes, and challenge of the work was exactly what he wanted, and after a couple of years he decided to go to business school and earn an MBA. He stayed in Philadelphia for a brief time, in which he embarked on a business venture with a friend from school, until an irreconcilable difference of opinion ended the partnership. Jackson decided to return home to Boston in 2014.

Soon after returning to his hometown, Jackson found work as a financial advisor at Matfield Financial, an international wealth management corporation with an office in Boston. The next few years went by quickly, and he spent the majority of his time advancing his career, thrill-seeking, and playing cool uncle to his sister's kids. In 2018, his life was shaken up by a chance encounter with someone with whom he'd once shared a week-long tryst while on a business trip in Tokyo - who revealed that she had a baby nine months after he left. Fatherhood wasn't something he'd ever planned on, but in some ways it's changed his life for the better.