James & Rachel
JamesSimpson
&RachelO’Connell
April132025
East Haddam, CT
Our Story
How We Met
It is said that a soulmate is always connected to you by an invisible string. This string weaves through our lives, guiding us towards one another, even when we don’t realize it. Our paths crossed many times over the years, but it wasn’t until the universe decided the time was right that we truly came together.
This is the essence of the Invisible String Theory, and it perfectly encapsulates our story.
Jimmy and Rachel’s paths have intertwined in the most unexpected ways. Jimmy attended Xavier High School while Rachel was a student at its sister school, Mercy High School, just down the street. It’s likely that they were at the same school events without ever meeting. Rachel was even at Jimmy’s high school graduation, as he was in the same class as her brother. Over the years, they discovered that they had attended the same concerts and shared many of the same spaces without ever running into each other.
The invisible string was at work, pulling their lives closer together, but it wasn’t until July 18, 2022, that their paths truly aligned. On that day, Rachel began her new job at the Old Saybrook Police Department, where Jimmy was already working. As they worked together, their connection grew stronger.
Fast forward to January 13, 2023. Rachel was working the day shift while Jimmy, who had the day off, took a road job just to see her and ask her out (how cute!). Although his road job was canceled and he wasn't there in person, he still made the effort and asked Rachel out on a date that evening. Their first date took place at Taphouse 180, where they talked and laughed for four straight hours. After the date, Jimmy walked Rachel to her car and seal the deal with a kiss!
And so began their journey together, with the invisible string tying them closer than ever.
The Proposal
Then came February 29, 2024—Leap Day. Jimmy decided it was the perfect moment to ask Rachel the question she had been dying to hear. Jimmy planned a walk with their pups at the Middletown Reservoir, and to make the moment even more special, he had his brother, Connor, join them to capture the moment as the photographer. Jimmy and Connor had been planning this for a bit and Connor had previously mentioned wanting to take their pups on hikes with his friends and Jimmy mentioned having him hike with Rachel and him first to see how the dogs act.
As they enjoyed their walk, Jimmy stopped at a charming lookout to take some cute family pictures with the dogs. It was there, surrounded by the beauty of nature and their beloved pets, that Jimmy got down on one knee and asked Rachel to marry him. And, of course, she said yes!