Jackson and Lindsay met on OkCupid in March 2017. Jackson and Lindsay talked for nearly a week before even knowing each other's name, and only knew each other by MC_TroubleTickle and linlad - back then, OkCupid used usernames instead of real names! Jackson was a student at Columbia College and Lindsay a student at Loyola University Chicago. March 15th, 2017 was the first of many dates and time spent together. Jackson and Lindsay met for the first time at Cheesie's on Belmont in Lakeview, where they ate grilled cheese and drew anime characters on the chalkboard table. Their second date was at Nori Sushi on Devon Ave in Rogers Park, where they witnessed a bird murder. Seeing Your Name (Kimi No Na Wa) at the Century 12 Evanston was their third date... it just keeps going! The first summer that Jackson and Lindsay were together was "long-distance" - Jackson went back to his grandma's house in Missouri, and Lindsay back to her home in the suburbs of Chicago. Jackson wanted to prove his seriousness about Lindsay, and he traveled via Amtrak and Greyhound bus in order to visit Lindsay! The first few years of Jackson and Lindsay's relationship were marked by the carefree, fun times of college, where they traveled all over the city and saw countless movies at the AMC River East 21. Following college, graduating into the 2020 COVID pandemic, Jackson and Lindsay stayed in Chicago, moving in together in June 2020 to an apartment in Lakeview. Shortly thereafter, fur-baby Maru moved in, too. After a year of living in Lakeview, Jackson and Lindsay moved to a different apartment in Uptown to be closer to the lake and have more space. Maru loved the large green space right down the street from the apartment (and Lindsay has the scar to prove it!). They lived there for another two years before moving to suburbia in order to become homeowners, buying Lindsay's childhood home from her parents. Nearly nine and a half years later, Jackson and Lindsay are ready to make it legally official - after all, they're basically already married!

Jackson began planning a proposal in early 2024. After going to multiple jewelry stores, Lindsay had not found any perfect ring. So Jackson decided to custom design Lindsay's engagement ring, cherry picking design aspects that Lindsay had liked from rings they had seen. Once the ring had been made and delivered, Jackson began planning the proposal. Jackson and Lindsay had an upcoming trip to Las Vegas with an open day on their itinerary. He booked a rental car and planned to take Lindsay to see a nearby national reserve. Lindsay was extremely suspicious. On April 17th, 2024, Jackson took Lindsay on the Red Rock Canyon National Conservation Area scenic drive, stopping to check out the various trails along the way. On the SMYC Trail, Jackson proposed. It was a tender moment, filled with joy and tears and excitement. Immediately after as they headed back to the car, Lindsay slipped down the trail, earning a big bruise. To celebrate their engagement, Jackson and Lindsay went to Bavette's Bar & Boeuf for a nice dinner.

Maru was Jackson and Lindsay's first baby. She came home as a little black puppy whose ears stood up one day and never came back down. Maru was an extremely sweet girl, and she was much beloved. She has since passed away from cancer; she is gone but will never be forgotten. Two years after Maru came home, Shrimp joined the family. At the shelter, he walked up to Jackson and Lindsay and flopped over, at that time, known as Lukas. He came home that day, and he continues to stink up the house. While bold at the shelter, he's actually a very shy and skittish guy who takes time to warm up to new friends. About two years after Shrimp, the vet's office had a litter of kittens looking for their forever homes. The litter had two rambunctious boys and a feisty, sweet girl. That kitty girl came home and became known as Ebi. She is sweet and sassy, and she sometimes lets out either a raspy or tiny, little meow just to let you know she has something to say. A few months after Maru's passing, Jackson and Lindsay wanted to bring home another dog. After researching, they settled on a black lab puppy and found Moby through a breeder. Moby was born alongside seven brothers! He came home and has made himself at home in their hearts. He is extremely sweet and silly, and he does not know the concept of personal space.