Despite liking his best friends' sister for almost an entire year, Ryan finally asked Leeann to be his girlfriend on the 22nd of November - almost 10 years ago now. He waited until the 22nd of that month because he remembered that she once told him 22 was her favorite number.

Ryan graduated High School and left Wayland for college!

Leeann graduated High School and left Wayland to study Interior Design at RIT!

COVID-19 forced Leeann out of her dorm and back into her parents' house in March of her freshman year. Later that summer, Ryan and Leeann moved into their apartment in Henrietta to be closer to RIT. This picture was their first day in their new apartment, eating lunch on the floor with a storage tote as their table because they didn't have any furniture!

Olivia Ryan Flagg entered the world, making Ryan and Leeann Aunt and Uncle!

Ryan bought a house! After much hunting, they settled in LeRoy, NY, where Ryan's brother, Justin, had stayed. Four years later, Leeann's brother Greyson and his wife Sarah joined them all in LeRoy! The three couples and two sibling pairings have loved living close to each other in the same town!

The day before Leeann's 21st birthday, Ryan brought their first puppy, Luna, home! She became their whole world and the biggest joy of their lives, yet! 🐾🤎

Until they brought Billie home! Billie was originally supposed to be Ryan's parents' dog, but they needed a puppy sitter for their post-holiday cruise, and Ryan and Leeann needed to train their puppy to be okay with having other dogs in her house. So, it was a win-win situation for Ryan and Leeann to care for Billie during that time. 18 days later, Lori and Charlie weren't so sure about having a big dog in their house again, and Leeann couldn't bring herself to give Billie back after Luna had bonded with her. So, Ryan and Leeann accepted the challenge of having puppies under the age of 2 as Leeann finished her last semester of college. It was difficult, but oh, so worth it. Best. Decision. Ever. 🐾💛

Leeann graduated with her Bachelor of Fine Arts Degree from Rochester Institute of Technology!!!

Ryan asked Leeann to marry him!!! It was a total surprise with a very solid cover story and impeccable planning! Everything was perfect!

We can't WAIT to see you all at the wedding!