In June of 2022, Madi and her mom, Denise, interviewed Tyler over FaceTime to see if he would be a suitable roommate and to ensure that Madi's room would have multiple fire exits. A month later, Madi moved from Michigan to Colorado Springs for a year-long adventure away from Michigan. Madi, Tyler, and their roommate Zosia, were successfully reenacting "New Girl" and just like in the show Madi and Tyler ruined the sanctity of the roommate relationship, accepted the risk of a super awkward breakup, and started dating 4 months after meeting.

They explored Colorado for the next year, camping, hiking, hot-springing, and checking out new sites every chance they got. The summer of 2023 brought a tough decision, move back to Michigan or continue the Air Force journey. Ultimately, they decided to take an assignment in North Carolina and determined that no matter how big the challenge they were going to choose each other.

Tyler worked with Madi's family to plan a surprise engagement trip out in Traverse City, MI over Memorial Weekend 2024. The group tried to plan out every detail to make the engagement as perfect as possible for Madi but you know how that goes. Madi came down with strep throat, got medicine for the strep throat, and then got hives (on her face) from an allergic reaction to the medicine. Besides the bad tonsils and allergies, Madi is the strongest person out there and pushed through to participate in all the fun that weekend so she wouldn't miss out on any time with her family. She said yes and they started planning for the next chapter of their adventure.