Tyler and Skylar met in August of 2018, after she slid into his Twitter DMs - sending only her Snapchat, they began talking every day.

After about a week of Snapchatting, Tyler came over for dinner and to help Skylar build a dresser for her apartment. Skylar being herself, had already built the frame before he got there but told Tyler she needed help with the drawers. Little did Tyler know that she had already build 2 out of the 6 drawers too, and then proceeded to take them apart before he got there, so he could help her. After their initial date, Tyler got tickets to Thomas Rhett at the fair for Skylar's birthday gift, since then, they go see a concert (or two) at the Iowa State Fair for Skylar's birthday.

In September that year, Skylar proceeded to explain to Tyler that he did in fact actually need to ask her to be his girlfriend, as he had just assumed that since he took her to a concert, that would be their anniversary date. He finally asked her to be his girlfriend on the 20th of September.

Each year that passed between Skylar and Tyler brought new memories ,from graduating college, rescuing a dog, living together, and after 5 years finally get to marry one another.