McKenna grew up in Mundelein, IL and went to Mundelein High School, while Tyler went to the rival high school in Mundelein, Carmel Catholic. For years, McKenna and Tyler ended up at the same bars, had many mutual friends, and even had family members that knew each other, but they never met, until their first date. Tyler complimented McKenna on her smile on a dating website Hinge, and soon they were at Tuco and Blondie, a popular Mexican restaurant in Lakeview, Chicago for their first date. After stuffing their faces with fajitas, Tyler asked McKenna to go get ice cream, even though it was a freezing Chicago February night, and she was beyond full, McKenna agreed because neither of them wanted to say goodnight. Tyler walked McKenna home, even though it was the wrong direction, and asked her for a second date before she even got in her front door. The rest is history.

McKenna and Tyler went up to her family's lakehouse in Whitewater, WI for a weekend in late September 2021. In order to get McKenna to look presentable, instead of rocking her usual lake girl bum look, Tyler told her they were going to a nice steakhouse dinner to celebrate his upcoming birthday. Tyler suggested a nice sunset cruise on the lake before the "dinner reservation." Once the pontoon docked, Tyler asked McKenna to watch the sunset on the pier, knowing sunsets, especially in Whitewater, were one of McKenna's favorite things. While sitting on the pier, Tyler gave McKenna a gift. It was a cartoon book, walking through the story of McKenna and Tyler's love. Once McKenna finished reading the book, Tyler stood her up right at the edge of the pier. With the faint sound of "Marry Me" by Train playing from the house speakers, Tyler told McKenna how much he loved her and asked her to marry him. With tears streaming down her cheeks, McKenna accepted! A commotion erupted from the bushes as McKenna AND Tyler's families jumped out from where they were hiding to cheer on their two families becoming ONE! Needless to say, McKenna did not get the steak she was looking forward to, but did get herself a fiance!