They matched through the dating app, Bumble, where women have 24 hours to send the first message after they match. Well 24 hours had gone by and Kayla (ever the procrastinator) hadn't sent a message, Tyler had a good feeling about her, and wanting to give a 2nd chance, paid to extend the match. Kayla feeling impressed (and also terrible at first moves), sent the first message which was a GIF of Joey from Friends saying "how you doin'?" Tyler also being an avid Friends fan couldn't help but laugh and send a message back. After a few weeks of messaging we went on our first date where they threw darts and bowled while listening to music he put on through the Touch Tunes jukebox (started off with Kayla's favorite song "I Wanna Dance With Somebody" by Whitney Houston). They then went on a drive laughing and talking while looking at Christmas lights in the neighborhood. At the end of the date Kayla asked "when are we seeing each other next?"

On their 2 year anniversary Tyler took Kayla out to Eno Vino Downtown to celebrate. While there, he suggested they go out on the balcony to take a celebratory picture with the State Capital in the background. After a couple of pictures Tyler mentioned he had something cool sent to him earlier and thought she'd like it. Tyler handed his phone to Kayla and on the screen was Wisconsin Badger's basketball legend Frank Kaminsky (Kayla's all-time favorite Badger athlete). Tyler hit play on the video and Frank then said "Hi Kayla...", she froze because Frank Kaminsky just said her name. Frank proceeded to talk about how he appreciated Kayla being such a big Badger basketball fan of the team and hoped for a long run in March Madness. Then Frank said "Tyler has a question he'd like to ask you. Tyler my man you can take it from here." Kayla then turned to see Tyler on one knee with the ring box open with an absolutely beautiful ring inside. Tyler asked Kayla "will you marry me", and she said "YES!"