Derek and Sarite met at the joint bachelor and bachelorette party of Sarite's friends Carlye and Justin Feeney. Sarite was a bridesmaid for Carlye, but Derek didn't even know Justin or Carlye and was invited to the party by Justin's groomsman, Chris Ferguson. When they were first introduced, they were in the Hyatt hotel in downtown St Louis. After having such a great time together at the party, they continued to see each other and Derek was Sarite's guest at Carlye and Justin's wedding. Their dating anniversary happens to be the same day as their wedding!

In May 2015, Derek and Sarite went on a road trip to Montana to visit their friend Kyle Rohan. The first day of vacation was full of driving and they made it all the way to Hill City, South Dakota. Their plans for the next day were to see Mount Rushmore and go on a hike in the Black Hills. Unfortunately, it was raining that day, but Derek and Sarite did not let a little rain change their plans. They visited Mount Rushmore first and could barely see it because of the rain and fog. They walked up a bunch of stairs to get as close as they could so they could get a better glimpse. During this time, Sarite got soaked. She was wearing a wind-breaker that she thought was a raincoat, while Derek bought an expensive umbrella that he was so proud of because he didn't get as wet as Sarite. As a result, Sarite was drenched, cranky, and no longer wanted to go hiking. She expressed her feelings to Derek and said if they didn't go hiking they could see Kyle sooner and not have to drive in the dark. Derek, however, was adamant about hiking and convinced Sarite that they should eat lunch, dry off, and see if the weather cleared up. While we ate, it stopped raining and the sun came out! Sarite was slightly disappointed, but agreed to go hiking. She had no idea Derek was so interested in hiking. As it turned out, Derek had an ulterior motive. Both Sarite and Derek ended up having a really fun hike with an even better ending. When they reached the end of the trail, Sarite started to turn around and head back, but then noticed Derek was searching for something in his backpack. Wondering what he was doing, Sarite came back over to him and he got down on one knee. He pulled out a ring and asked Sarite to marry him. She was extremely surprised and happy. She even lifted him up in a big hug!