Drew and Caroline met in Seattle while they were both in pharmacy school. Caroline claims that Drew's first conversation with her was when he accused her of taking his seat before an exam. Drew believes differently. Either way, they first started hanging out when they watched Michigan basketball together during March Madness. Drew was a huge basketball fan with no team to cheer for, and Caroline was a huge Michigan fan with no TV to watch games on. They started dating at the end of their first year of pharmacy school and haven't looked back since.

Drew and Caroline got engaged on April 5, 2017 after dating for over four years. They were on vacation in Anchorage that week visiting a couple of friends. While their friends were at work one day, they decided to go on a hike. While it was cold and snowy out that day, Caroline was confused as to why Drew insisted on hiking in snow pants and made fun of how big of a baby this California man was being about the weather. It turns out, he needed pants with zippered pockets to put the ring in! After barely making it through the snowy hike, Drew started scoping out a spot with a good view, and set up his phone and gopro to take videos. It was a beautiful proposal surrounded by snow covered mountains that would mark the start of many adventures together.