Garrett and Courtney met at brunch - can't get more basic Chicago than that (RIP Zella) - but the story actually goes back much further. It was spring break 2013; both Garrett and Courtney were stuck at home surviving the bitter cold while their friends ventured down towards the always classy Panama City Beach. It was on this fateful journey that their separate friend groups would eventually cross paths and unknowingly lay the groundwork for their future romance. It would still be a few years, and a number of missed encounters, until the day that Joe (the best man) would convince Garrett to begrudgingly join him for a typical and unassuming Saturday Brunch. It was there, at the infamous Zella, where Courtney and Garrett met. They ended up hitting it off - after he had cookies and ice cream delivered - and the rest is history. They have talked every day since.

With a looming two week trip to Europe, Garrett had to make the tough decision - could he pull off a successful overseas proposal? After contacting photographers in Italy via broken English emails, Googling romantic cliff side locations in Positano, and considering the possibility of losing the ring on the way, Garrett opted for a less intimidating state-side approach. It was a clear summer day in Chicago and the city skyline was standing tall in the background of their apartment rooftop. Andy was in place hiding out with his iPhone ready. There was a two hour window to execute the plan before an Uber would scoop them up for an overnight flight to Germany. Garrett, heart racing and palms sweating, picked Courtney up from work and headed back home where everything was in place. That's when Courtney hit Garrett with "I really need to stop at Macy's to return this $25 shirt before we leave". ARE YOU KIDDING ME. She wouldn't let it go. He pushed, he pleaded, he made up excuses, but in the end, she made him stop at Macy's - for a $25 shirt. Two hours turned into one and time started to dwindle. He was finally able to get her to the roof where he got down on one knee and popped the question. And yes, they made their flight. Next stop....Oktoberfest.