Cara and Matt

How We Met

Matt and I met a few years ago through a mutual friend and the rest is history. We both knew a bunch of the same people but had never met in person. We went on our first date in fall of 2014 and have been pretty much inseparable ever since. We moved in together a little over a year ago and plan to wed September of next year at a Country Club where his parents have been members for years!

How He Asked

A couple weeks before the engagement, Matt had mentioned that he made plans to go over to his brother’s brand new rooftop, which has amazing 360 views of the city to hang out and have some drinks then go to dinner. We had been together the entire day, getting brunch and going for a walk down by the lakefront, where I never encountered him to be nervous or acting “weird.” We got back from our walk, got ready and headed over to his brothers. When we got there, I asked him if we were going to go to the apartment first to meet them and he responded “no they are already up on the roof, we are meeting them there.” As we got to the roof and opened the door, I noticed someone peeking out from behind a ledge- he had hired a professional photographer to capture the whole thing! There was champagne, candles and even rose petals set up all over the roof deck, and no one else was up there besides us (it was also the most perfect summer day- clear blue skies.) I immediately figured out what was happening and turned around and there he was on one knee asking me to marry him! I was so happy and overwhelmed with joy that I think I blacked out at that moment.

Marriage Proposal Ideas in Chicago, IL

Engagement Proposal Ideas in Chicago, IL

Afterwards, little did I know, my parents and his were waiting downstairs in his brother’s apartment to come celebrate with us! They all came up; we drank lots of champagne to celebrate and then headed out to one of our favorite steakhouses in the city for dinner. It was by far the best day of both of our lives!

Special Thanks

Arielle Gallione
Photographer