Caitlin and Matt

Engagement Proposal Ideas in Chicago, IL

How We Met

I met Matt when I was 15 years old on the first day of summer vacation 2005. We were introduced by our mutual friend, since they lived in the same neighborhood. It’s funny because at such a young age neither of us set out to find a partner in one another after meeting, but we both became quick best friends. Over the summer and new school year we started to develop feelings for each other. We would hang out all the time and I knew he would try to sneakily catch me in the hallways just to say hi. We didn’t become official until February 2006. He finally admitted feelings for me on Valentine’s Day in a drug-induced stupor from appendectomy procedure over the phone, calling from his hospital bed. We made it official a couple of weeks later, and after over 10 years of friendship and love we have created so many incredible memories together. My favorite part of our story is that because we were so young when we met, we have been able to grow up together and know each other at every age and life phase.

How He Asked

The week before our proposal I had been pestering Matt about planning a fun date for the weekend, which for once wasn’t filled with plans. When we woke up Saturday it appeared to be an average day, with our routine errands. However, Matt had been acting strange all morning. He had woken up at 8 am which is way earlier than his usual weekend 10 am wake up call (by me).Matt said he had to go into work that Saturday afternoon to work on a big game project. Then at the gym he couldn’t run on the treadmill because he was “anxious about work”. I naturally said “you’ll be fine!” and went on with the day, while Matt waited around to “go to work” at 1 pm. I was taking my usual weekend cat nap when I heard my phone buzz.

Matt was hurried on the other line and stated, “read the card next to you and then let me know when you have finished”. I noticed the card next to me and read that I was to go to Dimo’s pizza for the start of a fun day, to get ready and head out. Still half asleep but hearing the urgency in Matt’s voice, I barely put myself together and ran out the door. All week after telling Matt to plan a fun date for Saturday I thought this must be a scavenger hunt date! I was sure that when I arrived at Dimo’s I would find Matt and have a fun Saturday date ahead. When I walked into Dimo’s I found not Matt Burke but Matt Kochis, my best friend who lived in New York.

Proposal Ideas Chicago, IL

Immediately, I started crying. It was such a surprise. I asked Matt, “what are you doing here?” He replied, “New York has great pizza, but nothing beats Dimo’s.” He gave me the next clue and off we went on a whirlwind adventure. Next stop was Houndstooth Saloon, another old stomping ground. Saturday being a college game day it was really crowded. Matt guided me to the patio outside and none other than Ben Kwedar and Marty Cawley were waiting at the table. At this point, with Matt Burke nowhere to be found, I was starting to think this was a much more special moment than originally anticipated.

Where to Propose in Chicago, IL

I decided to enjoy the company at the moment rather than think about what lay ahead. We enjoyed a pitcher and moved onto the next clue…Trader Todd’s. Who awaited were none other than my friends Alyssa and Jilly ready to take a shotski to celebrate the adventure. My next clue lead me to the ultimate stomping ground, DePaul University Quad.

It was a long trek to DePaul Quad from Trader Todd’s but with five friends in tow to enjoy the gorgeous October day, it couldn’t have been more pleasant. I lead the way up Fullerton Avenue to Seminary to the main entrance to the Quad. Immediately, passing the fenced area I saw a Delta Gamma welcome wagon. Sisters began chanting and screaming and I turned to my friends and said “I have to run. I have to run home!” and booked it.

Never in my wildest dreams did I expect to get the chance to run home to my sorority sisters after so long. Tears, hugs, and laughs were shared as well as a special ritual Oath, and I was given yet another clue and sent on my way, this time alone without friends. It appeared to be the end of the journey and knew her next stop was Kelly’s Pub, a three generation Boshardy stomping ground. I was confident that my brother Leo would be waiting for me. Crying all the way from DePaul to Kelly’s overwhelmed with love and gratitude, I walked into Kelly’s to find my mother, father and brother.

We kissed, hugged and took a quick pic and I left for the final stop on my hunt. My college stoop on Sheffield Avenue. Finally, there was Matt Burke. He waited on the stoop we shared so many fond memories on what we believe to be the epitome of city living.

Matt asked, “did you have fun?” I was so overwhelmed I just nodded and said, “it was so much fun.” Matt said “I wanted you to know how much you are loved and how much family you have. I want to be a part of that family and make a family with you.” He proposed then and there and with one final ace in the hole, surprised me with an engagement party at Kincade’s with closest family and friends. So far, we we consider it to be the best day ever.