Katherine and Paul's Romantic Chicago Bridge Proposal

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How We Met

Paul and I met through our roommates in Chicago. I was looking for a new apartment and found a few girls on Craigslist who needed a fourth roommate to go in on the Wrigleyville condo they’d found for rent. I was heading home from Manistee, MI (where my family has a summer home and also where we’re getting married this September) on Labor Day in 2012 and made plans to join the girls for dinner at the Wheel House (now Butchers Tap) in Southport corridor so we could all meet. I brought my boxer Ivy so they could meet her too. Ashton, Lauren, Sarah and I sat on the patio, chatted, got to know one another and decided to pull the trigger on the condo for rent on Cornelia Avenue. Sarah had spent the day with her boyfriend and his friend and tennis doubles partner Paul, so they tagged along and had a drink at the bar. As we wrapping up, they came out and introduced themselves. That’s the first time I met my fiance Paul.

Paul and I met through our roommates in Chicago. I had tickets to see the Lumineers at The Riv. I was going with my friend Renee and my brother and had talked about meeting up with my roommate Sarah and her boyfriend who also had tickets to the show. My roommate Sarah had asked for an extra ticket for another friend. That friend was Paul. I caught up with my roommate at the show and Paul eventually made his way through the crowd.

Paul and I went for a night cap after the concert together. Paul asked if he could buy me a drink. We talked, laughed.

As we were leaving, he offered to give us a ride home. I thanked him, but said we’d just hop in a cab. Paul said he had a nice time and it’d be great to get together again. I agreed. Then asked if he was going to ask for my number. He took it and called the next day.

Image 2 of Katherine and Paul

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how they asked – by the bride

Paul and I had no plans the Saturday before St. Patrick’s Day and we had the best day together. We went downtown the two of us, checked out the parade, stopped at a few Irish pubs and just enjoyed Chicago. I told him that day we should do this more often — and I walked right into his plan.

That week, Paul told me he planned a special “date night” for us on Friday. He told me to plan on going straight from work to the reservations he’d made at Bavette’s.

I called him over lunch on Friday to say hi. I didn’t get him, but he called me back and told me he wanted to stop and meet our realtor for a showing on the way to dinner.

He picked me up from the office a little after 5pm and we stopped by to check out 345 N. Canal. We did the walk through, talked about the potential layout and asked all the standard questions. What I didn’t know at the time, was the showing was all a ploy to get me to walk across the Kinzie Street bridge.

Paul and I started walking towards our dinner destination as we had left from a viewing of a condo as we are condo shopping for a place together. As we rounded the corner onto The Kinzie Street Bridge, he started slowing down (and he always walks fast). We stopped in the middle and Paul said how much he liked that view of the city. I agreed. He told me he loved me so much. I said, “I love you too, babe.” Then he got down on one knee and asked me three questions: “Will you hang with me for the next 50-60 years? Will you marry me? You promise?”

I said yes!

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Before Paul could put the ring on my finger, Paul’s family started walking across the bridge. My mom and dad were steps behind them. So were Paul’s mom, sister Laura and brother-in-law Seth, and my godfather, Uncle Tommy. My brother Brendan and his girlfriend Michelle were there too. They’d flown in from Toronto but were delayed, so had literally hopped out of their cab and dropped their bags just as Paul got down on his knee to propose. Paul’s brother in law’s son Matt and his girlfriend had our dog Ivy in hand with flowers around her neck.
I was overwhelmed and so in love.

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Our guitar teacher Jason McInnes was playing a couple of our favorite songs that Paul had asked him to learn. We popped champagne and cheersed to our future together. My dad made a toast that brought us to tears. He quoted Crosby Stills Nash and Young saying “a man’s a man who looks a man right between the eyes”. He went on to say how happy he and my mom were to see me so happy and that I found a man who values family, tradition and large romantic gestures.

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We celebrated on the Kinzie bridge, unbothered by the passersby getting off of work on a Friday afternoon. We had homemade “Marry me?” signs (compliments of my dad and Uncle Tommy) and sparklers. We danced, hugged and talked about all the thought and planning that Paul put into it.

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I learned that Paul had taken the train to Ann Arbor, MI a month prior (while I was in Toronto) to ask my parents in person for permission to marry me. He also coordinated with my cousin Kimmy to shift my goddaughter Harper’s 2nd birthday party to the following weekend, because he knew if her party were the weekend of March 18th that there wasn’t a chance I’d be in Chicago.

We were surrounded by all of our favorite people and we were ENGAGED! Even better, it wasn’t over. Paul had set us up to spend the weekend together and made reservations for everyone to stay at the Chicago Athletic Association Hotel.

I couldn’t imagine a more perfect proposal or man to spend the rest of my life with. We can’t thank our photographer Renae Johannes enough for capturing gorgeous pictures that we’ll always have to remember the moment.

how they asked – by the groom

I had been thinking about proposing to my beautiful fiancé Katherine for a couple of months and had started to look at rings in December/January. Over the holidays when we were visiting Katherine’s parents in Northville, MI a good time never really presented itself to sit down with them and and ask for their blessing. So when Katherine planned a weekend trip out of town in late February to visit her brother (who lives in Toronto), I used the opportunity to reach out to her parents and ask them if we could meet for a “secret” dinner on the Saturday night of February 20th, 2016.

I took the 4 hour train ride from Chicago to Ann Arbor, MI and sat down with Katherine’s parents to ask for their blessing. Both of them could not have been more supportive or excited for us. They really appreciated me making the trip and for meeting with them to ask face to face. After a long night of great conversation, we started to set plans in motion for the surprise proposal. I coordinated the proposal so that my family and Katherine’s could come and surprise her.

I don’t think any of us knew how difficult it would be keeping the secret for that long. Katherine and her parents are very close and talk to each other daily. Luckily none of us slipped up and the night of the proposal I was pretty confident Katherine had no idea what was going on.

I knew I wanted to propose to Katherine in Chicago in an outdoor setting. As residents of Chicago for almost 10 years I wanted a place that was a little more unique than some of the standard tourist spots. I decided that the Kinzie Street bridge with its great views of the Chicago river and the loop skyscrapers would be a good choice. Also, its proximity to Katherine’s office in the loop would help play into my idea for a Friday “date night” dinner to meet up with some friends.

On the day of the proposal I woke up playing fun songs and couldn’t wait to meet up with all of our family to get the day in motion. I’m sure when Katherine left for work in the morning she had probably noticed I was in an extra good mood. As soon as she left I had to jump into action and pack her bags for the long weekend. I reserved a suite for us at the new Chicago Athletic Hotel along with rooms for all of our family. My mom arrived to help complete the packing and we headed downtown to get checked into the hotel and setup the suite with champagne, cocktails, and hors d’oeuvres for the post-proposal celebration.

As family funneled into the hotel, we all met in our suite and headed towards the bride around 3pm. We went over plans for where the family should be setup on the east side of the bridge and cues on when they should start walking towards us.

Katherine and I have been practicing guitar for about a year at the Old Town School of Folk music so I invited our guitar instructor to come and play a few songs as well.

At 4:45pm I left to go pickup Katherine for our “date.” In K’s usual style I anxiously waited at her office for about 10 min before she came down. We small talked on the drive over to the bridge, and at this point I’m getting very nervous. I had scheduled a “fake” real estate showing with a broker friend of ours to view a condo, This was the only way I could figure out how or why we would be walking over the bridge in which I had planned to get down on one knee.

As we left the showing my palms were sweating pretty bad. I hadn’t planned on how large the engagement ring box was, and was doing all I could to conceal it in my right hand/pocket while being sure to hold K’s hand with my left.

We finally made it to the bridge and my notoriously fast walk slowed to a creep as the nerves built up. Everything gets a little fuzzy after that but from what I remember I commented on the beautiful view and asked Katherine to look out over the water for a second. Then I pulled her towards me, got down on one knee and asked her what she if she wouldn’t mind spending the next 50-60 years with me. After she said yes, I reacted with an excited “you promise!!??”

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All of our close family, our guitar instructor and our 6 year old boxer named Ivy flooded the bridge with perfect timing. We shared some great hugs, some tears and it was all capped off by a beautiful toast from Katherine’s dad Gary, which I will never forget. We had an amazing weekend with everyone downtown and I couldn’t be happier to soon be marrying my bride.

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Special Thanks

City Savvy Imaging
 | Photographer
Jason McInnes
 | Guitar Instructor/Performer