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A Breathtaking Michigan Avenue Proposal

This proposal on Michigan Avenue was one of the most romantic we have seen to date.

This wasn’t just any proposal, it was more of an event! An event that started early that morning, and continued late through the night. We are so excited for the happy couple and were thrilled to be a part in putting this special moment together.


VRAI Photography

When I say this proposal was more of an event, I’m not joking around. Matthew went above and beyond in making this two-year anniversary one to remember. Kristen had no idea what was going to happen that evening, even despite everything Matt had planned throughout the day.

It all started with a helicopter ride. But not just any helicopter ride, a helicopter ride over the city and Wrigley Field!

The two met just a few years prior at Wrigley while they were enjoying a Jason Aldean concert. Coincidentally, they were both trying to get as close to the front as possible (because who wouldn’t?). Out of their assigned seats, the two kept inching closer and closer together until they were sitting right next to each other. A little conversation and a few laughs later, that happy accident turned into love. Matt wanted to be sure to capture that moment they met, so when the helicopter flew over Wrigley, the pilot made a sweet announcement, “Happy Two Year Anniversary”. But even then, Kristen didn’t expect a thing.

As the helicopter landed, the two headed back to their beautiful home in the city to get ready for a fancy dinner for two! Matthew slid the ring in his suit pocket while Kristen touched up her lipstick and slipped on her heels, and they headed down to the cab which would bring them to Spiaggia’s. A 14 course meal and beautiful bottle of wine awaited them. Yet Kristen still had no idea. Kristen had told us later on that he wasn’t acting the least bit nervous, which is incredibly impressive considering just a few blocks away, Visions was setting up their proposal scene where he would get down on his knee and ask for Kristen’s hand in marriage.

After what had already been such a special day for the two of them, Kristen had no idea what was about to happen. The couple walked hand in hand down Michigan Avenue where they would cross paths with an acoustic guitarist playing their song, Mirrors by Justin Timberlake. We were almost brought to tears as the handsome couple danced in the center of all the hustle and bustle of Michigan Avenue.

And then the moment came. Matthew dropped to his knee and popped the question. Kristin could hardly contain herself because she genuinely had no idea it was coming! The couple basked in happiness and had their first photo shoot as an engaged couple with Vrai Photography.

Think it ends there? Wrong! Matthew had one more surprise up his sleeve. The couple headed back home where Kristin would find a surprise engagement party on the rooftop overlooking the city. Only their closest friends and family attended, and it was the perfect end to the day.

We have never seen such a proposal. One that truly lasted all day, yet Kristen was still completely swept off her feet in the center of Michigan Avenue. Kristen and Matthew had an anniversary that will never be forgotten and we are overjoyed for the happy couple.

Be sure to keep your eye out for Kristen’s Q&A in our next version of Diary of a Busy Bride. She’s giving us all the inside deets on how she felt during the proposal and her future wedding plans!


MKVP_023 MichiganAve_Proposal4MKVP_032MKVP_036MKVP_046MKVP_049MichiganAve_Proposal5MichiganAve_Proposal6MKVP_064MichiganAve_Proposal7Check back tomorrow for a follow up interview with the happy couple!

About Jenée Strickland

Visions Event Studio specializes in luxury events, including proposals and couture weddings. Jenée Strickland, owner, and lead visionnaire, has been an integral part of hundreds of weddings and proposals. Her job is a privilege; her work is a passion.

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