Lindsey and AJ

Marriage Proposal Ideas in Downtown, Chicago

How We Met

AJ and I met freshman year of high school. We began our relationship Junior year of high school. Little did I know AJ would become the first and last boyfriend I’d ever have.

Lindsey and AJ's Engagement in Downtown, Chicago

How He Asked

The proposal came as somewhat of a surprise to me. As surprised as a girl who has been dating someone for 11 years could be. The last 2 years of our relationship I would send AJ pictures of engagement rings. Little did I know the last 3 months leading up to our engagement he had been secretly meeting with our family jeweler.

AJ and I both live in the greatest city in the world, Chicago! At the time of our engagement we both lived separately.

It was St. Patrick’s Day weekend, AJ and I had just watched the river dyed green with his family. After that AJ’s sister, Amy and I went to a couple small shops while his parents “headed back to the suburbs” and AJ “went home.” When Amy and I finished at the shops I walked home. When I opened my front door there was a small table sitting in the entry way. Sitting on the table were roses and a remote control that said “play me.”

I walked into my family room and the TV was on. I pressed play on the remote control and a slide show started. First there were pictures of AJ and I in high school, next college, then present day. Every few slides marked a milestone in our relationship “this is where we met,” this is where our love grew,” “this is where I asked your dad for his blessing,” followed by the last slide, a picture of my balcony that read “and this is where I ask you to marry me.” I walked outside, dressed in full St. Patty’s day gear on and AJ was standing there. The most beautiful man inside out I have ever seen holding the most beautiful ring I could ever imagine.

Lindsey's Proposal in Downtown, Chicago

I was even more shocked to walk back into our condo only to see my parents had flown in from Seattle and AJ’s family did not actually go back home, but hid out at my sister’s condo to surprise me. After that my sisters and AJ planned a big engagement party for that same day. It was filled with all of our friends and catered by my favorite restaurants. it was the perfect proposal.

Now I get to spend forever with my high school sweetheart.

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