Lindsay and Michael

Wedding Proposal Ideas in Millennial Park, Downtown Chicago

How We Met

As is common with a lot of millennials, Mike and I met on OK Cupid. I was sitting in LAX Airport, hungover and more than ready to get back home to Chicago, and my phone buzzes with a message with Mike. He was also on vacation at the time, so with nothing else to do we struck up conversation. We messaged for almost two weeks before we agreed to meet, which was normal considering he works two jobs, and I both work and go to school. Finding a mutually agreeable time is always half the battle (and continues to be half the battle even now). We agreed to a Wednesday night, but after more conversation Mike decided he wanted to see me sooner, and proposed a date night for the day he got home from vacation, which was a Sunday.

Mike was very persistent about taking me to dinner. This was against my motto. I usually went out for coffee or drinks; something I could easily get away from. But he kept insisting on dinner. I realized that one of my favorite restaurants was halfway between my house and his, so I may have taken advantage of his willingness to go for a meal instead of coffee ;) Before the first date was over, Mike asked me if I was still free for Wednesday (our originally scheduled date), and our second date was set before the first was over.

The rest is history.

how they asked

Engagement became a popular conversation between us, but I have a very particular taste. I was anxious for him to pick out a ring, and I am not sure he wanted that pressure. So we designed it together. Mike asked my mom for her stone from her engagement ring from my dad, and we went to a reputable family-owned jewelry store near our home to design a ring. Once it was designed and I approved each process, I was unknowingly left out of the process.

I would constantly tell Mike I was going to call the store to ask for an update. To which he would respond that it is the holiday season and things are probably backed up, there is no rush. This made sense, but he would have to talk me down daily. It then got to a point where I was sure he had picked up the ring, and I would ask, “are you going to propose to me today?” and he would look at me like I was crazy.

On the day that Mike proposed he suggested that we go downtown that evening, see the Christmas Tree, and go to the Chriskindle Market. This has been a tradition of mine since I was a child, and something the two of us have done every year since we started dating. I jokingly said, “are you going to propose to me tonight, because if you are that will decide whether I put on make-up.” Cunningly, he remembered I also had a baby shower to go to in the afternoon, so he said, “well aren’t you putting make up on for the shower anyways?” He was right, so I sulked and walked away.

When it was time for us to head downtown I scanned his pockets looking for a bulge. Nothing. I was sad, but also excited to go.The weather was perfect, so it was crowded, and the spirit of the season was definitely buzzing around us. Once we finished at the market, we headed to Millennial Park to see the tree and take our annual photo from the spot we always take our photo from. It is tradition for me to find a stranger to take our photo so that we aren’t stuck with selfies. As I was finding someone to ask, Mike takes the ring out of his pocket (the ring, NOT the box, hence why I couldn’t find a bulge), and hides it until we pose for the photo.

The photographer and his girlfriend noticed the ring before I did. It was a mixture of confusion and excitement wondering why everyone around us was staring at us taking a picture, and then realizing it was because he pulled out the ring. Once I said yes, and the “photographer” (Stranger) took a bunch of (terrible) photos (because he got really excited and stopped paying attention to the camera), strangers came up and asked to see the ring, congratulate us, and share in our excitement.

Where to Propose in Millennial Park, Downtown Chicago

Mike found a way to surprise me when I thought I couldn’t be surprised.

Special Thanks

BJ Aguado Photography
Bella Cosa Jewelers
Ring Design