Milton and Laura

Engagement Proposal Ideas in Chicago, Illinois

how we met

It was our last first day of high school and I wasn’t expecting to meet my future hubby. All the cool gals, plus me, met in the parking lot before classes to take the cliché “Senior Pictures” which consisted of all the girls in their red senior shirts and white pants (and then there was me in my jean skirt – only because it was finger tip length & I followed all those rules). My sweet sweet friend, Caroline Moore, and I walked into our first class together. We sat down in our seats not too close to the front of the room but close enough where I was still considered to be in the front of the room. I looked across the room to make sure I had no more friends and saw this precious little guy with a giant curly afro (for real) & the sweetest smile. I leaned over to Caroline and asked who the heck this guy was, because I had never seen him before and I was so confused why I didn’t know who this person was because A) he was cute and B) he was really cute. She then simply replied “Oh, that’s Sarah Straw’s brother” which I try to shrug off like “oh of course it is, duh” even though I really wanted to know this mystery kid’s name.

Where to Propose in Chicago, Illinois

As determined as I was, I found out his name was Milton (that’s interesting), stalked him on Facebook and tried to find a reason to talk to him. I couldn’t. From the minimal information he had displayed on Facebook, there were no conversation starters, so I had to bring it back to school – like always. I think I tried to talk to him a couple of times but chickened out. Up to this point I’m pretty sure he had absolutely no idea who I was. So a few days later in government class, Milton hadn’t done his homework and was nicely embarrassed by our teacher Lisa Boulware, whom we love, and I calmly said to myself YES THIS IS MY MOMENT (I’m the goody too-shoes who does everyone’s homework). I just casually, in passing, told him that if he ever needed help with the homework he should just text me and I’d be more than willing to help (that was sweet right? I sounded like a nice girl?). Whelp, he never texted me (womp womp womp) but I wasn’t giving up. I then texted a good friend, Garrett Gaines & asked for his number. I’m pretty sure I had already gotten it off of Facebook, but I needed a cover as to when he asked where I had gotten his number. Well he didn’t have his number – and the next morning at the late Wednesdays breakfast at Chickfila in the mall in which all of the cool popular people attend, Garrett made sure to announce to ALL THE COOL PEOPLE that I was asking for his number (it’s a good thing that I didn’t find this out until after the fact or I would have been utterly mortified). Cue in Sarah Straw – sister.

Wedding Proposal Ideas in Chicago, Illinois

So here I am thinking that Milton has a crush on me, when actually it meant some girl (me) had a crush on him. Oh well, who cares, because this was the best thing EVER! So I texted him, no clue what that text consisted of, but I’m sure I pondered what to say for a good 3 days. The best part about the whole shebang was that he actually responded! I think I cried (drama queen). Turns out he had a real crush on me too but was just too shy to do anything about it. We hung out a bit here and there but then biology happened (the class). His grades started slipping pretty drastically – like Cs (this is drastic to me)– so I had to help. We became study buddies and eventually on Halloween our senior year (Milton still claims its November 1st) he asked me to be his! What we didn’t know then, but the Lord had planned so perfectly, is that I’d always be his! He was by far the most kind, serving, gentle hearted guy & I knew the Lord had great plans for him, I just prayed I would get to be a part of them. Fast-forward 5 years and he continues to fulfill that prayer. He is still the most kind, serving and gentle hearted guy that in a few short months I get the honor of being his wifey!

Bride's Proposal in Chicago, Illinois

how he asked

The morning started off well, like the others had and would continue to on our trip in Chicago, IL. We got up, grabbed some breakfast and coffee, and headed back to the room. But on this morning, I had a surprise planned. Something months in the making that I had hoped she knew nothing about. I had built a ring, spoken with her parents, and set up an undercover photographer to catch the moment when I asked the big question.

But she had a surprise for me to. Much to my dismay, she readied herself and got dressed way too fast. I dragged my feet as best I could, but she was ready to go. You see, I had the photographer lined up to meet us at the Navy Pier at a specific time to catch the proposal and then have an engagement shoot. So we loaded up in the rental car with all of our things, ready for day full of things I had blatantly lied about (for a good cause). It was too early and on a whim, I devised a plan burn some time. I suggested we make a quick stop and check out my childhood home, neighborhood, and nearby beach. She conceded, however hesitantly. After a fast tour of Fort Sheridan, I exclaimed that we should get moving and go check out Olive Park near the Navy Pier. Again, she allowed it without question. I was beginning to push my luck. The drive went without a hitch and we were set for a timely arrival. I could feel my plan falling in line. That’s when the nerves began to build. We’re getting closer and things start to turn south. Our GPS can’t tell us exactly the turns we need to make. I made a left. Wrong. We went around the block, under one bridge and over another, changed lanes back and forth, got honked at once or twice, and made a right onto the Pier. Got it! But time is running out.

We found a parking garage, probably a half mile walk from the park. An expensive garage too. But I didn’t care because I knew that the clock was running down and we had somewhere to be. As we exit the garage and begin walking down the Pier toward the park, the absolute worst thing possible happens – rain. Only a little, but enough to make my heart race and my stomach clench. As we walk through the gates and along the rows of trees, Laura Jane suggests we stop for a picture, but I quickly brushed it off and suggested a better location, near the other end of the park. Again, she conceded. Very unlike her, I should’ve been suspicious that she thought I was up to something.

As we stood on the platform admiring the stunning view of the city skyline over the water, I tried to gain the courage and composure required to do what I’d been waiting for. I reached into my jacket pocket without her seeing, and held a small, secretive box behind my back, still unbeknownst to her. The adrenaline began to course through my veins, my pupils dilated, my body grew hot, my palms became clammy, and my breath quickened. I tried my best to appear calm. This was it.

After a few words, I dropped to one knee and, trying my best not to choke on my words, asked Laura Jane to spend the rest of her life with me! She cried, I think I did too, and gave an immediate “Yes!”. In the background was the photographer I had lined up, snapping away and capturing the moment that I made the best decision of my life.

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