Chicago · Lifestyle · Personal · Uncategorized

the story of my proposal…

It was a Monday.

Ryan had been telling me that his parents were coming into town for weeks. He said his Dad landed a huge account, and so we would be joining a celebratory dinner. I get off of work around 3pm – just to find out that the car is still with the mechanic. Meaning he can’t come and pick me up right now, so he offers to get my nails done in the mean time.

Obvi – I’m here for this! So I carry myself down Randolph to a nail shop that shall not be named, for I had an awful experience but that’s irrelevant at the moment. I get a dual french mani and by the time the UV lights flick off – Ryan’s there. We head home to relax for a bit, and I’m unwinding from my day. Meanwhile, he’s trying to rush me to get ready for this dinner. My fiancé is NOT a man that keeps to schedule dutifully. So it’s bugging me out that he’s being so insistent, but I’m trying to be supportive. So I throw an outfit together, since he demands that I dress for the occasion, and we head out.

He’s doing about 75mph in a 55 – and we pull into Navy Pier’s parking lot like children on ice skates. Ry says “We have to hurry up, jump out!” – and I’m looking at him like he has 4 heads because I’m in 4 inch heels and cant understand why we’re rushing to a restaurant. I see him reach into the trunk, only to emerge with a bouquet of roses. I try to take a moment to admire them – and he sheepishly admits they’re for me. But not right this second.

He’s begging me to hurry up, and I’m tip-toe running as fast as I can like a stripper from the cops – until I finally can’t keep up. I bend down and unstrap the heels – and we fly across the pier! To my amazement, we are boarding the FREAKING ODYSSEY – literally seconds before they close the gate for departure.  The hostess giggles as we run up the board walk, and she says “We were waiting for you!”

They escort us to a window table, and there’s a celebration card on the table. I finally ask, “Where are your parents?”. And he finally confesses that this was a surprise for our anniversary, so they aren’t coming. With the sun reflecting off the water, and my hometown just there on the horizon, I finally relax into the moment. Completely touched by the surprise, in awe of the immediate cocktails (because, YES), and in love with the ambiance. The Dj has smooth jazz spinning, and Ryan’s eyes are matching the water.

After we order dinner, he suddenly has to use the bathroom. During his absence, the waiter comes over to have my roses placed in the cooler. A little taken back that he could even see them under my chair in the dark dining room – but I’m a little buzzed at this point so I comply. Another 15 minutes go by – still no Ryan. And just before my patience runs out, he appears and asks me to follow him to the deck.

We are in the middle of dinner mind you – but I decide to just go with it. He firmly takes my hand, and leads me across the dance floor and up a flight of stairs. Just before we exit the door to the deck, he suddenly makes a left and drags me into this private dining room. Stumbling and a little annoyed now – he’s ignoring my protests and I’m wondering what the hell he’s up to. Until finally I look straight ahead….

and there – under a spotlight – there’s a canvased photo and my bouquet of roses. Before I can ask a question, I see him moving down to his knee… and I’m there. I’m in the moment I dreamt about late nights as a little girl. I can feel his nervousness, and my own warm tears falling down my face. He reads a promise to me, and we share a once in a lifetime moment. I said YES, and he doesn’t even put the ring on my finger right away because I have no clue how much time passed as we just held each other.

And when he finally put the ring on, that once belonged to his beloved grandmother, I felt the weight of the responsibility before me. I have no regrets. Afterwards, we went out on the deck and continued to bask in the moment. With the boat creeping back to shore, we felt a newness about the city.  And only the prospect of positivity and love lay before us.


&& that’s the story of my engagement. leave me a comment – or shoot me an email !

One thought on “the story of my proposal…

  1. Ashley honey, I got your beautiful “Save the Date” in the mail and just HAD to go online and visit your and Ryan’s website.
    I can honestly say that I adored seeing it … and after clicking on the link to your blog about how you guys got engaged…well, it sounds like it was just SO special and wonderful, I literally couldn’t stop the tears from falling!!
    Am just so excited and happy for you both. You are one lucky girl and he is one lucky guy!!
    It was such a joy to meet you in person at Ryan’s parents’ house Ashley, and I can’t wait to see you for the shower in July, and then of course, the wedding! I am saying prayers that you guys will have a super long and happy marriage. As of right now, I feel confident that you guys can weather any storm and thoroughly enjoy all of the good times 🙂 LOVE AND MISS YOU BOTH! -Aunt Laura


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