It was 11:35 pm on December 31st at the Chicago Hilton New Year's Eve VIP event when I asked my lady the most important question.


The night had been going amazing, the food was scrumptious, the music was generic but enjoyable, but most importantly the joy I witnessed on her face was everything. I am also grateful we had our friends with us—not only so we would have a great night, but also to help me set up the perfect proposal.


Little did my lady realize that throughout the night I would scamper off “looking for a shorter bar line” only to plead with/bribe every staff member in the hotel to try and get her and me up on a secluded, roped-off second-level balcony overlooking the event space to ask the question and snag a photo. Unfortunately, after working my way up from various floor staff members to event coordinators, I was informed it was impossible.


However, I wouldn’t allow this to dampen my moment. I had spotted this elegant lion head fountain in the main lobby of the hotel when we arrived and knew that would also be a perfect spot to ask her right before midnight. I made sure to let our friends know my plan so we could execute it flawlessly.


So, the time was nigh and the spot was chosen. With midnight approaching, I asked the party if they would like to get in line for the photo booth set up next to the lion head fountain. Anxiously I walked everyone over and set up in front of the fountain, we posed for a quick group photo and then I asked Emily if she would like to do a photo with just me. I got down on one knee and began my planned speech.


I got as far as “Emily Rose Herrington, these—” before my lovely lady cut me short with a series of “wait, what, are you serious” - each phrase being repeated and her tone rising with each repetition. Frantically, I grabbed my box, opened it, and asked, “Will you marry me?”


My lady looked at me with pure shock, stared deep into my eyes, and choked out, “The box is upside down.” PANIC! Realizing my fault, I flipped the box right-side up and again asked for her hand—her expression from before hadn’t changed, and for what felt like an eternity, I feared she would say no. Turns out, my lovely lady was so surprised, shocked and blindsided that her internal system had crashed and she forgot she needed to answer the question. Thankfully, after a quick reboot, she sobbed, “Yes!”


Proposals are one of those memorable moments in your life that hopefully occur only once. I think I pulled this one off pretty well and certainly made it memorable for both of us. I am so blessed to have my fiancée in my life and look forward to our journey together. See you at the wedding!

Original artwork by Brianna Garcia and Sebastian Broome