February 25, 2013

A Chicago Rooftop Proposal



Tony Vega is Bespoke’s latest proposal success story. He lives with his now fiancĂ©e in Chicago, and took a few minutes to answer some questions for us.

Elizabeth Carter: How did you know you wanted to propose to Gina?


Tony Vega: I proposed to the love of my life on February 15th, 2013. A couple weeks earlier she and I decided it was time to take the next step in our relationship. We had been together since December 2011. To some that may seem like a short period but when you know, you know. I never really got that until I meant Gina, it’s something that people say but sounds like a myth or legend until you experience the love and trust we feel for one another.

At first the thought of proposing was nerve-racking. I knew it was something that every girl anticipates her whole life. I definitely did not want to disappoint her. Originally my thought was to do an all-day proposal, where we would have event after event planned after the initial proposal, keeping up the fun and excitement throughout the day. Our best dates have usually been all-day things, so I knew it was how I wanted to propose.

EC:  When you and I met, you already had this broad vision of how you wanted to propose.  How did you turn that vision into a reality?


TV: I had a broad idea of how I wanted the proposal to go, but they were just random thoughts, and I didn't have the first idea of how to take to make it all come together. Elizabeth helped out hugely here by giving me several options for each event, venue, etc. All I had to do was pick the ones I liked. At the end of the day I made the choices myself, but didn't have to do the grunt work of researching options, calling for reservations, speaking to staff ahead of time, and negotiating deals. I work 10-11 hour days and this all had to be planned in secrecy so there would just not have been time for me to do this all on my own.


EC: Describe how the day went for you. 


TV: In early February I contacted Gina’s boss and told him that I needed his help in getting Gina somewhere so I could propose. He came up with a plan that involved telling her she had to go to a networking event and should bring a date. I loved this because she called me a few minutes later, excited to invite me to the event. I laughed to myself as it began to fall into place.


Elizabeth and I chose ROOF, a rooftop restaurant atop the Wit hotel in Chicago as the spot where I would propose. Once we had made that decision, Elizabeth contacted the staff there, arranging all of our particulars. She picked out the most private, romantic area in the restaurant and reserved a table for us. She also arranged for two glasses of champagne, oysters, and a bottle of wine to be on ice for when it was go time.  We considered hiring a photographer to catch the moment, but settled on asking the wait staff to take photos with a camera I brought along, and they happily obliged. ROOF doesn't open until 4:00 pm, but Elizabeth arranged for me to get in early to set up. I showed up at 3:40 pm and met the restaurant manager, who escorted me to up the venue. Once up there, I met the staff and they showed me to our table in a very secluded part of the restaurant. They had put up a median wall so we would have no disturbances. Gina arrived at 4:15, right on time, and was none the wiser. She asked where everyone was and I said they must not have been here yet. She then asked if there was a coat check because she didn't want to have to carry her jacket around during the whole event. I motioned for her to put it at a very nice table which overlooked the city and had it's own fireplace. She was confused because that table was reserved, I told her yes it is, it’s reserved for us! I then began to give the speech I had prepared (with some help from this blog!) and got down on one knee. She said yes! 


From the Roof we headed to the Fairmont Millennium Park Hotel where Elizabeth had arranged for our regular room  to be upgraded to a suite with the most breathtaking views. We even had champagne and chocolate covered roses waiting for us as we arrived. Before letting Gina into our room I had her wait in the hallway so I could go in and light all the candles that I had placed there earlier that day. In addition to the candles I placed about 12 framed pictures of us from some of our favorite memories as a couple throughout the room and decorated the tables and bed with rose petals. I turned on the song “I Will” by The Beatles and called for Gina to come in. She was ecstatic! She loved everything, her eyes lit up when she saw the candlelit suite filled with photos from our relationship. 


Just when she thought it was over I told her to put her shoes back on as we had just five minutes to get downstairs for our dinner reservations at Aria, a renowned Asian cuisine restaurant in the Fairmont. Elizabeth had once again contacted the restaurant in advance to make sure we had a private table in a scenic section of the restaurant. Elizabeth suggested we have sushi for dinner because this is what we ate on our first date. After I decided to eat at Aria I remembered I had seen the exact sushi rolls we ordered from our first date in my ipPone at one point. I scrolled through my notepad app and found the exact rolls we had ordered that first night! Aria was able to create personalized menus with a message from me to Gina and had them placed at our table along with the roses we had prearranged.


The night was not yet over! After our fantastic dinner we headed to our room where we changed to our swim suits and went across the street to the Fairmont’s sister hotel, the Swissotel. We relaxed and swam in their 42nd floor pool while gazing upon the great city of Chicago. 


The night could not have gone better and it definitely could not have gone so seamlessly and smoothly if I did not have Elizabeth at bat for me! Thanks to her help we will have a lifelong memory that we will love to tell and never forget! 

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