Vicky and Jerry

Where to Propose in The Signature Room at the 95th

How We Met

Looking back, I cannot believe that I have known Jerry Moore for, what will be, seven years this December. At the time, I was pursuing a career in performance and thought that it may be a good idea to get some experience in the field. I auditioned for a show out in the western suburbs and met Jerry for the first time. No one could get me past York Road. Even then, the trek was killer for me! I saw Jerry in passing, but I wasn’t really interested in any way shape or form. He had a mustache. I wasn’t really into that. We didn’t really become friends until a little under a year later. This was when we started working on the show Dracula.

Both Jerry and I were cast as two of the lead roles in North Riverside Player’s production of Dracula. To be completely frank with you, I was a little nervous to be playing opposite Jerry. I didn’t really know him that well. He was also a bit older than me. Both of these things made me nervous. If you know me at all, you know I’m constantly nervous!

Over time, we got to know each other a little bit better. We laughed at a lot of the same jokes. We listened to a lot of the same music. We constantly had a lot of fun together. At the time, one of the other males in the cast was barking up my tree. I would flock to Jerry and talk to him. He made me feel safe, comfortable, and he constantly had me laughing.

During the show, we played opposite each other. We had to kiss in one of the scenes. After one of the performances, my director commented that the kiss continued to get longer and longer every night. It was evident that this may have been more than the well-known showmance.

The show came and went, but we continued to see each other and speak to each other as we patiently awaited our next show together. One cold January evening, Jerry professed his undying love for me… I kid. Really, he just told me he liked me.

After nearly 6 years together, we’ve been through it all. We’re both still alive to tell the tale. Since then, he has been my best friend, my confidant, and the love of my life.

how they asked

Jerry really isn’t a planner. I’m much more of a planner. Once we hit our 5 year anniversary, I told him that it was time that we shit or get off the pot. Well, he shat.

I knew it was coming. We hadn’t only looked at rings, but we had purchased one. The ring sat in my basement for months until Jerry made me put it in my safety deposit box. He said that I was playing with it too much. We purchased the ring in March, so I knew it was going to come sooner or later.

Jerry’s birthday is August 3. After I mentioned celebrating his birthday, he suggested that we go up to the Signature Room on the 95th floor of the John Hancock building the day after. I thought this was a bit strange. We were going downtown for his birthday on Friday, so why would he want to go back downtown on Saturday?

I knew this was not a birthday celebration, but instead, a proposal. Jerry knew that I always wanted my proposal to be at the Hancock Building. I know the show is a little dated, but I loved The Nanny starring Fran Dresher. Ever since I was a little girl, I wanted a proposal similar to Fran’s. Hers was at the Rainbow Room in New York City. Mine would be at the Signature Room in Chicago. It fit perfectly. Little did I know, I would be marrying my own, dapper Mr. Sheffield. Salt and paper hair and all!

My friend, Chessa, did my hair and make up in that Saturday. By 5 o’clock, we were in an Uber to the Hancock Building. Both of us were very nervous. Jerry thought he forgot his phone. I had been drinking champagne all day. I find nothing wrong with that!

We got to the Signature Room a little bit early. They let us sit down around 6:30. Our reservation was at 7. I saw the table. It overlooked Navy Pier. There was one single red rose placed on my menu and a bottle of champagne on ice.

I knew it was coming. Him and I had a couple drinks. We talked about the past, the present, and the future. Our future. Even though our dinner tasted a bit like frozen TV dinners, it was the ambiance and the company that made the evening fly by.

Proposal Ideas The Signature Room at the 95th

After dinner, Jerry said he wanted to show me a video. Jerry always wants to show me a video. Sometimes, it’s a funny video of a dog. Sometimes, it’s a clip from Honeymooners. You never know what you’re going to get with him. I put on a pair of headphones and I saw the outside of Megan’s house. He had prepared a bit from the movie, Love Actually. If you’ve ever seen it, it’s a beautiful film about how love can be unexpected and wonderful all at the same time.

Once the video was over, I looked to my right and I noticed year he was on one knee. In Rocky fashion, he asked me “What are you doing for the next forty or fifty years? You think you’d mind marrying me much?” At this point, I was in tears. As was he. We hugged. We kissed. We popped the champaign. First, there was a delayed reaction by the other diners, but after a moment, they clapped and cheered.

We got home, opened presents from my mom, and went straight to sleep.