Sharon and Dan Real Engagement Story

Written by    Last updated: August 21, 2006

Here’s the story of how I recently proposed to my girlfriend that I thought maybe you guys would find interesting. If there’s any chance of it making it on your website, please let me know.

My girlfriend Shannon and I have been together now for a little more than 3½ years and I’ve known for a while that she’s ‘the one’. I’ve wanted to propose to her for a while now but as one of the casualties of the high technology meltdown, long term employment has been challenging and finances have been tight so executing on my plan has taken longer than I would’ve liked.

Last April I landed a short-term contract and immediately decided that I was going to go ahead with the plan and started pulling together the details. Having tried many times in the past, I’ve known that Shannon is not an easy person to surprise. With this in mind I knew I had to think of pretty much everything in an effort to avoid her figuring things out.

Shannon had never been to New York City before and I had been many times. I’d fallen in love with the city and I knew it would only take one visit for her to feel the same way, and what better than to ask her to marry me all in the same visit!

My original plan was to surprise her at work, drive to New York (only 7 hours from our place), and once we hit the Canada / USA border, I’d fill her in as to where we were going. A good friend of mine told me though, that if that were the plan, she’d clue in quickly as to what was coming and he suggested I come up with a different plan claiming that we had won some contest or something as the reason for why we were going.

My boss at the time had to go to New York on business weeks before our pending trip so I used the opportunity to say he had won a contest through the hotel he stayed at and that he wasn’t able to go due to a prior family commitment that he was unable to get out of. I told Shannon the contest was for 3 nights accommodation at the Waldorf Astoria hotel, $500 spending money, and 2 tickets to see Mamma Mia on Broadway.

To help make things more convincing, I ordered New York tourism brochures off the Internet, plus I wrote a fake congratulatory letter from the hotel, addressed it to my boss, and stamped it with a ‘received’ stamp from the office to make it look like someone at the office had opened his mail for him. I signed the letter with a name I found on a press release off the hotel’s website and had a friend’s wife sign it for me so the signature didn’t look suspicious. I even sent a copy of the letter to my close friend who lives in another city, asking him if it looked legitimate enough.

A few weeks prior to announcing to Shannon about the prize, I wrote and forwarded to Shannon a fake email from my boss thanking me for completing a major project that I had been working on at the time and playing up how pleased he was with the work. The idea there was so when I said he gave us the trip and Shannon wondered why he would do that, I could tell her it was as a thank you for the work I did and remind her of the email I had forwarded.

I told Shannon about the prize on a Friday a few weeks later but intentionally left out some details and said we still needed to find out if the hotel would transfer the prize first before we knew we could go for sure. I figured if I told her all the details at once, it would look more planned and not very realistic so I held off on some. Then on the following Tuesday I called her at work and said everything was a go and brought home all the brochures and the letter. She fell for it hook, line, and sinker!

All along I had been saying we could just drive there, which in my mind was a cost-saving measure since I was already spending a lot of money on the whole trip but then she surprised me by saying we should fly so we’d have more time to spend in New York. Again, not to look too suspicious, I agreed and was lucky enough to take advantage of a seat sale with an airline on the last day it was offered. We already had another trip planned to go to Las Vegas and would return only 2 days before leaving for New York so I was a little concerned that she might change her mind as she wouldn’t want to leave our dog for that much time. Once I bought the airline tickets though, I knew she wouldn’t back out as it would mean throwing away $500. I started to get really excited figuring there wasn’t much that would stop us now.

So for weeks she was telling friends, family, and pretty much anyone that would listen, and of course I had to go along with it all thinking that if I told anyone the truth, something someone said might tip her off and get her suspicious. I thought for sure I was going to get struck by lightning for having lied to our parents and my grandparents!

So we headed off to New York on Friday of the Labor Day long weekend. I was pretty sure Shannon didn’t know what was about to happen but at the same time I didn’t let my guard down just to be safe. One worry I had was when we checked into the hotel she would be right beside me and say something when the person behind the counter quote the cost for the room and requested a credit card. In the end she didn’t think much of it and I quickly moved on and changed the subject.

A friend of mine that I worked with in the past lives in New York and is very well connected so he helped me with getting the theatre tickets and with a contact at the Waldorf Astoria. I wanted to talk to someone at the hotel so I could plan extra stuff to be set up in our room for when we got back after the big moment. Email is my preferred way of communicating and to be sure Shannon didn’t come across any emails beforehand, I created "going2propose@hotmail.com" as a private email address that I used for all communications.

The theatre tickets were left for us at the hotel’s business office and a note on our file when we checked in asked us to go there to pick them up. I opened the envelope only to find the name of my friend printed on each ticket and I thought for sure Shannon would know something was up. When I was working on a big project with this friend of mine years ago, I used to talk about him all the time and figured she would recognize the name. Turns out she didn’t think anything of it and didn’t make the connection. Phewww…  

Saturday was the big day. I snuck out of our room in the morning while Shannon was in the shower and made final arrangements with the hotel concierge’s help, and then we spent the day doing lots of sightseeing around town. Then later in the afternoon we headed back to the hotel to get ready for our big night. We started off at a very nice and romantic Italian restaurant (Shannon’s favourite) in Midtown Manhattan and just a few blocks away from the theatre. We each had the same meal, ordered wine, dessert, and cappuccino and enjoyed ourselves very much.

The ‘Mamma Mia’ show followed dinner, which was fantastic, and made us bigger ABBA fans for it. I bought a show program and a little teddy bear from the theatre as keepsakes and when that was over, we made our way up to Central Park where I took Shannon on a horse and carriage ride through the park. The trip lasted 20 minutes and about half way through I asked the driver to stop. Shannon figured it was so I could get out and take more pictures since I had been "camera-happy" the entire trip so far. I turned to her, told her how much I love her and that I wanted to show her just how much. I then got down on one knee (while still in the carriage) and pulled the ring out of my suit jacket pocket and asked her to marry me. By the time the words were out of my mouth she was already crying and she said yes- more like she nodded yes.

Once the ride finished, the driver took some pictures for us including some with his horse, which ironically was named Shannon as well, and then we headed back to the hotel. The arrangements I had made with the hotel ahead of time were to have a dozen of Shannon’s favourite flowers waiting in the room, champagne chilling on ice, chocolate dipped strawberries, and a CD player available. I brought with us a special CD that I made with all of our special songs on it and we danced, drank champagne and enjoyed the magical moment.

All throughout the trip I collected business cards, matchbooks, programs, receipts, etc. so we can create a scrapbook as a keepsake, and I also went back to the restaurant to pick up a copy of the menu too. New York is now "our town" and we plan on going back often to reminisce and remember that magical and special weekend. I love her with all my heart and look forward to sharing my life with her forever!

At this time we don’t have a date set yet and are considering different options for where and how to get married. It’ll be tough to top this but my hope is to have a wedding that is just as magical and special as the engagement, as Shannon’s worth every bit of it. We’ll see what happens…

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