The Proposal: HIS Side

To ask for a woman’s hand in marriage is a big deal. Obviously. Hell, I can even get a little misty watching Monica propose to Chandler in a room full of 50 million candles. So I really wanted to make the proposal special for Wendy. Short of spending money I didn’t have and flying us to Florence for a long weekend, I knew it had to be in New York City. Though we met, fell in love and spent most of our time in and around Boston, NYC has been ‘our place’. The first summer we began dating we took an amazing trip to visit Wendy’s friend Lauren and explored the city together.  It was our first trip together and definitely brought out a passionate love for all that the most famous city in the world has to offer and we’ve been going back ever since.

Now, we had obviously had discussions about getting married. And I had listened and paid attention to anything she said about jewelery or friends or celebs’ rings.  So it was not going to be a full on, out of nowhere surprise.  Additionally, Wendy knew that I knew that we both love the Christmas season. So when I told her I had bought tickets to the Radio City Christmas show in early December, I knew she would be a little suspicious.  I went into deception mode. I downplayed anything to do with getting engaged. I tried my damnedest to make it so that going into the first weekend of December she would actually be a little disappointed leading up to the NY trip because we most likely wouldn’t be getting engaged in New York, where we both separately knew was where we both wanted it to happen.

Here were the lies I told to my fiancé for the weekend of December 4-5th 2010: We would be driving down to NY Saturday morning with enough time to enjoy some of the city’s Christmas spirit for a couple of hours during the day. Possibilities included ice skating, a quick stroll up 5th Avenue to look at windows, or maybe a very quick trip to Macy’s. We would grab dinner at a pub-like restaurant in the theater district. Then would go see the Radio City show at 7. And after would go home to my parents in Connecticut that night.

Here were my actual plans for the weekend of December 4-5th 2010: We drive down in the morning from Boston. I subtly guide Wendy to walk up to the Central Park area with likely detours along the way on 5th Avenue, the Park Plaza, and possible ice skating all within the fake time constraints of the fake plans for the day. I’m not a good liar, so all of these deceptions building up on top of each other were not only hard to remember, but almost as stressful as knowing I was going to propose within a few hours. Instead of a quick dinner and show, we actually had nothing planned but a long relaxing dinner much later in the evening, and tickets to the afternoon show on Sunday. With an overnight stay at a hotel that I couldn’t tell her about or else she would absolutely be suspicious that something was afoot. So actually I was more worried about trying to cover all my lies than the actual proposal.

As we walk through the city, all I am thinking is, get to the Mall in the park. And Wendy wants to explore everything. We go in stores, we walk around the Park Plaza hotel. The one thing I was counting on was ice skating, but we decide against that. So at this point comes the tricky part for me. With fake limited time left in the day due to our fake plans, it would have made logical sense to head back down towards the theater and get food. Luckily, my casual mention of “Oh do you want to go check out the Poet’s Walk area “ is agreed to and we approach the place where it’s all going to go down in my mind.

Back track a little bit, and get into my mind. Unknown to pretty much anyone, a few months before I had actually been down in the city alone, and had scouted the area out for where I wanted to propose in regards to best location along the Mall for photographic purposes (i.e. trees in the background, benches, less people etc). I had contemplated sneaking our friend Louis down to secretly capture the moment, but knew that timing and logistics would make it impossible to know when exactly it would happen. And I wasn’t going to have him waste his weekend during the holiday season freezing in the park alone. So I was set on trusting a stranger to be able to use my camera to take some pictures of the proposal as it was happening.

We are walking, and walking, and I’m getting tense. I keep looking at sketchy person after sketchy person walk by. I’m just searching for someone that looks like they will a) be competent enough to take a decent picture b) not take off running with my camera. And it couldn’t have worked out any better. After walking for what seemed like eternity, and definitely throwing Wendy off any scent of it happening, I see a guy walking with a woman who looks like he won’t screw this up. I ask him if he would take a photo of the two of us, loudly enough so that Wendy can hear. Then I turn my back to my future bride and whisper to him that I am going to propose and could he take as many pictures as possible. I had hid the ring in the camera bag (which I had obsessively touched 527,000 times to make sure it was still there during the time we walked around the city) and turned around and got on one knee. The next 10-30 minutes are a big blur of joy, relief, kisses, texts, calls, and smiling.

Most importantly, she said yes. The man who took the pictures got some great ones, and it turns out that he and his wife had gotten engaged in just about the same spot 9 years earlier! We had a wonderful engagement/Christmas weekend in NYC. And I didn’t have to lie anymore to my future wife.



  1. hahaha very nice recap (you big liar, you)!! I’m glad you didn’t make Louis hide in the bushes all afternoon 🙂

  2. Hilarious Brian! What an enormous amount of planning ..and worrying…it’s amazing, really, how it all came together. You did a great job! You had all of us guessing..and I know Wendy was thrilled with your efforts.

    I’m so glad you shared the details! Your re-cap is excellent. I knew she was in good hands…now that I know how meticulously you can handle enormously stressful situations, I realize she is in extremely capable hands! I couldn’t be happier for the two of you!

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