Wedding Proposal on Ice

This wedding proposal on ice may just be the cutest proposal you’ll ever see (and the story below is just as amazing!).

Heather and I shared our first date on the ice-skating rink at Bryant Park on a Sunday afternoon in late October 2006. Though that day would impact both our lives, we had never been back since. Some would say I’m somewhat nostalgic, so it seemed only right that we return to the place it all began to take the next step in our lives together. Since the rink at Bryant Park is only open during the late fall and winter months, my options were somewhat limited. I knew that I needed at least two months to plan efficiently for things to effectively fall into place and without suspicion. Hence Sunday, November 28th, 2010 was chosen.
Now that I had the when and the where secured for the engagement plans (and I was fairly certain of the who and the why), it was time to work on the how.

I believe when a man asks a woman to be his wife, that moment encapsulates more than just those seconds surrounding the words “will you marry me”. I feel that instant is the culmination of the millions of moments a couple has shared leading up that point, a journey if you will. The following are a few memorable “steps” in our journey together that helped shape that Sunday afternoon…..

  • A few weeks into our dating, I decided to make Heather dinner at my place and dazzle her with my expertise in the kitchen. Throughout the night, Heather took special note of the Winnie the Pooh Cels and other Disney artwork that adorned my apartment walls. Soon after, Heather created a variety of pet names for me, including PB and more so Pooh (bear). A name Heather still uses on a daily basis.
  • On our first Valentine’s Day together, I gave Heather a purple (her favorite color) plush Winnie the Pooh Bear. He is never far from her bedside.
  • About four months after we met, Heather and I visited Panama during its Carnival celebration. While there, my fair skinned French-Irish girlfriend found herself basking in the sun, soaking up those Central America rays with one minor detail eluding her: suntan lotion! From that moment on, Heather became known as my little Lobster.
  • As a native Chicagoan, I am, have been and always will be a Chicago Cubs fan. As a native New Yorker, Heather is a fan of the New York team not named the Yankees.
  • Heather has two adorable tattoos. One is of the Latin phrase “faith, hope and love”.
  • Written poetry and other charming quips were some of the first ways I expressed interest in Heather.
  • 2010 marked the fourth year Heather and I had been a couple. This was the origin of the four alter-ego “Pooh” bears.
  • I am the east coast director for the non-profit organization “Give Your Sole”. Often, I attend various running events to collect shoes for those less fortunate.

So, I contacted Upsilon Ventures (Citi Pond’s marketing company) in late September to discuss the possibility of implementing my proposal in Bryant Park in late November. After securing the details for the 28th with the rink manager, it was determined that Amy Biletto was going to be the liaison between my project and Citi Pond. It needs to be said that this could not have happened without her assistance.

I had asked that Amy begin emailing my cousin Amanda in early October stating that her name was drawn to host an ice-skating party for twenty of her friends sometime during the month of November. The two then spent the next three weeks exchanging emails trying to set a date and time that was ultimately always going to be at 2:30pm on November 28th.

I had all emails filtered through me so that I could properly set the stage and put forth a few key details about the upcoming ice-skating party: that guests needed to arrive at the rink by 2:30 on the 28th and that because this was a promotional party, the host might be asked to wear a microphone and the event may be filmed.

A few weeks prior to the 28th, I then had Amanada contact Amy stating she had to work last minute that day and couldn’t host the party. Amy then replied that the date couldn’t be changed, but she could offer the party to a friend to host in her place. Amanda then forwarded the month long chain of emails to Heather asking her if she wanted to “host” this ice-skating party. Heather graciously accepted the opportunity from Amanda.

Heather brought the party to my attention and I reminded her of my Give Your Sole commitment that day. I said I could join the skating party after the race in Central Park, however, so Heather began to send out the invites to her newly won ice-skating party.

I had spent most of October conceptualizing the alter-ego Pooh bears and individualizing signs to correspond with each of them. The final result was the following: One purple Pooh – Heather’s favorite color and nightly companion. One blue Pooh – my favorite color and a common color of both of our favorite sports teams. One Pooh wearing a straitjacket. One green Pooh donning a thief mask and bearing a striking resemblance to Cupid. One normal Pooh. And one Lobster!

Once the costumes were fashioned and ordered, it was time to work on the signs and the accessories that would accompany the Pooh bears. The signs were painted during the day when Heather was at work and stored in our front hallway in a box that was labeled “Give Your Sole” supplies. Surprisingly, they sat in our apartment disguised for nearly a month. Heather simply thought they were the tent and awning I was to use for the race in Central Park on November 28th.

Thanksgiving weekend came and Heather went to spend that time at her parent’s house in South Hampton. I made sure that her mom kept Heather away from NYC until Sunday morning when they would all come into the city for a family dinner and some Christmas shopping. My mom and sister Kim also had planned on coming to NYC that weekend for a quick getaway before the winter holiday.

On Sunday, November 28th, I arrived at the rink around 11am to set things and do a full costume run through with the signs and characters. I also wanted the characters to experience what it was like seeing with the costume heads on. As the audience and Heather would be able to see the writing on the front of the signs, on the back were cues prompting the characters to react and perform accordingly.

Heather and her friends arrived at ten past two that afternoon with the majority of her party in attendance. In keeping with the “promotional’ status of the party, Heather was introduced to the two videographers that were hired to play the role of the marketing department employees of Citi Pond. They set Heather (who was somewhat reluctant) with a microphone and began to document the afternoon, as it was about to unfold.

At 2:45pm there would be an announcement for all skaters to clear the rink for the cleaning of the ice. My sister Kim and my cousin Amanda (who at the last minute said she didn’t have to work) would be skating with Heather when Amy (my Citi Pond liaison) would signal Kim about a minute before the announcement was going to be made. Kim would then signal Tara (Heather’s sister) to corral Heather’s party guests to not leave the area just outside the ice rink when the announcement was made. Kim was then to skate herself into position with Amanda and Heather at the far end of the rink and fake a fall on the ice. This time was needed to make sure no one would be on the ice when the characters entered the rink. I had also strategically placed five friends throughout the surrounding the park with FlipCams to catch any action the videographers were unable to capture. The skate guard who attended to Kim’ “falling” was there to aid in delaying the trio while I set up the signs and position settings for the characters on the opposite end of the ice.

Cue Frank Sinatra over the intercom….. enter the characters. What unfolded henceforth was (as they say)…. the start of our happily ever after.

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A little side note about Heather’s ring. I wanted it to be a unique and special part of our day and our life. There was a quote that was shown to Heather a few years ago about love. It was, “more than yesterday, less than tomorrow”. We discussed the meaning of the phrase and both found it deeply moving. I told her it means to me there are two days out of the year that love is not perfect: yesterday and tomorrow. We only have today. Heather’s birthday falls on the 16th of February (2/16). For that reason, the ring was created for Heather having a center stone of 2.16 carats and a surrounding setting that included 1.47 carats. Thus equaling 3.63 carats (two days less than a year). A constant reminder that there are two days out of the year our love might not be perfect, we only have today – yesterday and tomorrow are not promised.