Proposal Story, (particularly beneficial if in NYC area)

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Aug 18, 2006
[note: the following is long, but good/thorough. If you''d like just the recommendations, skip to below the dotted line.]

Today was one of those special days during which I got to see my lovely girlfriend in the morning. Usually, I’m up and out the door before she even arises, as my day at the office starts early and I need to commute from the City to Connecticut via Grand Central Station. However, this Friday, the day needed to start off at home…

My cousin was in town since Wednesday on business. She informed me of her trip a while ago and also of her intent to bring her husband and stay a few days past the conclusion of business on Friday in order to relax, visit with my brother and me, and meet my girlfriend for the first time. The added benefit was the timing of it all – my parents’ birthdays fell on that very next two days (Saturday and Sunday), and so my cousins were going to take advantage of the serendipity and surprise my parents with a birthday visit (but starting on Sunday). Seeing as though my cousins live over 6,000 miles away and visits are rare, spending time with them was a special treat for everyone.

My cousin and I were in touch with respect to plans for getting together. My girlfriend and I live together in New York City, and my brother lives here too, just under ½ a mile from us. This was not the first time that my cousin was in town on business, but it had been a long while. Well, “in town” is stretching it a bit – she was in Westchester, NY, where she usually is if in the States. So, she knew of a wonderful restaurant that she wanted to share with us but the challenge was it was in Westchester. Given my cousin and her husband’s intent to spend Saturday with us in NYC, the challenge was resolved by me renting a car Friday morning, driving up to work in CT, then taking the 20 minute drive over to the Tarrytown train station to pick up my brother and girlfriend (they both work in NYC) after the business day. Then, we could drive over together to meet my cousins for dinner. Afterwards, we could all drive back to the City together and not have to worry about the train schedule, etc.

Unfortunately, the Hertz near us wasn’t open early enough for me to pick up the car and make it to the office in time for my morning meeting. And, I did not want to be stuck in traffic trying to dial into the meeting, only to lose connection. So, I elected to dial into the meeting from home, then pick up the car. Well, during this time, my girlfriend was getting ready for work. We were so glad to get to see each other in the morning. With the sun shining through a cloudless sky, and it being a crisp fall morning, the day was starting off wonderfully.

Before I knew it, it was the end of the day and time to pick up my brother and my girlfriend at the train station in Tarrytown. The day just flew. Given my brother’s obligations at work, he learned sadly mid-day that he was not going to be able to take the same train as my girlfriend, but was hopeful that he could catch a subsequent train and just meet us a little later in the evening.

I rolled up to the train station and pick up my girlfriend. She was impressed and surprised, a white Audi A6, that’s what I rented?!?! Wow! Well, consistent with my behavior in renting cars in the past, I always shoot for the best deals possible, and this time I did really well. I handed to her the directions to the restaurant and simultaneously typed the address into NeverLost, and before we knew it, we were there. My girlfriend was a little upset with me though (already!) because we were early and she wanted to drive around and see the area, it was so beautiful, with the leaves so many warm autumn shades and it being suburbia generally was relaxing, especially contrasted with home, i.e. NYC. I suggested that we see if my cousins were interested in driving around too, as that would be the courteous gesture to make. So we valet the car, walk in, and it turns out the place is a hotel too. We approach the front desk and state for whom we are waiting, to which the attendant responded that my girlfriend and I have been expected, and that my cousin called to say she and her husband are running about ½ hour late. The attendant kindly suggested that we could occupy our time either enjoying a drink at the bar or walking in the gardens in the back area. I pushed for the gardens, seeing as though we were at a high elevation and could likely see the whole of Tarrytown from where we were. So, she half willingly walked outside with me. We talked about who knows what. I offer to take her purse because it is heavy and she acquiesced. It was just a tad chilly outside but still cloudless, beautiful gardens surrounding us, and a view of the majestic Hudson River flowing at the bottom of the hill. We walk up a couple steps to achieve a higher elevation. I stepped down one step from her, as we often like to do, so that we face each other more directly (I’m at least a head length taller) and I take her phone. We need to talk, I tell her. There’s something I need to share with you. Look, my cousins are not going to be coming. I never even spoke with them, and they have no idea that we are here. My brother? He was never invited either, and he never intended to join us up here. It’s just going to be the two of us. It’s all been a big secret from you, but for good reason, I promise. The true reason we are here is because…

It was the perfect proposal.
It was also the start of an entire weekend together, little did she know, and it was all part of a Master Plan.

The goal of the proposal was to accomplish something memorable, fun, romantic, symbolic and a little bit indulgent. Let’s not forget it had to be a surprise, too. Here’s how it all went down:

The “cousins in town” was the perfect ploy. I could tell her way in advance, it occupied her entire weekend so she couldn’t make plans, and she was excited. Further, she had absolutely zero contact with them, so there was no way for her to express to them her excitement in meeting. In addition, the fact that my cousins were going to surprise my parents for their birthdays (they fall one day after the other) meant that my girlfriend could not talk to my parents about the cousins visiting, and neither could anyone else. Communication lines on the weekend were severed, and that is key to ensuring secrets do not get revealed. But what about my brother? Well, he had to be let in on it all – he is and was my confidant and rationale sound board throughout the planning.

The particular weekend I chose was doubly strategic – it was not just my parents’ birthdays, but it also was the weekend closest to the date when we were going to be able to see her parents, as well as my parents – an important consideration since both sets lived in other states.

Now, the ploy was set, but not without ensuring I could follow through with it. First, the ring-hunting. Over the summer and into early fall, I independently completed at least 75 hours of diligence before making the final diamond and setting selections. The most valuable resource, and in turn the winner of my business, was Good Old Gold in Massepequa Park, NY. Most important was the educational experience that they fostered. Additional factors included their demeanor (positive attitude, not pushy or forceful, excited to share/show) and the fact that I got to see and buy the diamond unset. It is very restricting to buy the diamond once it is set because you cannot fully appreciate its beauty – or as the case may be, its flaws.

Before making the ring purchase – a very large financial investment – I needed to ensure that I would have parental approval, or it would have all been for not. I flew down to see her parents – to ask them face to face. You become an undoubted winner in everyone’s eyes with an effort such as this. Down and back in a day, she never even knew.

Simultaneous with these above efforts, I had the place of proposal in the works. In the end, the winner was Castle on the Hudson. With hindsight, I can tell you that they nailed it – excellent décor and refined beauty, slightly opulent and indulgent, impeccable service (attentive and not overbearing). They earn additional points for working with me to hide my secret from my then-girlfriend, until the proposal took place (for example, the front desk attendant needed to say that my cousin called and was running ½ hour late…).

Flowers – I purchased a custom-made bouquet of flowers and had them resting in the middle of the bed. Flowers = happiness. Nice touch.

Music – Marvin Gaye is great. So is, at the right time, Frank Sinatra.

Dinner – The first night we drove to Blue Hill at Stone Barns. The food was great – not unprecedented, but great. The wine was excellent but unfortunately I do not remember it. The key to this event was dessert. My fiancé loves M&Ms so I had the company customize them and then drove a bag over to the restaurant earlier in the day and asked the chef to incorporate them in the dessert. Some M&Ms said our names and others said “together forever.” That was special too. Dinner on the second night was at the Castle, in their restaurant called Equus – they served a delicious meal and I would definitely recommend it as well.

Car – Through Hertz, I got an Audi A6, and have no reservations what so ever. What a great car.

Spare no expense my friends, this is a once in a life time event.


Oct 11, 2005
WOW, what a perfectly planned & romantic proposal!!!
Your fiancee is one lucky girl!!!! Congratulations!!!!!
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