“The first kiss and the first glass of wine are the best.”
― Marty Rubin
Writing this series has forced me to reassess my tastes. For decades, you could not have convinced me I was anything other than a Napa Cab guy—stubborn, predictable, and proudly narrow‑minded. Yet here we are. I hope you will agree my tastes are now considerably more diverse, or at least less embarrassingly provincial.
93. Taylor Fladgate Vintage Port 1955 – The first gift Gerry gave me was great, but it did not compare to two gifts she would later give me.
I must admit that I never had good luck with blind dates. Some were set up by people who clearly did not know me. Others were arranged by people who simply wanted to unload their friend or relative like a distressed asset. As I said, blind dates and I were not on speaking terms. Thus, you can understand why I was a little skeptical when a mutual friend offered to set me up on a blind date with this Gerry girl. What was wrong with her? Did she need a green card? Was she someone who could not string together a coherent sentence? I had already been set up with Quasimodo’s cousin, so I had checked that box. I was willing to take a date with this Gerry girl as an act of mercy for a friend. Think of it as my charitable work for the week. I just wanted to get the Kabuki theatre over with, preferably as fast as possible.
I called Gerry. At least she did not sound deranged. I told her I only had an hour because my friend Jeff, my brother from another mother, was getting married the next day. I was his best man, so I needed to help him with “important wedding things.” It was an admittedly pathetic excuse, but I needed a pretext to escape. Besides, I figured I could tolerate anyone for an hour. It was not a total lie. Jeff was getting married, and I was the best man. The rest was creative fiction.
The day of our date arrived: It was Friday, May 20, 1983. Jeff lived in Brooklyn, and we drove into Manhattan. We had been running all over the city doing pre‑wedding errands, such as pickups, last‑minute scrambling, the usual pre‑wedding cardio. Gerry and I arranged for us to collect her after she finished work.
Her office was at Federal Plaza in Lower Manhattan. At least she had a job. I confess that I was a little nervous. I just knew she was going to look like Shrek’s sister. Jeff spotted her first. There she was, standing on the corner of Worth Street and Broadway. She was tall, willowy, wearing a lovely dark blue dress with a floral print. Her hair was styled in a flattering pixie haircut. And she was attractive.
It suddenly dawned on me that there was a certain irony in picking a woman up on a street corner. (Relax, no trench coats, and nobody said, “You a cop?”) Still, I knew it would not take me long to find out what was wrong with her.
Jeff dropped us off, as he really did have to take care of some final arrangements for the wedding. Our date was down the street at a bar called Hors d’Oeuvrerie, located in Windows on the World on the 106th floor of the North Tower of the original World Trade Center. If you’re going to be nervous about a date, you should at least be nervous with a great view.
I was a confirmed bachelor. What on earth was I thinking? Temporary insanity?
This Gerry girl was certainly not what I was expecting. She was amazing! She was brilliant, funny, and, as my grandfather would say, someone you could rest your eyes on. I was hit by a thunderbolt. The hour slipped by too quickly, and Gerry sardonically asked me about my “appointment.” I was hoist with my own petard. I could slink away, kicking myself for blowing a chance to spend more time with her, or I could fess up and hope she would not throw her drink at me. Discretion being the better part of valor, I opted for the latter. Discretion being the better part of valor, I opted for honesty. I admitted my silly ruse and said I would love to stay, if she would. Miraculously, she wanted to stay.
We had a wonderful evening. We laughed, told stories, discussed travel, art, and other shared interests. I genuinely enjoyed myself. Then something else happened. I, who did not want or even like children, found myself thinking the unthinkable: Had I just met the woman I would want to be the mother of mine? I was a confirmed bachelor. What on earth was I thinking? Temporary insanity? Altitude sickness from being 106 floors up?
Time melted away, and Gerry said she had to leave to get home. She was an only child and lived with her parents. She had to take the subway to Penn Station in time to catch the last train to Long Island, where her father would pick her up about two hours later. This was a ritual she performed twice daily. I did my best not to look horrified.
Let me digress and tell you something about dating in New York. You’ve probably seen Sex and the City, but this is something they never explained, and you would not understand unless you lived in New York. There is something called “GD” and “GU.” GD stands for Geographically Desirable, and GU stands for Geographically Undesirable. Someone could be perfectly wonderful for you, but if she or he is too many subway or bus stops away, that is a deal breaker. New Yorkers do not do “long distance.” They do “two transfers and a brisk walk” at most, and that is practically a marriage proposal. This is why dating apps allow you to set a geographical limit on how far you’re willing to travel for love, because love is one thing, but taking the F-line is quite another.
Gerry was wonderful, everything I would want in a girlfriend, or dare I say it, a wife. Gulp! However, she did not even live in Manhattan. Long Island? Who lives on Long Island? (Locals pronounce it as one word: “Lon‑guy‑land.”) Long Island is where you have a second home, go for weekends, or spend the summer. No one lives there full‑time. And let me throw in one more thing: I was now living in Las Vegas. Talk about the ultimate GU!
I guess it is true what they say: Love conquers all. Somehow, I, who would not have gone more than five subway stops for a date, began traveling across the country each month to see Gerry.
Our first Christmas together was wonderful. Gerry had learned of my budding love for wine, so she gave me a special gift: a bottle of Taylor Fladgate Vintage Port 1955. She had gone to New York City’s venerable wine shop, Sherry‑Lehmann Wine & Spirits, then located at Rockefeller Plaza. It was known for older vintages and hard‑to‑find wines.
Sherry‑Lehmann, founded in 1934 shortly after Prohibition was repealed, closed in 2023 amid allegations that customers had prepaid millions of dollars for rare wines that were never delivered. The FBI raided the business, and the New York State Liquor Authority issued a cease‑and‑desist order after the shop failed to renew its liquor license, which is not exactly the brightest business strategy.
About 1,000 bottles have since been distributed to a small number of collectors. Even so, collectors, the landlord, and other parties have filed lawsuits over roughly 32,000 remaining bottles valued at $16 million.
Gerry did some research, and the staff recommended a Vintage Port. Port is a fortified wine, meaning that grape spirit or brandy is added before fermentation is complete. A Vintage Port is a single‑vintage wine, often aged for decades in bottle. The result is a sweet wine with flavors of caramel, butterscotch, chocolate, dark and red fruit, cinnamon, and other spice notes. It is often paired with strong cheeses, such as Blue Stilton, and served at the end of a meal, preferably after you’ve already impressed someone.
Taylor Fladgate Vintage Port 1955 is unique in that it was the only vintage Taylor declared in the 1950s and is considered “one of the most underrated vintages of the century.”
Port wines come from the Douro Valley region of northern Portugal, where wine has been produced for at least 2,000 years. Wine under the name “Port” was recorded as early as 1678. The Douro region became the first legally established vineyard area in the world in 1756, because the Portuguese were tired of amateurs messing things up.
Port is made from native Douro grapes such as Touriga Francesa, Touriga Nacional, Tinta Roriz (Tempranillo), Tinta Barroca, Tinta Amarela, and Tinto Cão. As many as 52 varietals can be used. They are often planted separately, then harvested and blended. Each varietal contributes its own characteristics. Being fortified, Port, like Madeira, has great aging potential. Some Ports have been cellared for more than 100 years.
Many notable Port houses have names such as Taylor‑Fladgate, Croft, Cockburn, or Sandeman—obviously not Portuguese names. These names are Scottish or English in origin. England had been the primary market for French wines in the 17th and 18th centuries, but the English and French were perpetually at war. England stopped importing French products, established embargoes, or imposed steep tariffs. It was one thing to go to war, but to give up wine would be quite uncivilized. So, English merchants set up shop in Portugal, because priorities are most important.
Producers also found that wine could not survive the long sea journey to England. But by adding brandy at just the right moment, they halted fermentation, leaving residual sugar. This fortified the wine, allowing it to endure the journey. The wine also picked up color and flavor whilst in barrels during the long time at sea.
Taylor Fladgate Vintage Port 1955 is unique in that it was the only vintage Taylor declared in the 1950s and is considered “one of the most underrated vintages of the century.” The fruit came from two Grade A vineyards about 20 miles apart: Quinta de Vargellas and Quinta de Terra Feita, each having different microclimates. Blended, they make a harmonious wine, unlike most couples who live 20 miles apart.
Gerry and I got married, and I, who neither wanted nor liked children, have been blessed with two remarkable now‑kidults.* Somehow, Gerry ended up with my Taylor Fladgate Vintage Port 1955 in our divorce. She definitely had the better lawyer (the cretin!). The upside is that Gerry and I have become friends again. I just hope she’ll let me open the bottle, preferably on a May 20th, the anniversary of the day we first met. If there is a better argument for marital harmony than a Taylor Fladgate Vintage Port 1955, I have not found it.
*Gerry and I have two wonderful kidults, Alejandro and Gabriela. Gabriela recently got married. I hate hyphenated relationships, so I now have a new son.
Saúde!
