Designed for Devotion: The Love Stories of the Upper East Side

Love has always found its way to the Upper East Side. Behind brownstone facades and Fifth Avenue parlors, some of New York's most famous romances unfolded, often shaped by wealth, ambition, and reputation. This winter we reflect upon the famous couples that have helped define New York’s cultural, social, and romantic identity. Their stories reveal love in all its forms: dramatic and discreet, fleeting and enduring, each story shaped by the city that surrounds it.

John Jacob Astor IV & Madeleine Force

No chapter of New York’s Gilded Age is complete without Colonel John Jacob Astor IV and Madeleine Force Astor. Their relationship captured the attention of Fifth Avenue society with its wealth, scandal, and tragedy.

The two met while summering in Bar Harbor and were engaged for a little over a month before their wedding in September 1911. Their hasty courtship and their age gap did nothing to dispel the gossip among Upper East Side society. To escape scrutiny, the couple embarked on an extended honeymoon to Egypt. Their travels were solidified into cultural myth when they decided to partake in the latest trend in transatlantic luxury travel: a trip on the Titanic. Madeleine was five months pregnant when the ship departed, and she would return to New York
a widow before her 19th birthday.

While the original Astor mansion no longer stands, you can still experience the Gilded Age of New York through other Fifth Avenue mansions that have been preserved as museums. For those seeking things to do in NYC in February, The Frick Collection or the Cooper Hewitt offers a glimpse into the world the Astors once ruled.

Morton Fullerton & Edith Wharton

Edith Wharton and Morton Fullerton’s love story unfolded quietly, shaped by the rigid expectations of Upper East Side culture at the turn of the century. Wharton married Edward Robbins Wharton in 1885, entering a union defined more by convention than affection. While their relationship was not driven by love, the couple filled their early years with travel, houses, and dogs. Edith first met Morton Fullerton in 1906 through a mutual friend, author Henry James. Fullerton, a worldly journalist for the London times, proved irresistibly alluring to Wharton, and the pair engaged in a deeply emotional affair that lasted three years. Although their time together was brief, Wharton would later consider Fullerton the great love of her life. He awakened an emotional depth within her that would go on to profoundly influence her work.

Their letters reveal themes of desire, independence, and the cost of convention, all of which would be heavily featured in her novel, The Age of Innocence. Wharton knew their relationship would never be accepted by New York Society, a world which was governed by restraint, reputation, and carefully observed rules. Wharton and Fullerton’s story speaks to the classic tale of forbidden romance, set against the Upper East Side’s polished facades instead of fair Verona.

Andrew Carnegie & Louise Whitfield

Andrew Carnegie and Louise Whitfield’s love story was one shaped by time, patience, and circumstance. The two met through Louise’s father, a longtime friend of Carnegie, and spent years in each other's orbit before becoming engaged. At one point they broke off their engagement due to Carnegie’s mother, whose dissenting opinions drove the couple apart, but their relationship never truly dissolved. 

After a period of separation, Carnegie and Whitfield renewed their engagement in secret, and only after the passing of Carnegie’s mother did the two finally marry. From the beginning, Andrew looked to Louise for inspiration. On their honeymoon, Louise suggested creating a grand music hall for all New Yorkers to enjoy. That conversation led to the creation of Carnegie Hall, one of the most celebrated landmarks for artists in New York City.

Louise played a pivotal role in shaping Carnegie’s belief that great wealth carried great obligation and civic responsibility. Together, they funded the creation of libraries, supported charities and established the Carnegie Corporation of New York. Their story reflects a quieter romance–one built on shared values, generosity, and a commitment that would quietly shape New York’s cultural heritage.

William S. Paley & Babe Paley

If America had royals, they would have been William S. Paley and Babe Paley. As the founder of CBS, William Paley helped define modern media, while Babe Paley became the epitome of Mid-century Manhattan glamour. Together, they represented a new kind of power couple that touted influence, taste, and a carefully curated public life.

Babe Paley was one of America’s most influential socialites, and her influence on New York fashion was unrivaled. She worked at Vogue and regularly topped “best-dressed” lists before being inducted into the Fashion Hall of Fame in 1958, deemed “above annual comparison.” Her impeccable taste came to define old New York glamor far beyond Fifth Avenue.

Their life together unfolded along Fifth Avenue at the intersection of politics, media, and fashion. Beneath the polished surface was a deeply complicated private life, a reminder that even the most enviable lives carry private realities. Still, the Paleys’ legacy continues to inspire, a rare chapter in New York City’s history where love, status, and influence moved in perfect step.

Leonard Bernstein & Felicia Montealegre

Leonard Bernstein & Felicia Montealegre shared the passionate, complicated love that can only be experienced by two artists. The two met in 1947 and married in 1951, beginning a partnership that would become inseparable from New York culture. Bernstein rose to fame as one of the city’s most celebrated icons in classical music conducting and composing, while Montealegre, an accomplished Broadway actress and activist, matched his energy with her own artistic and political pursuits.

Bernstein made his conducting debut in 1943 at Carnegie Hall with the New York Philharmonic Orchestra after a guest conductor fell ill. By the next morning, The New York Times had praised the young maestro as “a good American success story.” Throughout the 1950s, Bernstein did some of his most significant work on Broadway, most notably composing the iconic NYC-based musical West Side Story. Alongside him, Montealegre built a distinguished career of her own, performing in classical productions and appearing regularly on television. Together, they became one of New York’s most compelling artistic partnerships, blending music, theatre, and public life. Their Upper East Side home served as a cultural salon, a place for musicians, writers, and artists of all kinds to gather and share ideas.

Bernstein's influence is not relegated to history books. His legacy lives on in the warm glow concert halls where winter performances recall the joy of classical music. Across the city, winter concerts in NYC bring Bernstein’s music to life: emotional, immersive, and best experienced together.

Alexandra & Oliver

Today, a new generation of love stories is unfolding on the Upper East Side. Alexandra and Oliver call Brooklyn home, but escape to the city when they’re craving a fix of old New York.

Their afternoons are spent wandering through museum galleries, lingering over collections that span centuries, offering Alexandra a welcome change of pace from the contemporary art world that fills her working hours. Evenings unfold over intimate, candle-lit dinners before a cab ride to Carnegie Hall for one of the season's world-class performances. At the end of each day, after reveling in the city's creative spirit, The Surrey welcomes them home.

More than a hotel, The Surrey becomes their home base: a place to slow down, reconnect, and return to one another. In a neighborhood long defined by legacy and love, romance remains very much alive: old street corners bearing witness as new stories unfold, echoing those that came before.

From Gilded Age romances to literary affairs and philanthropic partnerships, the Upper East Side has long been the stage for love in its many forms. These stories have unfolded across Fifth Avenue mansions, concert halls, and the quiet residential streets that still characterize the neighborhood today. When the city grows still during the winter months, there is comfort in returning to a place that offers reflection and connection. The Upper East side remains more than a backdrop for love stories past: it is a place where connections continue to unfold, quietly and deliberately, season after season.