Newspaper Personals Finding Love in a World before Online Dating

Before the Internet was invented, in the days of Operation Desert Storm, I met a devilishly charming private school teacher through a personal ad in The New York Review of Books. Since the publication catered to the literary set, it was a popular avenue for seeking culturally enhanced partners. In reality, it was just as likely you could meet a creep as a gentleman.

You might suspect that I tried every way known to a middle-aged Manhattan single woman to meet someone respectable and appealing, and was near the end of my trick rope. Singles parties, networking events, blind dates, bars, summer share houses, ski houses – nothing reaped the desired results, which was simply to meet an appropriate companion, preferably with a profession and not too much heavy baggage. I was tired of meeting the seedy and the unfaithful, the men who wore polyester in a city filled with style, or went camping in the Catskills, or who had custody of their hyperactive children.

Some of my failed encounters were a man with a clawed hand via New York Magazine, a good-looking New Jersey guy who said I was too corporate looking for him, but meant I was too old, and a 29-year-old lawyer named Mitchell, who was sexually attracted to older women. That first date happened after a fabulous blizzard when the city was virtually shut down. Wearing our Timberland boots and snow garb, we wandered chatting and hugging through a snow-laden, muffled Central Park, and then snuggled for hours in my bed.

There were plenty of married men in the mix, too, including a real estate developer from the suburbs. Now, he was appropriate, but had a wife. He bought me a pearl and onyx necklace with gold beads. Then there was the stockbroker from Rockland County whom I met with his second wife on a weekend in Fire Island. Randall was a cynical Viet Nam veteran, who had no qualms about infidelity. We had dinners in little Italian restaurants on Columbus Avenue during the week, and even a Saturday night date, when he was supposed to be chaperoning some Boy Scouts on a camping trip.

My therapist urged me to date married men, so I would lose my fear of abandonment. They were already taken, so there was no risk. Besides, the right single men were taken off the block almost immediately. My friend, Liz put it this way, “If you don’t give up, you might find a good one on the second Tuesday in October.” It really was all about timing.

So I ran an ad in the Review, which I had thought about doing many times. The first line grabber was: “Dimpled Redhead in her 40s – seeking someone to share life’s pleasures, a walk on the beach, Sunday brunch, Lincoln Center, and so on.” The only appealing letter I received was from a man by the name of David, written in a neat cursive, who turned out to be an English teacher at one of Manhattan’s most elite schools for boys on the Upper East Side. He was also the drama coach, in charge of directing Shakespearean plays in conjunction with the privileged young ladies at an equally prestigious girls’ school in the same tony neighborhood.

David and I met at a crowded 79th Street bar on the West Side, the Sunday after my youngest daughter moved out on me unexpectedly to go live with her father on Park Avenue. It took all my emotional fortitude to meet a blind date from a supercilious newspaper, when what I really wanted to do was run away to California and start my life all over again.

David was handsome in a Robert Redford sort of way and he called me Audrey from Shakespeare’s As You Like It. He said I had such pain in my eyes, which turned him on. If he hadn’t been so sexy in bed, I would guess he was slightly swishy, certainly dramatic and bent, playing mind games with me through the 6 weeks we spent together. It was an affair that I will never forget. I was 47 years old and he was 48. I have to say it was probably the last time I have ever been so madly in love to the point of being mad and sick.

Later my therapist would say it was because I was so vulnerable at that juncture in my life. The loss of my youngest daughter from my home was devastating. She was the daughter I had raised completely on my own, since her father had left us late in my pregnancy with this third child. Now, ironically, Jill was leaving me too. It was almost as shocking as when her father took off, except that he tortured me for more than a year in legal proceedings, while she just suddenly one Sunday morning, packed her bags and moved out to join her dad and his second wife, who happened to live around the corner from her school.

My two other daughters were in college, leaving me home alone in my three-bedroom apartment on the Upper West Side, the one I couldn’t afford but had bought anyway with a big loan so that they could have a nice place to live. During my life in New York City, I had gone from roommate situations to marriage to single parenthood. The house was always full with kids, their bickering and nagging. It may not have been easy, but it kept me busy and needed.

It was that fateful night that I met David, on my first night alone. He talked in deep-throated tones about solitude and Mozart piano concertos. I immediately took to this idea, ran out and bought as many versions as I could find of Concerto in D minor and stayed up late listening reverently to the tapes. I was determined to revel in my melancholy and loneliness. In a self-gratifying stupor, I succumbed to watching porno tapes solo, ordering Chinese food from First Avenue Wok, and reading The Woman’s Room for the third time.

One of my other saviors was graduate school at New York University in Greenwich Village where I was working on a Master’s degree in public administration, for which I’m still paying off the student loan. The program was incredibly time-consuming and mentally challenging, completely distracting me from my loneliness. David, as other men had done, razzed me about going back to school when I had a career in public relations. Several blind dates treated my graduate school ambitions like a menopausal condition.

Each night when I came home from school, David would call and in his moody, sultry voice would provoke me about different aspects of my life. He insinuated how needy I seemed to be. “I am drawn to you by the pain in your eyes,” he murmured time and time again. He was a drama king par excellence, a scoundrel who reveled in the misery of others. He was also a big fan of marijuana. It took me a couple of weeks to realize that most of the time he was stoned.

His best friend was a woman named Ruth, who had been married to an Irish lawyer who had left her for his paralegal. Like me, she was struggling to raise two children on her own in the city. Her son was a student at David’s school and they had a symbiotic relationship. David referred to Ruth constantly. “Ruth says I am only going to hurt you,” he was fond of saying.

It was amazing to me that David had existed the entire time I had lived in New York, since 1965, that we had lived only a few blocks away from each other, and how from one day to the next, he became the focus of my life. Of course, I knew that he could go out of my life on a moment’s notice, and I might never hear about him or see him again. This is the way it was in New York – you could love a stranger and he could disappear.

The first time David kissed me was in an elevator in an old established building on the Upper West Side as we were leaving a Thanksgiving eve gathering. “Your lips are as soft as a schoolgirl’s,” he whispered.

Despite David’s perfect looking body, he suffered from chronic wounds on his feet that did not heal. As the weeks went by our love grew more amorous, yet he would say things like, “My foot is worse when I’m with you.”

On Thanksgiving eve, I met his friends and then we spent the night at my apartment. In the morning, he challenged me, “Come home with me for Thanksgiving.” This meant a small town in Massachusetts, where he grew up the town football hero and something of a legend. I said of course not, I was going to New Jersey for the day to have turkey with my friends. My children were with their father.

He accused me of being rigid, said I should be able to act on whim, to let loose, to change my plans and go with the moment. I felt he was right and somehow got up the nerve to actually go to Boston with him that same morning. We went to the airport where he paid for two shuttle tickets to Logan and off we flew. We took a commuter train from the airport and he delivered me joyously to his widowed mother, an Irish, thoroughly proper lady, who had graduated from Wellesley College in the 1940s. Also present were David’s sister and brother-in-law who he detested and it seemed to be mutual. As the scotch whiskey went through too many rounds, the brother-in-law scoffed disgustedly under his breath, “What a lush.”

At bedtime, I was assigned to the first floor guest room while David was sent up to his sparse childhood room, filled with boyhood trophies and memorabilia. After Mama went to sleep, he came to my bed, but soon fell in a drunken haze on the twin bed across the room.

How can I explain this perverse attraction to a man that was toying with me, yet seemed to love me? Though my childbearing years were over, my romantic fantasies had me walking on Third Avenue with a baby stroller.

I never wanted that weekend to end. We opted to take the train back to Manhattan, because said David, “I want to make this last as long as possible.” Those minutes and hours that we rode through Massachusetts, Connecticut, and finally New York, were the most poignant hours of my life, certainly the most awesome experience I ever shared with any other man, just riding on the rusty old Amtrak. We talked the entire way home and in the train window, I savored his reflection. I would turn to him periodically and look into his crystal blue eyes and my heart was so filled with love, I wanted that train to go on forever.

Back in the city, he resumed his games with me – calling at the last minute and asking me over and taking me to exotic little neighborhoods. One frigid night in December, on a trip to little India in the East 20s, we walked up Second Avenue and we could see the breath from our mouths. I will never forget when he said, “You know, I really do love you. Don’t you think I’ve thought of every possible scenario?”

But in the end, he couldn’t deal with the relationship and destroyed it. It reminded me of Robert Redford (Hubble) and Barbara Streisand in “The Way We Were.” It just couldn’t be. He was after all, the blond New England Yankee, who taught private school on the Upper East Side and lived in a walk-up apartment; and me, the too nice, too affectionate, too needy girl from Chicago who wanted desperately to find her soul mate.

So one night David ended it. “We can’t just spend our lives hugging each other,” he said. He told me he had met someone else. Of course, it was a lie. Really I believe he went back with his old girlfriend who he knew from his glory days outside of Boston. She was a professor at Harvard working with a famous psychologist who was an authority on adolescent girls.