Dorothy Heller

A writer, blogger, mother, medical interpreter, bookaholic, grandmother, shower singer, translator, tea-aholic and an aspiring songwriter. Still writing her novel and wants to write at least one good song.


It sounded like a good idea at the time to this mature boomer single woman. An invitation to an actual event from an online dating contact, instead of hours chatting virtually and not even sharing an actual cup of coffee in real time. A birthday party on a Friday evening for the owner of a restaurant in an upwardly scaling neighborhood.  He was best friends with this small business owner, he emailed me.  A birthday-party blind date instead of a coffee date–how bad could it be?

The gentleman looked tall and lean in the photo, and according to his dating profile, was educated and accomplished. I had high hopes.

Frank Sinatra’s High Hopes (not the Panic At the Disco song) is the title of an Oscar-winning song by the songwriting team of Sammy Cahn and Jimmy Van Heusen (they went together like a horse and carriage) from the 1959 film A Hole in the Head, in which world-weary single Dad Frank Sinatra finds true love and a second nuclear family. He charmingly duets with his child co-star about their “high hopes….high, apple-pie-in-the-sky hopes.” Retooled, it became the theme song for JFK’s 1960 presidential campaign, a highlight of the boomer generation.

I generally turn down events on Friday nights, unless the gentleman comes to pick me up. Friday nights are for collapsing at the end of an intense workweek to enjoy a few blissful hours of PBS Mystery and not having to drive, work, or even move. After five days of dealing with everything from stomach viruses to family tragedies, on Fridays I was ready to drop. But several well-phrased texts with correct grammar and syntax  had me in my car, heading for the rendezvous.

It’s the curse of the mature single—the self-blame when you give in to fatigue or inertia and don’t follow up on every possibility. How many true-life stories have I read about a woman finding her true love because just that one time she sucked it up and stopped hiding in the ladies room/went to the party/made the first phone call. If you don’t, you’re falling down on the job. Because he could have been the one.

At first glance, the gentleman was indeed tall, lean and neatly dressed, with a mane of distinguished gray hair. His movements were slow and careful-was it age, vision, arthritis? The first sign that something was wrong was when he started to enter the Thai restaurant right next door to our destination. He stood poised inside the entrance like a confused stork, his long neck swiveling, as he checked out the doorway. He finally recovered and we proceeded to his favorite Mexican restaurant and home away from home next door. My high hopes were beginning to deflate, like a balloon slowly leaking air. Unless I was mistaken, the gentleman was drunk–very drunk—one of those hard-core drinkers who appear dapper, upright and well-behaved, but are nevertheless plastered out of their gourds.

Once inside, he headed for the bar. Ready to plotz, I collapsed on a stool and ordered a dinner salad with extra chicken—the female mature single’s default dinner. I needed some energy to shlep myself home alone. He stayed ramrod straight beside me, as the bartender kept on topping up his glass.

My intoxicated swain identified the owner and his family to me—but never introduced me or spoke to them—and the birthday party was a cake that the owner’s daughter unceremoniously brought out during the busy evening.  Her family members were all too busy serving to stop and celebrate. My blind date further disgraced himself by righteously refusing a piece for both of us, preferring to drink his empty calories. A piece of the scrumptious-looking cake would have at least been some reward for the evening, however calorically unsound.

In between silence and sips, he tried to make conversation.  Of course, he  asked me about my work. “So, you work with illegals,” he replied, giving me a wink and leer, while surrounded by Latinos, including his “best friend,” not all of whose immigration papers he could have personally inspected. Meanwhile, the wait staff rushed around, serving him and the other drunken gringos.  “We’re all Friday night regulars,” he explained, as he sipped. He kept on encouraging me have to have at least one Margarita, “just a weak one.”

At home, I’ve been working my way through James Kaplan’s The Chairman, the second volume of his biography of Frank Sinatra. This more than 900-page volume serves a dual purpose—immersing myself after a hard day’s work in the trials and traumas of a superbly gifted musician and culture icon plus all the attendant gossip disguised as research—and as a convenient prop for weight lifting without having to get up from my recliner.

Biographies of creative people never seem to unlock the key of how they achieved their master works, especially when so much time and energy was devoted to boozing, brawling, and broads. Sinatra, in addition to being a musical genius who couldn’t read music, was a lifelong alcoholic, as were many of his most important lovers, friends and colleagues—Ava Gardner, Jimmy Van Heusen, Tommy Dorsey.

Sinatra is quoted as saying: “I feel sorry for people who don’t drink. When they wake up in the morning, that’s as good as they’re going to feel all day.”

Post-Eisenhower America thrilled to the alcohol-fueled adventures of the Rat Pack, originally founded by Humphrey Bogart, but made famous by the antics of Sinatra, Dean Martin, Sammy Davis Jr, Joey Bishop and Peter Lawford. The original version of George Clooney’s Ocean 11 and the 2018 all-female version, Oceans 8,  is Sinatra’s Rat Pack.

The celebrity banter of the birthday blind date and his friends consisted of tossing a crumpled dollar bill back and forth to each other because they were betting on the Cleveland Cavaliers versus the Golden State Warriors as they drank. They kept it going with great hilarity, even when the crumpled dollar bill ended up on the floor and they had trouble balancing themselves to bend over and pick it up without toppling over. There is no hope for romance for a mature woman when men choose to band together over their favorite bottle, sports team and each other.

Years ago, when Boomers were young and I had no idea I would ever become a mature single, I was in love with Frank Sinatra. I snuck up to the attic to listen to his music in secret; in my father’s home, only booming Beethoven concertos were permitted. Although I was hardly old enough to get my period, I was thrilled at the yearning and vulnerability beneath the tough guy façade. It worked for a while for boomer Mia Farrow, who briefly married him. After her horrendous divorce from Woody Allen, Farrow has called Sinatra “the love of her life,” and some suspect that Ronan Farrow is Sinatra’s son. One night on a bus in South Philadelphia, I saw a thin, depressed-looking man in a black suit, with the hat tilted at exactly the right angle and a cigarette dangling from his mouth. Could it be him? Fortunately, I chickened out. Mia was too young for him; I would have been “illegal.”

Suddenly, one of the drunken celebrants at the bar starts to sneeze and cough. Allergies, I hope. Documented or not, the bartender solicitously presents him with a pile of cocktail napkins like an attentive nanny so he can wipe up his streaming nose.

It wasn’t allergies. I’m still sick. It’s a high price to pay for a blind date.

During one Friday evening, I had gone through the entire Sinatra cycle—from High Hopes to Only the Lonely to One More for the Road …that long, long road.

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