VINTAGE GOSSIP - An Unescorted Woman
By Amy Phillips Penn
“Tom has a theory that homosexuals and single women in their thirties have natural bonding:
both being accustomed to disappointing their parents and being treated as freaks by society.”
– Helen Fielding, Bridget Jones’s Diary


I love to go out alone — it’s an adventure, a potential conquest, and who knows what mystery might prevail. Of course, like so many adventures in life, this one is conditional.

When I go out alone into the anonymity of night, I wander into a place where absolutely no one is likely to know me.

Like all good Freudian or Jungian neuroses, this bravado-not goes back, not to my childhood, but to my dating years.

In the course of interviewing dozens of women who were quite independent and ahead of their times, I am reassured that I am a quiet part of a kick-ass unescorted women’s collective unconscious.

Women in the seventies and eighties were not comfortable going out to a restaurant or bar alone. Simply put, it just wasn’t done.

A friend’s mother told her that women who went out by themselves were considered whores.

I just felt like I would be construed as a loser.

On dateless evenings, it was much cozier to stay at home.

Going out alone meant you would have uninvited company in the form of an overpowering anxiety attack that no paper bag could quell.

An anxiety attack by any other name is still an anxiety attack, and the best elixir for one is to occasionally to avoid reality. Denial can be a girl’s best friend. Embrace it.

Life often seems like a series of relationships, interrupted by breakups or vice versa: it’s that glass half empty thang.

When I first got divorced, I was fresh out of male escorts to take me out and prove that I had no visible dents. What to do?

In time, I developed two close male friends. Bliss.

I could go anywhere with them. We would all have our eyes out for a potential “someone special,” or at least not visibly psychotic.

We had rules. If one of the men were about to run off with a Playboy Bunny (they wished), they made sure that I was safely ensconced in a taxi. They even wrote down the cab’s license plate number. Coddle me once, coddle me twice, and coddle me again.

“They say that all good things must end, autumn leaves must fall.”

And crash and fall they did.

One of my best buddy male friends got married, and I’m sad to report that the other one drowned. He was in his forties.

I was on my own again.

I watched as my girlfriends panicked as to what escorts were available for predictably boring parties. A close friend invited her male bestie out to Southampton for the weekend. When word got out, her mother’s neighbor called frantically and asked if Alfredo could come to her dinner party. She needed extra men. It seems that Southampton dinner parties always needs extra men.

My friend Wendy was not even mentioned much less invited.

In time, I grew bolder.

Life became somewhat easier for women, who didn’t have built in escorts, walkers, or husbands. I could go to the nearby Mexican restaurant with a girlfriend, but Le Club or Doubles was not on the radar.

One night, when I really wanted to go out and had no partners in crime available (male or female), I challenged myself to venture into uncharted territories.

I wandered in and out of bars with Irish names in the East eighties.

A table basketball game was going on. I shimmied into the spectators spot to blend in.

Someone made a basket. Someone broke a glass.

I left with the man who made the basket. It was somewhere between March 31 and April Fools depending on what watch you were wearing. Think pre-digital.

We found a sushi bar that was opened late and were the only customers left in the place. The sushi was good, the night was still young and…the owner of the restaurant was having a fist fight with a client right in the middle of Second Avenue.

We made an attempt to pay our bill, but police sirens were looming, and the owner didn’t see too concerned.

The man I met was a Harvard graduate, and one of the first high school NHL draft picks.

We lived together for eight years.

When we went our separate ways, I took a deep breath, and wondered where my next solo adventure would take me in my high heeled odyssey.


“The fact is, sometimes it’s really hard to walk in a single woman’s shoes.
That’s why we need really special ones now and then to make the walk a little more fun.”
– Sex and The City

Leave a Reply