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When Shel Silverstein Made a Pass at Me

I lamented to my girlfriends that, though I do not approve of Harvey Weinstein and his company of men who sexually harass women, I felt kind of bad that I had never been approached by a man. But then I got to thinking that I really was approached by many men, just not as aggressively as the women whose approaches were more extreme. I’m reminded of Dorothy Parker’s saying that she made somewhere back in the thirties or forties: “Men don’t make passes at girls who wear glasses.” In other words, those of us less voluptuous are commonly not the target of aggressive men.

But men did make passes at me when I was younger. The one that stands out is the time when I was 27 and an intern at CBS in Chicago while earning my master’s degree at Northwestern University. My first job was to go the Playboy Mansion located in the swanky Gold Coast area of Chicago where Shel Silverstein lived and to get him to sign an agreement to allow his song “A Boy Named Sue” to be sung on a local program.

I called Mr. Silverstein on the phone. He started to make overtures toward me. “When can we meet?” sounded a bit ominous to me and I panicked for a week before I got back to him. Shakily I called again and made arrangements to have him sign the agreement. As a back up I asked my husband to drive me to the mansion. I even remember what I was wearing: a two piece print blouse and skirt. It was summertime.

With strict instructions to my husband, I got out of the car and opened the seven foot iron gate to the mansion, rang the bell and waited for Mr. Silverstein to answer it. Soon after a short, bald, bearded man with glasses answered the door and we stood in the entry hall while I handed him the papers. Apparently he had decided I was not worth the effort or else when he saw that I was a short Jewish woman who probably looked like his mother, he would go elsewhere to pursue his prurian interests. He quickly signed the papers and returned them to me without a glitch.

And that’s the story of when Shel Silverstein made a pass at me. In the years to come I would often think of him when I was reading “Where the Sidewalk Ends,” or “The Giving Tree” or “Lafcadio” to my children and my grandchildren. He still delights me though, no doubt, he probably had all kinds of sexual harassment stories to tell before he passed away.

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