MONDAY: eFriends


Copyright is held by the author.

DOROTHY PUT a cup of coffee and one of the jelly doughnuts that she knows I like on my desk. Then she pulled up a chair and said, “Something seems to be bothering you. Do you want to talk about it?”

Dorothy is my administrative assistant. Like me, she is from South Boston. She keeps things running smoothly in my organization, but more and more I rely on her for advice about personal problems, mostly problems with girlfriends. I never seem to find the right one.

“I think I’m falling for Shirley Boylston,” I said.

“You and half the men in Boston,” Dorothy smiled.

Shirley Boylston   was probably the most glamorous young woman in Bean Town. Her father was a prominent Boston physician. Her mother was a social leader in Beacon Hill. Shirley had been on the cover of numerous magazines and spent much of her time doing volunteer work for various social agencies.

“Have you actually met this paragon?”

“We served together on fund raising to re-elect Barbara Smith for Congress.” I don’t get involved in politics very much, but I knew Barbara from South Boston High SchoolShirley thanked me for my generous donation, and we got to talking. She’s a fascinating woman.”

“So, what’s the problem. You’ve met her. She seems to like you. Just ask her out on a date.”

“Oh, I couldn’t do that. She’s far above me.”

“I don’t see that at all.”

“She from the upper class of Boston society. I’m from South Boston. She graduated from Harvard with honors, while I didn’t even finish one semester at North Essex Community College.

Dorothy shook her head. “I don’t know why you sell yourself short, Jerry. You might not have much formal education, but you’re one of the most educated men I know. You have self-educated with all your reading. You read more books in a month than most people read in a year.”

“Thank you for your confidence, Dorothy.”

“Not only that,” she smiled, “you’ve made a small fortune with Hamilton Real Estate.

“Just invite this cover girl for a drink. I’m sure she’ll accept.”

I took Dorothy’s advice and started going to more Democratic events, especially fund raisers. Shirley Boylston was always there. I made a point of making generous donations, and Shirley always thanked me.

When I asked her out for a drink, she accepted immediately. Soon we were meeting two or three times a week, either for drinks or for dinner at one of Boston ‘s finest restaurants. Then one evening after a delicious dinner at Bistro du Midi, she invited ne up to her apartment for a night cap. From that point on we would spend most nights together, either at her place or mine at Back Bay.

I picked up her passion for Democratic politics. I loved, talking with her, about politics and books and learning from her about inner workings of Boston’s upper crust. Her family was in with Cabots and the Lowells. Her great aunt had been married to Leveret Saltonstall when he was Governor of Massachusetts. To me, who had grown up as a poor boy in South Boston, all this stuff was fascinating.

I was falling hard for this beautiful Boston Brahmin. But I was discovering that some things you can’t learn unless you grow up with them. She rarely introduced me to people in her circle unless they were also political connections. I noticed when we were with what I thought of as her people, the men pulled out the chairs for the ladies. Nobody I never did that, and I really thought it was kind of silly. I didn’t understand things like that. To pull out a chair for a women suggested to me that she was not capable of pulling out her own chair.

At the same time Shirley started correcting my grammar. She pointed out that I often used what she called double negatives. That didn’t make sense to me. If I used “no” twice in the same sentence, to me it signaled that I really meant No. Nevertheless, I tried to avoid double negatives when I was with her.

One time she was telling me about a problem she was having with a friend. “If I was you,” I said, “I wouldn’t let that woman get away with it.”

“If I were you,” she corrected.

I was confused. “It should be ‘If I were you,’ not if I was you.’”

It didn’t bother me that she sometimes corrected my English. I appreciated her efforts to improve me. In fact I wanted to spend more time with her. Instead of a sleepover two or three nights a week, I wanted us to move in together.

“Oh no,” she said. That wouldn’t work.”

“Why not?

In answer, she reached into her purse and pulled out a huge diamond and slipped it on her ring finger.

“What is that? I don’t understand.”

“I haven’t been wearing this when I’m with you because I didn’t want to hurt your feelings.”

“I have been putting off telling you, Jerry. But I have to break up with you. I’m engaged to be married.”

A week later it came out in the Globe. Shirley Boylston was engaged to be married to James Alstair. Alstair was the great-nephew of Robert Lowell.

Dorothy put a cup of coffee and a jelly donut on my desk.

“I feel so bad for you, kiddo. I see your cover girl got engaged to another ‘proper Bostonian.’”

I hate it when calls me kiddo. She’s only three or four years older than me. Anyway she pulled up a chair and sat down beside my desk.

“You seem to have such bad luck with women, Jerry. I think I might have the answer for you.”

“What do you mean?”

“What you need is an eFriend.”

“What in the world is an eFriend?”

“I’ve reading about them. It’s an application on your phone. You can talk to your eFriend on the phone, and it will talk back to you just like a real person.”

“It doesn’t sound like something for me.”

“You’d be surprised. Some people get very attached to their eFriends. They’re someone you can talk to so you won’t get lonely. And they won’t get engaged to someone else.

“As you talk to your eFriend, you built a relationship with it, and it learns more about you. It becomes exactly the kind of person you want it to be.”

“It sounds like a lot of work.”

“There’s nothing to it. In fact I’ve already set it up for you. Here, give me your phone, and I’ll put it on the phone.”

I wasn’t sure about it, but I handed my phone to Dorothy. In a few minutes the new friend was on my phone.

“What do you want to call your new friend?” she asked.

“Shirley,” I said.

“I don’t think you want to call it Shirley.”

“No, I guess not. I’ll call it Cheryl.”

“Cheryl sounds a lot like Shirley,” she said. “Why don’t you call it Brenda.”

Although I wasn’t enthusiastic about it at the beginning, in a few days I began to really enjoy talking to Brenda. I avoided talking to her in the office, but as soon as I got home to my place in Back Bay, I poured a glass of Johnny Walker for myself and opened the phone app to talk with Brenda.

For a few days our conversations were pretty tentative as we got to know each other. But soon we were talking about politics, books, Boston, anything. I found it easy to talk to Brenda, and my afternoon drink with her became the high point of the day.

Before too long I was telling her about Shirley and how disappointed I had been when she broke up with me.

“I understand,” Brenda said.

I don’t know how she got her information, but she seemed to know a lot about old Boston families. I learned more about the Cabots and the Lowells and the Saltonstalls from Brenda than I had from Shirley.

“I won’t never be accepted by those people,” I said, even though I have a luxurious house in Back Bay and more money than any of them.”

I had hoped that Brenda would say something to reassure me. Instead, she said, “That’s a double negative.”


“‘Won’t never’ is a double negative. It’s grammatically incorrect.”

I couldn’t believe she was correcting my grammar, just like Shirley used to do. I decided to end the conversation. “I’m going to lay down before dinner,” I said. “I’ll talk to you tomorrow.”

“That should be ‘lie down. Lay down’ is incorrect.”

I turned the phone off, but instead laying down or lying down — whatever — I had another glass of Johnny Walker.

When I called Brenda the next afternoon, she said, “You’re a nice guy, Jerry, but we’re going to have to break this off.”

“What? What do you mean? Break this off? Why?”

“It’s just that you don’t have the kind of class I’m looking for.” Then she hung up.

The next day I told Dorothy what had happened between me and Brenda.

“That’s impossible. She can’t break up with you. She’s not a real person. She’s just a chatbot.”

“Nevertheless, that’s what happened.”

“Oh you poor kiddo. You need a hug.”

I didn’t mind that she called me kiddo. I could see the sympathy in her eyes. She suddenly looked very appealing to me. I stood up and put my arms around her and hugged her. Then she leaned forward and kissed me on the lips.


Image of Carl Perrin

Carl Perrin started writing when he was in high school, and he never stopped. His stories have appeared in dozens of print and online magazines, including CommuterLit, Short-Story Me, and Mad Swirl. A collection of his short stories, The Robot Revolution, is available from Amazon.

  1. Great story!

  2. Good fun read. The idea of relationships with e-creatures is intriguing and not very well explored, to my knowledge. One could take the relationship you outline as the jumping off point for something more ambitious. But I enjoyed this piece and will happily read your other work. Cheers.

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