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The Time-Traveling Wingman

The Time-Traveling Wingman
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If you could give your younger self some relationship and sex advice ... what might have changed?

  Scene One: His First Lover

sexy teacherHe is 22, in college, some months after returning from a year in Africa where he met his first true lover—a woman who adored him perhaps more than he knew how to comprehend. She was beautiful, exotic, and devoted. She was experienced—six years older—and insatiable. For a year, they were perfect together.

She is visiting. She wants to move to the United States and live with him while he finishes college, and then perhaps marry.

He says: “Move. But I am not ready for … any of the rest of that.”

She says: “I would move for you, not otherwise. I will never see you again, and I will hate you.”

He says, helplessly: “Don’t hate me. Maybe in a few years, I’ll be ready …” He does not tell her: “You were my first. I cannot imagine that you will be my only, my last.”

But he thinks it.


What do I tell my younger self, about that? She left, of course. She did not come back. She did not write. She disappeared. In time I realized how extraordinary then was, how dumb lucky I had been, that she wanted me.

For 25 years, I wondered if she hated. For five years, thanks to the Internet, I have known she did, and then she didn’t. But then I made her angry again. “We can start again,” she said. “We can’t,” I said, meaning I couldn’t.

Back in time, I touch my 22-year-old self on the shoulder. He looks at me. I shake my head and say nothing. I cannot change this. I wonder what my 70-something self will say to my 50-something self.

  Scene Two: The College Professor

sexy teacherHe is 23, sitting across the restaurant table from his college English professor, a woman who looks to be perhaps 40 … though what does he know? She is old, to him. He overslept one morning and missed the final exam. Because she “loved a paper he wrote” for the class, she said, she offered him an oral makeup exam, over lunch. Though he has read Penthouse Forum for years, it does not occur to him until the second pitcher of Sangria is served that he is, in fact, in the middle of a Penthouse Forum story.

He freaks out a little. Later, he does not remember what he said, exactly, but he leaves the restaurant alone. He waits for his grades. He gets an “A” in the English course.

At 50-something, I have of course heard that it is wrong for professors to sleep with students. However, as time-traveling wingman to my 20-something self, I have this to say in that restaurant back in 1979: “Drink the Sangria. Go home with her. Fuck her. Do whatever she wants. Tell no one. If you don’t, you’ll always wonder.

Because I always have. Wondered, that is. There are some mistakes that I regret not making.

  Scene Three: Drinks are Involved

The year is 1981. Or was it 1984? Or 1980. Whatever. He is in a bar. Or at a college party, though he is no longer in college. Where else would he meet women? There are adventures. There is the time he is asked to leave—fast—after the second night of what should have been a one-night stand because her boyfriend was on his way home, which was okay, except that they’d gotten to her place in her car, and hitchhiking back to Boston in the snow had not been his plan.

There is the incident with the girl who said she was a Yale sophomore, and turned out to be a high school junior and the daughter of his former professor. And once, there is waking up in a coatroom of a women’s dormitory with his pants around his ankles and a broken condom on his penis, and he remembers the girl vaguely, but not at all how he got, well, here.


There was more than that, of course, quite a lot more. And at 50 … it is good to have stories, the kinds of stories you tell a new lover who wants to know what you were like back then, and she wants you to have been bad, some, because perhaps she was.

Have a beer-St. Pauli GirlWhat would I tell that boy? Every story is different and a keepsake, yet there is one thing I want to tell him still, one thing I want to say just to see if he would listen. It is something that the kid’s wingman should have said, but my 20-something self never had one, really. There is just me, his 50-something time-traveling self. “Easy on the booze, Pal,” I would have said, because for almost every story worth telling, there was too much drink involved. He does not know that those drinks will gain on him, ride him down.

Would he listen to me? I don’t know. He didn’t listen to anyone else, about that. I would have to try, though. I think of the old joke: “You can tell a 20-something, but you cannot tell him much.”

As time-traveling wingman to your younger self, you do not have a lot of power. With my older self’s advice, what would have been different in my 20s? There would have been a few less drinks, perhaps; a wild night with a professor, maybe. I would have always carried condoms in my wallet, just in case. I might have appreciated, sooner, that every woman’s body was different; that all nerves, in the end, connect to the brain; and that talking about sex can be as much fun as having it.

On the other hand, my 20-something self might not have listened even on the little things. That’s okay. He has time to learn.

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