On boyhood crushes and embarrassing tales


We all have embarrassing stories to tell.

Most of us, however, opt not to tell them.

I do.

In the early days of 1990, the big thing going on at Mahopac High was Illusion, our school rock band. Over a three-night span, students would fill the gymnasium and watch our peers cover songs by Styx, the B52s, Bryan Adams, etc. It was fun and cool and funky—and it resulted in my having an absolutely ginormous crush on Teresa McClure, the group’s keyboardist.

At the time, I worked as the sports editor of Chieftain, the school newspaper. Hence, I decided what we needed was a profile of McClure—a girl I didn’t know; a girl waaaaaaay out of my league. Somehow I arranged an interview, and we sat down at a table in the library. For, oh, 30 minutes, I lovingly stared into Teresa McClure’s eye, throwing out one softball question after another while thinking about what our children would one day look like. She was pretty and perky and—best of all—musical (as Kay Hanley rightly noted to me, the ultimate turn-on), and I desperately wanted her to become my girlfriend (one of which, at that point, I’d never had).

The story ran on the front page of our little paper, and I hatched a plan.

An amazing plan!

A brilliant plan!

A surefire plan!

A plan only a 17-year-old virgin could ever think of.

I looked up Theresa McClure’s phone number. I found a quiet place. I dialed it. Someone answered. I hung up. I dialed it again. Someone answered. I hung up. I dialed it again. Someone answered. I … I … I …

“Um, can I speak to Theresa?”

“May I ask who’s calling?”

“Yes, eh, Jeff eh Pearlman. From eh eh school.”

“Hold on, Jeff …”





It was the most angelic voice I’d ever heard via a telecommunication device. Sure, looking back she probably had no recollection of our meeting. But, hey, that didn’t stop me. I had The Plan. “So, Theresa, this is sort of weird, but my dad gives me money every time I get a front page article in Chieftain. So, eh, I’m calling because I sort of owe you, and I wanted to see if you’d want to go out some time?”

The words were awkward and pathetic.

“OK,” Theresa said.

OK? OK! OK!!!!!

“Great,” I said. “I’ll see you at school …”

That was that. From that moment on, Theresa McClure avoided me like herpes. I’d walk past her locker, oh, 30 times a day (stalkers learn young), and she’d never glance my way, never even look. I left her notes that went unreturned. Passed messages via mutual friends that died on the vine. Ultimately, I asked Laura Garraway—a cross country teammate who knew Theresa—to give me the truth.

“You really want it?” she asked.

“I do,” I said.

Laura gulped. “She thinks you’re … nice,” she said. “But she wants nothing to do with you.”

“By nothing, you mean …”

“Really,” Laura said. “Nothing.”

It was my first broken heart.

PS: Here’s the crazy conclusion. About seven years ago I wrote a magazine piece about all my boyhood crushes, and what ever became of the women. I tracked Theresa down, and we went apple picking together with our families. She was lovely and charming and delightful—and we’re now Facebook friends. Toward the end of our day I said, “Theresa, I have to ask—and please be honest with me—what could I have done differently?”

She smiled and chuckled warmly. “You had no chance,” she said.

3 thoughts on “On boyhood crushes and embarrassing tales”

  1. Thanks for posting this Jeff. Teresa is one of my all-time favorite people, and remembering her makes me smile. Many of us who were in her circle were CRAZY in love with her – and no one understands crazy love quite like someone in high school. As you might expect, many of us ended up in the “friend zone”, but with Teresa the friend zone was a pretty great place to be.

  2. I read this while wincing hard. Because all I could think about was my similar scheme.

    Seventh grade. Fall hard for a girl named Jamie. Never even talked to her once, just pined from afar. Built her up in my mind. Whole nine yards. Everything you would expect from a hormonal and slightly unpopular 13 year old.

    I come across a list of class phone numbers (don’t remember how) and find her phone number. I write down her number quick and stash it away. Finally screw up the courage to call.

    Jamie’s Mom: Hello?
    Me: Is Jamie there?
    JM: Yes, hang on, let me get her.
    Jamie: Hello?
    Me: Hi, Jamie. It’s George from school. I was wondering if you would want to go out with me some time?
    Jamie: No! (in a very, very, very horrified voice) and slams the phone down.

    I go lay down on my bed and mope. And then I realize…how on Earth can I possibly go to school the next day and face her. My mortification is building.

    That morning, I tell my mom that I don’t feel well and go into the bathroom and stick my finger down my throat long enough to make enough gagging sounds to convince my mom (I suspect my mom knew the truth and was sparing me the humiliation). So I stay home from school.

    Obviously, the flaw in this plan was that at some point, I had to go back to school, unless I could convincingly fake the Black Plague. So the next day, I work up the courage to go back to school.

    My middle school sent out a daily list of the students with excused absences from the day before and teachers routinely left it laying around. I scan it to make sure that my name is on it and whose name did I see? Jamie’s. She had also been absent the day before. Apparently, her mortification was equal to mine. At that point, I realized both of us wanted to pretend it never happened, my crush on her instantly dissipated and I went back to living my life.

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