Ch. 10: My First Times All Have One Thing in Common

From crushes to kisses to you know what.

There are few things more memorable to a person than the various first romantic encounters they have life. Mine all have one thing in common. No doubt you may already know what it is.

My First Crush (IRL)

The first girl I ever remember having a crush on (in real life) was Jennifer in the second grade. (Yes, that was her real name. The fact that I remember it so many decades later just illustrates the impact it had.)

She was a brown-haired little girl with dimples and ruby red lips. It was a small private elementary school in Southern California. My class was located down the hall from the bathroom. Halfway down the hall was Jennifer’s class.

Whenever I’d go to the bathroom, I’d have to pass her class. She’d get up from her seat, then blow me a kiss right before I got to the bathroom. I reacted the way any boy that age would. I’d wipe the air kiss from off my cheek, exclaim “Ewww! Blech!” Then slam the bathroom door behind me.

“Gross!” I would think to myself.

But I started to notice that I was going to the bathroom a lot in the second grade that year.

“Mrs. Crabtree, may I go to the bathroom?” (For the record, I don’t think my teacher’s name was Mrs. Crabtree. So if you’re gonna make one up, Spanky and Alfafa’s teacher seems as good as any.)

“Again Ronny? You’ve been twice already.”

“I know, but I really gotta go.”

“Very well. But hurry back.”

I’d then take a leisurely stroll down the hall, slowing down just as I approached Jennifer’s class. As I passed the door, I’d casually look over my shoulder towards her desk. Adjusting the length of my gate so as not to pass the door too quickly. But still walking fast enough so it wouldn’t look like I was lolly-gagging around. (In Star Wars parlance, this would be known as “flying casual.”)

As soon as she saw me, I’d feign panic, then run to the end of the hall and wait patiently for her to come to the class doorway, turn the corner, and blow me a kiss.

“Ewww! Blech!” Wipe face. Slam door. Then sit on closed toilet seat smiling ear to ear.

My First Kiss

My first kiss came relatively late in life. I was a senior in high school at a YMCA retreat held at an abandoned army base in San Luis Obispo, CA. I was hanging out alone in my cabin with Helen (not her real name). Helen and I were flirtatious friends all semester. She had a cute blonde bob haircut and bright smile.

For some reason I don’t recall, we had been at odds for a number of weeks, and this evening we were talking it out. One thing led to another and kissing ensued. Things actually got a little more heated than I had expected. I think we were both surprised by how far we went. It wasn’t “all the way,” as they say, but it was far enough.

Shortly after as I walked her back to her cabin, I got another first — my first lesson on what NOT to say to a woman after an intimate encounter.

Making a reference to the fact that we had been at odds for a while, I said to her, “So, are we better friends now?”

I could see the pain and disappointment in her eyes after those words left my lips.

“Better friends?” She exclaimed.

I could tell by the tone in her voice and the emphasis on the word “friends,” she was probably thinking we were way more than just “friends.”

She was visibly upset and wanted to walk the rest of the way back by herself. Confused, I said “okay.” (Lesson #2: When a woman whose heart you just broke says she wants to walk back to her place at night in the dark, you accompany her, even if it’s an awkward, silent, stroll that seems to last forever).

More than 25 years later I would learn in a counseling session that I have what’s called a low E.Q., or emotional quotient. It’s not like autism or anything. It’s just that sometimes I don’t pick up on emotional cues that people give; or I’m totally oblivious to how certain things I say may emotionally land on people. There was no clearer example of this than that evening when I told a starry-eyed sophomore, hopelessly infatuated with a clueless senior, that after such an intimate encounter, all she was to me was just a “friend.”

Later that night, I had a pie thrown in my face by Helen’s best friend. Me. The nice guy that everybody liked. I felt mortally guilty after that. I tend to feel guilty pretty easily. (This quality will play a role in our story later.)

My First, well, You Know

I was 19 and she was 29. We met at a dance club in L.A. during my winter break. We had spent quite a few days together just hanging out. She was a great kisser! (In college, I made up for a lot of lost kissing time I didn’t get in high school.)

She was also the first time I ever got a case of blue balls. We spent an entire day hanging out and holding hands. She wore a loose blouse and tight, denim “Daisy Duke” shorts. All day long I kept thinking exactly what you’d think a 19-year-old heterosexual boy would be thinking hanging out with a hot 29-year-old MILF (yes, she was a single mom of two. Or was it three? I forget. And frankly, didn’t care.)

Nothing happened that evening because she said she had the Clap (or something like that). In retrospect, it was probably sweet of her to show restraint. (Although, it was kinda messed up to dress like that and be rubbin’ up against me all day. WTF!)

The big night it happened in a car in front of my cousin’s house after going to a dance club together. As we made out in the car, she gave me that look. You know the one. The one a cougar gets right before pouncing on its prey.

I was the prey. She pounced. (Cue fireworks!)

That’s pretty much all the details I want to share about that (use your imagination for the rest).

Oh, dear! I hope my aunt isn’t reading this. She’s a nice Christian lady who would not be too fond of the fact that I lost my virginity in a car in front of her house).

Anyway, yes, she was white. (The person I lost my virginity to. Not my aunt. Just to be clear.)

My First Girlfriend

The first serious girlfriend I ever had was in my junior year at Cal Berkeley. You guessed it. White.

Little did I know that this string of pale-skinned love interests would come back to haunt me in a way I could never imagine. If you thought my encounter with a “spirit animal” Sam Jackson was weird, you ain’t seen nothin’ yet.

Tune in this next week Tuesday-ish for Chapter 11, and perhaps the most challenging chapter of the entire book. You won’t want to miss it! (Email subscribers will get early access).

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