When asked to share my most embarrassing moment, I have a variety of options to choose from. There was the time I stalled a brand-new Mazda Miata five times in front of a half-dozen used car salesmen, and there was another time when John Stockton asked me if I was a girl.
But the winner took place inside a maroon 1983 Honda Accord back when I was still in high school. I was on a date with a girl I had known for a little over a year. We'd been out a handful of times, including a couple of school dances, and I'd decided it was time to "make a move." This decision stemmed from the fact that one of my best friends had just taken her to Prom, and another best friend had just spent a week kissing her on stage in the school play.
We were parked at the Redwood Drive-In out in West Valley, because if seventeen years of pop culture had taught me anything at that point, it was that drive-ins were built for romance. I had pre-determined that at the most romantic point of the film, I would put my arm around my date, thus communicating my "hey baby, I'm yo man" intentions. This seemed like an airtight plan, save for two problems:
1. We were watching "Grumpy Old Men."
2. My car had headrests.
I was able to overcome problem #1 by waiting until the fish and tackle shop owner played by Ozzie Smith died. It was as sensitive a moment as I was going to get, so I took it. I casually stretched out my right arm and tried to drop it behind my date's head. But she was leaning back against the headrest, so instead my arm wound up jammed in the gap between the top of her head and the top of the headrest. It was like my arm was one of those striped tollbooth arms and she was a car that tried to pull out of the parking lot without paying.
Slowly, with my arm still propped up on top of her golden-haired head, she turned and stared at me with a look of confusion that justified any fear I ever had about making a move on someone of the opposite sex.
I tried to address the situation with a non-verbal gesture, meaning I started pushing down with my right arm to try to force it behind her head. Another half-second of confused awkwardness followed, then when my date finally realized what on earth I was trying to do and leaned forward a bit, my arm fell over her shoulders. Then we sat there silently for another forty minutes while Jack Lemmon and Walter Matthau worked out their differences--I can't remember which of them wound up with Ann-Margaret--and I took her home. Or maybe we stopped at Village Inn. The other details are a little hazy.
While we remained friends, we never went on another date. After I returned from Chicago a few years later, a mutual friend told me she married a guy she'd met on a blind date*. I don't know if she ever told anyone about my mishap at the drive-in. My guess is no, since compared to the horror stories I usually hear from my female friends whenever we get around to comparing dating notes**, my little mishap comes across as utterly harmless.
I do remember seeing her at our 10-year-reunion, but I can't remember if I talked to her or just kept an awkward distance. Once a girl I've dated gets married, even if we are on good terms, I don't go out of my way to stay in touch. I'm pretty much content to fade into their personal history as one of those "other" guys they met along the way.
The day after that date I took the headrests off my car, and they stayed off for eighteen months until I left on my mission. Never let it be said that I don't learn from my mistakes.
*Reason #34 I hate blind dates.
**Reason #18 I am grateful to be a man.