Gentleman or Not… Here I Stay #9: The Dating Chronicles

In my guest posts here I’ve written several times about seeking out a Bro Date. I haven’t yet discussed dates with women, but I’ve had a few of those in my time.

twizzler bro Gentleman or Not... Here I Stay #9: The Dating Chronicles

Not the way to do it, bro.

My first date was in 7th grade– the same age I teach now. We saw Beetlejuice in the theater and used a Twizzler the same way Lady and the Tramp did a strand of spaghetti. That was as smooth as I could get back then– alright, it never got much better.

I had one more girlfriend in 8th grade and then bypassed dating through the rest of high school. When the same hot cheerleader wrote her number in my yearbook two years in a row, obviously that meant she wasn’t interested in me. That’s how much common sense I had about girls. My best friend and I were quite sexually mature at that age. He would grab girls’ butts in the Lazy River at White Water, then play it off when they looked back. I greatly admired his ballsiness. Once we had jobs and could drive, we dined at Hooters every chance we got.

It took graduating high school to get myself a real girlfriend. She was Vietnamese, short, and wore entirely too much makeup. Oh, and she was 17 Maury Povich 300x225 Gentleman or Not... Here I Stay #9: The Dating Chroniclesand had a baby of dubious origin– from what I eventually learned of her, she would’ve had to go on Maury Povich to figure out that baby’s daddy. But that wasn’t enough of a red light for me. I still took her on a high-class date to a local state park, where I found a secluded parking spot. There, under the shade of Georgia pines, I lost my virginity in the back of my dad’s 1988 Custom Cruiser station wagon. You might have a swagger wagon, but I had a shaggin’ wagon.

Oh, did I mention that she showed me some implants in her arm that meant we didn’t need protection? Yeah, why would I have thought twice about STD’s in the early 90s? Anyhow… ahh, to be 18 again, when you can go five times a day, even if they all add up to less than 10 minutes. When you try to find dark, remote places to park… or the parking lot of the Target where you work after closing… or a $39/night a hotel. Of course, we couldn’t actually spend the night there, as we both had to return to our respective parents’ houses. So, after showering off the bedbugs, it was always my duty to drive back to the hotel in the morning to return the key.

dying 300x298 Gentleman or Not... Here I Stay #9: The Dating ChroniclesIt was all fun and games until one night when a cop tapped on my window. Most people who joke about “being caught with their pants down” haven’t actually lived it. Later, she said she was dying of a brain tumor. Then she died in my arms. Or so she said– said death lasted about two seconds. Then she went to have outpatient brain surgery which magically cured it. They didn’t even have to cut her hair! Lasers, she said.

Suffice to say that relationship ended soon enough, as even someone as naïve as my 18-year-old self can only drink so much crazy sauce. Turns out she was an epitome of sanity and honesty compared to the girl I would first propose marriage to, but I’ll save that for the next installment.

banner manly Gentleman or Not... Here I Stay #9: The Dating Chronicles

Never let the truth get in the way of a good story… 



Gentleman or Not… Here I Stay #9: The Dating Chronicles — 46 Comments

  1. I made out so much in cars that I still get a little excited whenever I see a Honda Civic hatchback in a parking lot.

    You should flesh out that story about the girlfriend you lost your virginity to–sounds like you have some good material there.

  2. I had similar dating experiences in high school, in that I never dated. Years later, girls would confess, “Oh, I had such a crush on you”, as if it did me any good then. I still didn’t take that as a sign that they may have wanted me. And that is why I have 47 cats.

  3. Would you believe me if I tell you that I’ve never done it in a car?
    I mean, I have touched every corner of someone’s body on the back seat of a Lincoln, but never done it, done it. I grew up in NYC and had no car to drive :/
    The Vietnamese girlfriend reminded me of this:

  4. I got caught once with the Coppers,,i’m pretty sure after they saw how well I was performing orally they secretly thru the guy a eyebrow “high five” just sayin….
    Absolute worse place to get caught,,,,in the parent’s living room with “pants off” by dad!

  5. My first boyfriend was climbing up to my window at night. This was very romantic while we were dating, once I dumped him it just got creepy. One night I was at a party and my father slept in my room. He caught him in the act, the guy got scared and fell and I never saw him again:))))

Oh you know you want to give verbal ejaculation a try. Spit it out!