A Little Diddy About Jack And Diane…

man and woman shaking hands

*Cues up John Cougar*


A tragi-comedy in three acts:

Act One

Jack – “Hey Hotstuff!”

Diane – “Lol”

Act Two

Jack – “Hey Hotstuff!”

Diane – “I’ma married woman! Harassment!”

Act Three

Jack – “Muh feelz!”


Jack is a guy I met around a year ago. He’s a good guy, a nice guy. If I had to guess, I would say that he’s in his early 50’s. Maybe 51 or 52. He’s a hard worker, good with his kids, in good physical shape, and he’s divorced. He’s also blue-pilled pretty bad.

Jack calls on me from time to time, just to catch up, shoot the shit, and talk guy stuff. When it comes to women, Jack doesn’t really understand them or their nature, and that’s okay for Jack. Any time he wants to get serious with me, he brings over a twelve pack of my favorite beer.

The other day he called and asked me if he could come over for a bit and I told him sure. He showed up about an hour later with a twelve pack in hand and I could see the fire that engulfed him from the street. Imagine a six foot man standing at your door, completely engulfed in flames, smiling, and holding a twelve pack of beer, and that would be Jack.

I invite him in, the cat’s caught scent of the fire that enveloped him, and they headed for greener pastures. My cat’s ain’t nobody’s fools. They know a man who is burning when they see one. I wondered briefly if his flames would singe my carpet, but by then it was too late. He was already half way up the stairs.

We sat on the couch and he handed me the twelve pack. I couldn’t wait to get my hands on that first beer. There’s nothing quite like that first taste of an ice cold beer after a long day, and I looked forward to it. I pulled a bottle out of the box, twisted off the cap, and took that first long pull. Yep, that’s it. That’s the stuff.

I must have been enjoying the beer so much because I totally missed what Jack was telling me.

“Come again?” I said.

“I said, I’m in a bind. I don’t know what to do. I got sideways with my boss, and now I think I’m in deep shit.” Jack replied.

“What happened?” I asked.

“I think Diane is gunning for me. I think she wants to fire me.” Jack said.

Now here’s where it gets interesting. Jack has been working at his current job for under a year. He’s a fairly new employee. It just so happens that I know his boss, Diane. Well I know of her. She ran in the same circles as my ex-girlfriend did. That’s how I first got to know Diane. From what I remember of her, she seemed pretty decent. She has been at her company for a few years, worked her way into management, and from what I remember her telling me, she cares about her subordinates very much. I didn’t take her for someone with an axe to grind or someone that is a power tripper.

I need to back up for just a moment.

A couple of months ago, Jack and I had a conversation over the phone. I remember him telling me how much he liked his job, and how everybody was really friendly, almost like they were friends. I also remember Jack telling me that when he would talk to Diane, he would walk into her office at the end of his day, and he would say something like, “Hey hotstuff! How’s it going?” Or “Hey good lookin’, what’s cookin’?” According to Jack, she would laugh and smile, and then they would discuss whatever it was that they needed to discuss. I remember telling Jack, that you’re co-worker’s aren’t your friends, and that it probably wasn’t a good idea to be addressing Diane, his boss, with those terms of affection. You never know how someone will take it.

Apparently Diane wasn’t too keen on Jack calling her “hotstuff.”

He found that out a few days before he got a hold of me when he was called into the big bosses office. Diane and the big boss were there waiting for him. From what Jack told me, Diane felt that his remarks were inappropriate and it made her uncomfortable. I believe the term “sexual harassment” was mentioned. Diane mentioned other things like “being a married woman” as well.

Obviously Jack ignored my warning and my advice, and here he was, facing the music. Needless to say, Jack was completely caught off guard with the turn of events. He apologized profusely to both bosses and explained that it was a big misunderstanding. He wasn’t trying to hit on her, it was a line or something from some movie that he had watched and had liked. He really meant no harm. He thought everybody was friends and that bantering around like that was something that friends did.

Apparently the big boss was satisfied with Jack’s answer and explanation. I guess he saw it as a big misunderstanding too. Supposedly Diane was good with it as well. Everything could go back to normal.

I asked Jack, “Was there any punitive action taken against you? Were you written up or suspended? Any “sensitivity training” or sexual harassment training? Anything like that?”

“No, not at all.”

“So what’s the problem then?”

The problem is, Jack got his feelings hurt. He’s pissed off. I get it. I totally understand it. I’ve been there, years ago. Jack is uncertain of his future with his job, he’s not sure where he stands, and he’s paranoid. He’s paranoid that Diane actually isn’t okay with things. But here’s the thing, remember how I mentioned that I know Diane? Yeah, she’s not the type to carry a grudge. I’m not one hundred percent certain on this, but I’m more than reasonably certain, that she isn’t “out to get” Jack.

Jack isn’t making things better. He’s the type of guy that thinks of things in very binary terms. Everything is either black or white with him, so when he wants to “just keep it professional,” that’s what he does. You ask a question, bam, you get an answer. Bang, trapdoor shut.

He mentioned that Diane has tried a couple of times since the meeting to engage him in conversation. He told me he wants to “keep it professional” now. Diane asks him, “How’s your day?” Jack replies with, “It’s fine,” turns his back on her and walks away. Diane mentions doing stuff with her husband and kids and asks Jack what he’s doing for the weekend, Jack replies with, “Let’s just keep it professional, I don’t want to talk about it.” Then he shuts his mouth. One of Jack’s problems is that he’s wanting to deal with Diane as if she was a man. He wants to logic his way out of this. It doesn’t work like that though. Not with most women. One of Jack’s biggest mistakes is that he assumes that she thinks like he does. I tried to get him to see otherwise.

I mentioned to Jack that it didn’t sound to me like Diane was “out to get him.” If anything, it sounded more to me like she was trying to make a peace offering with him. She was holding out an olive branch. From what I remember about Diane, she likes harmony, she’s a nurturer. If Diane was angry or repulsed by what had happened, I would imagine that instead of trying to engage Jack, she would try to keep her distance from him and would most likely be very cold to him.

Jack didn’t want to hear that though. Apparently he would rather be a martyr. A martyr for his feelings. That’s why he’s on fire. That’s why he gets to burn.

I told Jack, “Hey man, fuck your feelings. Nobody gives a shit about martyrs. You’re worried that Diane is gunning for you? I don’t think she is, but if you keep doing that butthurt thing that you’re doing, she is going to come after you eventually, and it’ll probably be for insubordination. You have to let that shit go. Don’t do it to kiss Diane’s ass, or grovel to keep your job, but do it so that you can enjoy getting back to work and doing your job. You keep doing this cold, “keeping it professional” thing that you’ve got going on and you’ll create your own self-fulfilling prophecy.”

Jack said, “Maybe one day, but not today.”

I replied, “Sooner or later you need to let it go and get back to being friendly, but not necessarily friends. Better sooner than later though.”

After that, Jack thanked me for my time, I thanked him for the beer, which I had drank a few of them by that time, and I saw him out. I last saw him climb into his car and drive away. Nothing like watching smoke billowing out of a car window and a man on fire driving.

Maybe he’ll take my advice, maybe not. Either way, I got free beer out of it and Jack gets to burn.

“A little diddy ’bout Jack and Diane, two American kids bein’ cogs in corporate-land…”

*Fade John Cougar*

Sharpen Your Mind. Weaponize It. Start here and here. Sign up for my newsletter.

3 thoughts on “A Little Diddy About Jack And Diane…

Leave a Reply

Please log in using one of these methods to post your comment:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s