Entry Nine: Big Dick Energy, Small Dick Results: The Disastrous Shit-Show of Dating in Your 40s
You ever reach a point in life where dating feels less like a romantic adventure and more like an endurance sport you didn’t train for?
Welcome to dating after 40 – where everyone’s flexing Big Dick Energy, but somehow, when the pants (and the emotional walls) come down, you’re met with… well, more of a “slightly enthusiastic gherkin” situation.
And I’m not just talking about dick size (though, honestly, let’s be real – that’s part of it).
I’m talking about inflated ego, shriveled communication skills, the men who talk a big game, like they’re gonna rearrange your guts and unlock your third eye – only to show up acting like two pumps and a prayer is a personality trait.
Congratulations, sir. You are the human equivalent of a wet fucking fart.
Disgusting? Yes! Surprised? Not in the slightest.
At 40 years old, I never really dated. I was always in long-term relationships that dragged on longer than my will to live through another first date.
I found myself on Match. eHarmony. Hinge. The usual digital dumpsters of hope and heartbreak. I rolled the dice. Threw on some mascara that won’t run down my face mid BJ, burned a smudge stick, and prayed to my spiritual gods and goddesses for great dick and better conversations.
And what did I get?
Nicknames.
A full roster of dude whose real names I either forgot or blocked for my own mental safety….
Dr. Africa, Minnie Ear Mike, Yellow Beemer Bran, Muscles, Chew-Chew, Dr. Hank, Poker Player Mike, Private Plane Bret… let’s just say the list goes on.
Just to be clear, I didn’t go on dates with all these men. These were some of the men that slid into my dm’s and wasted ALL of my time.
I don’t know how to date. I was never taught how to spot RED FLAGS, I was too busy collecting like bright beautiful carnival prizes.
Despite growing up in a loving home with parents still madly in love, I somehow still craved validation from emotionally stunted men who thought a slap on the clit counted as foreplay.
One of the men I did happen to go on a date with should’ve left half-way through the meal.
Our conversation was going great. He was charming. A little short. But sweet. We vibed. We talked travel, places I dreamed to visit and want to tour.
I described traveling all around Europe. Visiting the Amalfi coast. Sightseeing the castles of England, Ireland, Scotland!
Sipping on wine in the French countryside where Madame Clicquot blended rosé champagne and became the first to popularize the blend.
Visit the Louvre and sets eyes on the larger than life –in my imagination– Mona Lisa, and feel the disappointment sink in when I realize it’s true size is a lot smaller than my mind depicts.
I then dropped a dear travel goal—visiting Germany. I went off about how much I love studying WWII history and how fascinated I am by that time period. I explained to him I wanted to see the concentration camps, walk the beaches of Normandy, and just do all the things—take it all in, every gut-wrenching, historically significant part of it.
Only to remember, a little too-fucking-late—that the man is Jewish.
Your girl basically said, “Let’s tour the ancestral trauma of your people for funsies.”
He stared at me, deadpan: “I will NEVER step foot in Germany.”
And I? Faded into the fucking upholstery.
Shockingly, he still took me out again. Invited me to his mansion in Colts Neck, let me drive his Range Rover, and paid for pretty much everything. And yet, despite all the shiny perks, I knew deep down it was never going to work. He was an alcoholic and not even remotely emotionally available.
He looked great on paper and empty in person.
I didn’t beg. I didn’t chase. I let him wine and dine me. And when he started to drift? I did the same, protecting myself from the beginning.
There’s sometimes a “Wow” factor when you can start to feel the shift.
Like, you finally got my attention — pulled me in, made me think, “Hmm, maybe this one’s different…” — just to fumble me, telling me you “over committed.”
Listen, if you just wanted to fuck—all you had to do was say so buddy. I would’ve treated you like the overpriced piece of meat I only kinda wanted. Devoured you with minimal effort, and left your ego in a to-go box on the nightstand.
No emotional investment. No expectation. Just vibes, orgasms-for-her, and a Uber XL ride home.
I fought tooth and nail to be seen — craving connection from men who weren’t capable of offering anything beyond the length of their appendage.
I stayed far too long in places I had emotionally evacuated years earlier, thinking if I just gave more, tried harder, made myself smaller, sweeter, sexier, they’d eventually show up fully.
Spoiler alert: they NEVER did. So I protect myself. Always hoping and wishing for the best. But keeping tuned-in with what my gut is always trying to tell me.
Other than, to stop eating ice cream.
When I fall in love, or genuine like, I tend to go all in. I want someone who keeps showing up just as much as I do. Who keeps doing the little things. If you opened the car door when you were trying to get my attention, keep fucking doing it after you’ve saw what the gentlemanly results got you.
Which is probably a great fucking blow-job and amazing sex!
Remember that I mentioned my favorite flowers are Peonies and Sunflowers. I love a great musky perfume, and an even better cologne on my man.
Simple things… take me to a restaurant you know. Order for me because you paid attention when I said I “panic under pressure and hate wasting money on shit meals.”
We don’t have to go fancy. Grab some sandwiches, light a fat fucking joint, and let’s take a walk. Grab my hand—and ass— like you mean it, and hold it with confidence.
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Laugh with me. Make me feel safe, seen, and like our life will always be on this higher level of commitment that we never question US.
Time. Affection. Communication. Reciprocation. Vulnerability. Emotional maturity. A man who doesn’t flinch when I talk about my goals. A partner who listens when I speak and doesn’t look like he’s being held hostage by feelings.
I want to be someone’s person – their biggest cheerleader, the one they come to when shit hits the fan, when they land the job, when they need someone to pull the damn splinter out of their soul. And vice-versa.
My soft place. My hype-man. My emotional safe word.
I might be loud, sarcastic, and way too caffeinated before 7am, but I know what I want. I have goals. Visions. Drive.
I’m not dimming my light for anyone. I’m not sitting in anyone’s half-assed energy. You don’t get to mope through life and expect me to carry your spark for you.
Can we burn bright together?? If not, then we burn out.
I don’t need your money, nor do I want your manipulative compliments wrapped in emotional absenteeism. And I certainly don’t need to hear another man explain to me how he “has commitment issues” at fifty-three years old. Bro, you have more years behind you than ahead of you… what are you waiting for??
Dating in your 40s is a circus of mismatched expectations, and men who think “emotional availability” is something women make up to sell books. And I’m not here to match energy anymore–I’m here to protect my own.
(To be continue… because my dating life is a trilogy. And this was just the origin story. YIKES!)
Until next time …
