Our 1st Date was very telling. It was about an hour-long dinner at The Juicy Crab... To begin with she’s a half hour late, walks in with her expensive (I’m lookin-old-as-fuc) Gucci glasses and im immediately unimpressed. I can’t imagine sex between us. She looked more like Deniro from Casino than the young pictures posted on her Facebook page. And so I found myself already sold into this dinner out, and yet fighting my better judgement to “make” or “force” some kind of potential with this woman... some kind of progress. I’m even forcing myself to enjoy what I see, and to ignore the certain red flags... no, there wasn’t a lot of make up. But while that played well on my mind, it was offset by what came from her mouth. She was already making excuses for why other dates didn’t work, and why one particular date told her to her face that she was “bougie” and “a bitch.” Before dinner came I found myself apologizing on his behalf, even if she was bourgeois or saditty, with the high maintenance ways, I didn’t feel she deserved that.

After all, many of these sorts of “women of the world” are raised by Jack & Jill, they are sheltered by their parents or even by their high society relationships. But even that wasn’t the case here, as I learned later, this one had been put thru the years of the dice-roll; the groupie-sex that rappers authored, followed by dopeboy girlfriend sex, which she explained to me as occasional “risky sex and random backseat experiences.”

So this is who I had sitting in front of me, across the table of crab legs. We’ll call her Cheryl. 

So I’m already clear that she’s aging like a bottle of hard liquor. She’s already outside of my preferred window of that sexy, mature 30-something. But there’s no doubt Cheryl is “seasoned” but also still (as notes in her Facebook plea) wants for random travel adventures and sexual thrills. “Not everyday, but random.” As for me, I’m shrugging my shoulders with the pregnant pause. “Okay.”

Okay, so blame me for how I got here to the table. This newfound freedom I have, The veteran entrepreneur, complete with multiple revenue streams and how I just don’t give a shit. #nofilter

So I turn my phone down and pay attention as she drags me thru her dating woes. But thru the smoke and mirrors of her conversation, I’m asking myself “fella, what is attracting you to this woman? What can you attach to that will force this in a positive direction?”

 

STRIKE ONE: "DINNER WITH SAM ROTHSTEIN"

SHE SAYS: “Waiter, since my meal isn’t right would you mind sending a couple sausages over?”

To myself: ‘Jeez, she’s into swine.’

So she proceeds to explain to me that “everyone dies from some health issue” and that she’s avoiding the one that runs in her family. When I suggest changing her diet she’s already making excuses why it’s “ok” for her to eat what she wants.

Thru dinner I’m aware that she’s sneaking peaks at me, sizing me up...  outside of the restaurant I lied and told her “I enjoyed myself.” 

And again I could see her leaning into the conversation, no pulling away. Not leaving room for mystery or the chase. Something told me she was easy. At that moment I took a leap of faith and (random as I like to be), I scooped her off of her feet to see what she weighed in my arms. That isn’t something new, but something I’ve done on occasion. This also creates a closer bond as my hands are on her body and her arms/by default fall around my neck. Creepy, yes. But not if I don’t reveal these truths? 

STRIKE TWO: "EASY LIKE SUNDAY EVENING"

So yes: At the end of the first date I said “let’s do this again” to which she said “I hope so.” and I thought “Damn sisters gotta do better.” She was supposed to say “we’ll see.” She was supposed to shrug and say “I’ll think about it.” She could’ve even patted me on the shoulder and winked and she’d have nailed me down... she woulda had me wonderin “wtf is SHE packin’ between those thighs!?” But no. Instead I’m an instant visitor to her private sanctuary. Her home. I wanna say: Who does that? And “She’s that easy?” But then, I know me. And I know I’m the “great expectation.” You realize this after so many experiences where I’m not forced to try hard or to go thru hurdles. Just take me to the velvet rope. 

So anyway, DATE ONE she was already beggin for it, kept lookin up at me with her puppydog eyes. Shit, i’m thinkin... wondering, do most women 50 and older have puppydog eyes? And BTW, it was 3/4 times that she mentioned “I’m about to be an ‘empty-nester’ and also that “my son is away until Wednesday...” so she clearly wanted somethin to go down between date one and Wednesday. Sex perhaps? Companionship? 

THE SECOND DATE is suddenly the next day. It evolved from a series of text messages on Saturday and at least one phone call. I also recall her saying on three occasions that her grown son was away for a few days. I couldn’t tell if that was her way of saying “the house is all mine come and take me.” Or maybe there was some other platonic activity she had in mind. Would we be kissing? Would we be cuddling? Shit, even that would be a new thing since 54yr old lips hadn’t kisses anything over 35... well, in nearly a decade.

35... Hmmm. My consumer conscience is  calculating things...

So far, the Juicy Crab dinner (heavily discounted because she pushed the envelop on the order being wrong/added hard boiled eggs) and then add a bag of shrimp I brought over to her 1st floor, “300k box” she called it, and my total bill for interacting with this woman cost all of $35.

 

STRIKE THREE "MUTT HAIR, HER HAIR ALL IN THE AIR"

Lol. And nope, you ain’t miss nothin; (the day after) she did invite me up to her place. Already I knew she was thirsty and her signals were saying “please accept me.” And would I have gone down the rabbit hole for the sex? Well for a man that’s always talkin about discilpin' Uuuh likely not. Nevertheless, I made sure I “balanced” my mind and body before the date at her place. So the only “desire” I had was for the Jumbo shrimp I cooked for us. Yep, she got a chance to catch these skills, and I figured that would be as far as it would go if this alignment wasn’t in synch. I had a few discussions before the date, looking for people to maybe talk me out of this new web I was about to bounce on. She had webs too, bragging about her former rapper husband and how “his money is always on time” and inevitably how she rolled the dice many late nights with this and that cheatin dope boy... and I already drew lines in the sand about how rapper groupies are pushed to the limits if only to satiate these egos. Shit I know this more than most because I wrote the damn book “Rappers R In Danger!”

So yeah, I was already “on alert” but then this annoying lil mutt bouncin all over the place, on and off the couch where we sat. Loved dogs for my entire childhood. But this critter was giving me the creeps, not because he was so filled with zest, but that he was so close to my food/just unsanitary circumstances in an otherwise clean environment. Annoying, creepy and I felt like crabs were crawling up my arms. She even grabs the pup from time to time to stroke it, and then she’d coincidentally stroke her hair.

During dinner she stashes her dog in a small cage nearby and he continues to make dizzying circles like a hamster on the run. 

I tried to put some positive programming on the TV so that we wouldn’t get stuck into any program, so that we would get to talk to one another, but that didn’t work. She asked if I minded her releasing the dog once I finished eating and I shrugged. Of course that just turned his energy up 10 notches and again he was all over the couch in her arms in her hair and I had had enough.

I don’t know what triggered the next few minutes but she went on about how her dog was part of the family, as if it were her son, and that she slept with the dog. Then she ranted about "Well, my post said 'I have all my paperwork, current" And My response to her was Cold: Number one, "Why would I need any paperwork? What makes you think I'm ever fucking you?" and then, with my eyes on her front door “well I hope your dog can give you the orgasms you’re looking for“

I slip my sneakers on grabbed my cell phone and I couldn’t wait to get back to life as usual. A $35 lesson is all this turned out to be. Sure, I might have had her live out her remaining 50-yr old “80s groupie fantasies” on my unused dick, but considering how that was such a mental uphill climb for me, I left that house relieved, with my foot on the accelerator.  I couldn’t help thinking that failed date she experienced was onto something! But even that thought was brushed away by the wind of i-285. I cut on my Pandora. And Just focused on my agenda moving forward. A few hours of lost time to make up for. Stick to the script. Okay Nipsey...

“Legendary self-made progress, last time that I checked ... First get the money, then respect... 

Then the power, and the hoes come next”

In that order