Today I’m going to eat a major helping of humble pie and tell you about the biggest screw ups I’ve ever made with women. I promised myself when writing this article that I would include the biggest, dumbest mistakes I’ve ever made even if they made me embarrassed to reveal them. I actually came up with so many that the article ran way too long, so I’ll post some now and some later in a future installment.

-By Caleb Jones

The reason I want to share this with you is to avoid the common phenomenon of “well, that might be easy for Blackdragon, but not for me” stuff that is so common when you read about men’s exploits with women online.

As I have talked about before, and as you’ll soon see, I was once just a standard beta male, doing absolutely everything wrong with women until I learned and practiced and got better. I started on this journey after being married for almost ten years, being ten years out of dating practice. (Not that I was super dating experienced before I was married either!)
These screw ups are listed in no particular order.

Too Asshole

One of the very first dates I ever had back in 2007 was with a woman in her 30s who was damn near a 10 (for a woman over 30 at least). Blonde, gorgeous, smart, fit, fun, and awesome. We met on Match.com and our first date was at a bookstore coffee shop.

We really hit it off. Her body language was fantastic and she complimented me more than once regarding how “handsome” I was. Still inexperienced, I was surprised a woman like that would actually like me, or what to do about it.

After the date, when we left building, she was standing on the sidewalk as we said goodbye and she stood there in front of me, not moving, her head tilted up, and her lips out. Clearly, she wanted to be kissed. I shrugged and gave her a nervous peck-kiss on the mouth and said goodbye. (Oh BD, you dumbass.)

Later we were having a conversation over email and I hadn’t yet pitched the second date. (Dumbass.) During this phase of my dating evolution, I was convinced that since betas never got laid (untrue), I had to go the opposite extreme and be a complete asshole. So I sent her several emails with “jerk” dialed up to ten.
She sent me back an email about how appalled she was and that she never wanted to see me again.

I could have had sex with this woman and she could have made a great MLTR.
The bottom line is that the sweet spot between beta and asshole is about 50% past the middle, towards asshole, not all the way to asshole.

Time Waster

Around this same time, I was going out on dates with a woman who was about 40 but still blonde, fit, and hot. As the typical over-33, she constantly demanded fancy dinner dates. Being the dumbass I was, I obliged. Pay for dinner, talk for hours, kiss goodnight. Pay for dinner, talk for hours, kiss goodnight. Pay for dinner, talk for hours, kiss goodnight. Yep. It’s the beta male dating model.

After about four repeats of this, my blueballs were so blue that people started asking me if I had joined the Blue Man Group. Over texts, while scheduling date number five (kill me), I told her she just needed to come over to my place. She got indignant and asked why. I told her she knew why. She said, “For sex?” I said yes. (Ugh. I’m cringing as I type this. This shit is painful to recall.)

She then gave me the standard ASD over-33 song and dance about how that was too planned and not romantic blah blah blah buy me more dinners and maybe you’ll get some blah blah blah I’m worth the wait blah blah blah and I could use a new Coach bag too blah blah blah and I’m amazing in bed blah blah blah. (By the way, this woman made a six figure income.)

We didn’t get anywhere. A few days later we had another huge, long text conversation (ugh) about having sex. I threw tons of guy-logic at her about how I had spent X amount of money on her and now it was time blah blah blah and she responded with woman logic about how on the first date I had only bought her a bottled water blah blah and then I said that I’m sure she didn’t make her last boyfriend wait five dates for sex blah blah and she said that was different because he had six pack abs blah blah blah BLAH BLAH.
This went on for….a fucking hour. I’m serious. A hour long text conversation about using logic in order to convince a woman to have sex with me.
I never saw her again.
Shut Your Damn Mouth, BD

One of the very first younger-woman encounters I had was a first, and I think second date with a very hot 20 year-old. We really hit it off but I didn’t pull the trigger. We had trouble scheduling the third date because of her schedule, but it was very clear she wanted to see me again. (She was initiating contact often, etc.) Finally, when she had some time, she said she had met someone else and was thus reluctant to see me again.

I then immediately rolled into a huge pile of massive over-verbalization about how it didn’t make any sense to commit to monogamy to any man after just one or two dates. (Holy shit.) Of course she immediately got defensive and told me to let her live her own life blah blah blah and I said she was free to do whatever she wanted but she was making a mistake blah blah blah.

She ended up insulting me and blocking my number. Never saw her again.
Don’t Make It Complicated
Was on a third date (I think) with a super-hot Korean woman with double-D boobs (yes, big-titted Asians do exist, they’re just rare). We were at a local bar having drinks, and we were both getting horny. Sensing my moment, I told her we should go back to her place (we were much closer to her place than mine). She said she couldn’t, that her daughter was there with her friends, but she still was clearly DTF.
I told her she should come back to my place, but she complained it was too far. I could have taken her back to my place if I pushed it, but I was a pussy.
Then, genius that I was, I suddenly remembered that I had recently read on a PUA forum about a guy who regularly took girls back to hotels and fucked them there. Ah ha! I could do that!
I then told her that I would get a hotel. She was very reluctant, but agreed.

So there I am, driving around town in an area I wasn’t super familiar with, with her in the passenger seat, looking very nervous. I was frantically looking around for a god damn hotel (this was before smartphones or Google Maps). Finally, I found a hotel! It was disgusting, rotting roach motel that smelled like urine, cum, weed, and cat turds. All the blood was in my cock instead of my brain, so I didn’t register any of this.

After fucking around renting a room for about 45 minutes and spending $75, I walked her up to the hotel room. She looked disgusted and terrified.
I got her on the bed, started to take her clothes off, and she was just too turned off and nervous. I ended up getting nothing.
Later, over texts, she said, “You ruined it. I just wanted to fuck in the car.”
Shut Your Damn Mouth, BD! Again!

I once had a brand-new MLTR I was very pretty pumped about. We had only had sex one time and had been sexual (blowjobs, etc.) several others. She was in her late 20s, super hot, super blonde, a Cameron Diaz lookalike, and a corporate chick. I was so excited to have her (first mistake).

I made the classic guy mistake of getting way too comfortable before Lock-In (when you have full-on sex with a new woman at least twice). Sitting in my home office, we were looking through photos on her Facebook page (ugh). As she scrolled through them, there were a few pictures of her and an overweight woman doing funny poses in a forest.

“Who’s that fat chick?” I asked casually.
Her eyes widened, darkened, and she turned to me and said angrily, “That’s my AUNT,” as if to say, “That’s my favorite relative you asshole!”
“Oh,” I said, “Cool.” Great recovery, dumbass.
That day after she left, she suddenly stopped responding to my texts. I never saw her again.
Surprise!

Once I was out on a first date with a super hot 23 year-old with long, dark hair. We were really hitting it off and I was getting excited to have sex with her. During our conversation, she made mention of the “dark stuff” she went through “two years ago.”

I finally said, “What dark stuff?”

“Well, you know,” she said.

“Know what?”

“Well, the reason I write this stuff on my profile is so I don’t have to have these awkward conversations. I mean, you read my profile, right?”

I hadn’t. I don’t read profiles. It’s not efficient. So I sputtered and said, “Uh, yeah, I read some of it.” (Oh god.)

“So,” she said carefully, “You know I was born a man?”

AAAHHHH!!!

“Uh, yeah, of course,” I lied.

“Oh good,” ‘she’ said, “I was so nervous for a minute there.”

Simply amazing. The person sitting before me whom I was getting ready to fuck was a pre-op transsexual, complete with fake boobs and a penis, and I had absolutely, 100%, no idea until she told me. She looked, sounded, and acted just like a girl. A super hot one. I was seriously amazed at the medical technology involved in the transformation.

I actually recovered pretty well. I asked ‘her’ all about her procedures and the medical aspects, which I found quite interesting. We actually had a pretty good talk. In the end, I told her to “text me,” and thank god, she never did.
I can only imagine what would have happened had we not had that conversation and I had just proceeded..

Want over 35 hours of how-to podcasts on how to improve your woman life and financial life? Want to be able to coach with me twice a month? Want access to hours of technique-based video and audio? The SMIC Program is a monthly podcast and coaching program where you get access to massive amounts of exclusive, members-only Alpha 2.0 content as soon as you sign up, and you can cancel whenever you want. Click here for the details.