This is the next installment of the book I never published regarding my history with women and the lessons I learned. If you haven’t yet, you should read parts one, two, three, four, five, six, seven, eight, nine, ten, 11, 12, 13, 14, 15 , 16, 17, and 18 before you read the article below, so you can be up to speed on where the story picks up. I’m not describing literally every woman I dated or had sex with during these times. I’m just focusing on the most noteworthy ones. Everything below is 100% true to the best of my memory, journals, and spreadsheet records, though all the names of the people described have been changed.  

We last left off about ten years ago…  

March 2010 

At the start of the month Shelly had LSNFTE’d me because I didn’t want to get married and Emma floated away, which I let her do (she’s the one who had herpes so I had no desire to keep her permanently in my life). That left me with my two solid women (and my two favorites), HBM and Charlotte. I was very happy and really liked both of them. They were both wonderful, friendly, sexual, consistent, and reliable.

The problem is that my absolute minimum number of women in my life has always been three. As I had learned before, the problem with having just two women is that it’s too close to one woman, which is monogamy, and therefore unacceptable. If you have two women, the instant one of them leaves, or gets a boyfriend, or does a LSNFTE, or you have to next one of them, then boom! You’re now down to one woman. Which is monogamy. Which I don’t do because it doesn’t create long-term happiness.

Therefore, I learned that, at least for me, the minimum safe number of women in your life is three. This way if one leaves, I still have two left and have plenty of time to go replace that third one. Even to this very day, over ten years later, I have still adhered to my Rule of Three without fail. (For example, today I have Pink Firefly plus my two consistent FBs… three women.) 

Lesson Thirty-Two

The ideal minimum number of women in your life is three. One is monogamy. Two is monogamy waiting to happen. Three is ideal.

So, I followed my standard Blackdragon system. First I went through my phone and looked through all the women I had sex with at least twice (Lock-In) and picked out a few I thought would be pleasant to see again. I sent out several “Hey! How’s it going?” texts to several of these women and waited to see which ones responded. 

Since I had only been doing this for three years, this list of women was not very large (today it’s huge). I didn’t think that statistically there would be enough ex-FBs and ex-MLTRs to guarantee that I would pull at least one or two of them back into regular rotation.  

So, I hopped back onto the dating sites, resurrected my profiles, and fired off about 200 openers across three or four different sites. I figured this plus my ex resurrection efforts would be more than enough to bring in at least one or two women. And I was right. 

This particular online dating blitz yielded two first dates. One was with a 32-year-old dark-haired Russian woman and the other was with a really cute 19year-old with extremely long brown hair (not my favorite) and a very curvy but trim body (my favorite). 

Unsurprisingly, the Russian woman turned out to be a total bitch and the first date with her was an unpleasant experience. I describe what happened under “Russian Girl #1” here. This was several years before I would notice a near-consistent pattern of problems from Russian women that I never experienced with any other race or nationality of women (though I still noted what happened, as I always do, for my records). 

On the other hand, the 19year-old, who I’ll call Courtney, turned out to be a huge victory. I did the standard Blackdragon one-hour first date, meeting up at a local Denny’s (she was 19 so she didn’t care) and just ordered soft drinks. We talked for the entire hour and we hit it off. She was extremely shy with a very quiet voice. At times I wasn’t sure if she was interested in me at all (some women are like that). Regardless, when I hit her up the next day to come over to my place, she agreed, and we were having sex within about 40 minutes of her arriving at my house. 

One hour and forty minutes grand total meet-to-sex, with only $13 spent, with a very cute girl who was almost 20 years younger than me. This was standard stuff at this point.

Even better, Courtney turned out to be one of the most long-term and enjoyable relationships with a VYW I have ever had in my life. She was very smart, extremely low key (and thus low drama and low jealousy), she had the exact physical traits I like, and we were very sexually compatible. I made her a low-end MLTR and saw her for over a year, consistently. Moreover, during that entire time she never once brought up the topic of monogamy or exclusivity. This makes her a unique exception, since even the most sexually relaxed women will eventually bring this up after a few months, requiring The Talk.  

While this was all happening my fishing expedition for some returning exes also worked. Of all people, crazy Selina responded to my text and was enthusiastic to hang out again. I actually hesitated to do so, judging from my numerous crazy experiences with her before, but she was a very hot 20 year-old who I wouldn’t have to redate, and I figured I already had my other solid women, so I said, “What the hell. 

Lesson Thirty-Three

If you manage the relationship correctly while you’re having it, you can almost always bring an ex-FB or ex-MLTR back into your life as long as you keep many months of radio silence after she leaves and are very patient.  

This set off a story so crazy that I have never discussed it publicly before and purposely waited until it was at least ten years old to tell it. 

Selina asked if she could spend the night since she needed a place to stay for two nights. She had some kind of dispute with her mom who she was living with at the time before Selina moved into an apartment with her boyfriend (of course she had a boyfriend; Selina always had a boyfriend). I reluctantly agreed (I hadn’t yet solidified the Cardinal Rules against having FBs spend the night) figuring it would only be two nights.  

I coordinated with both Selina and her mom to meet them and pick up Selina. I had met Selina’s mom two years prior when I was playing around with Selina the first time. Mom was around my age (I was 38 at the time), fit, and very attractive. (Yeah. Now you know where this is going.) 

Selina came over, stayed at my place for three days, and left without incident. Then Selina’s Mom started contacting me without me contacting her first, even to the point of sending me flirty messages. 

I can’t give any detail about this next part, but to summarize, Selina’s Mom apparently had a thing for me regardless (or perhaps because of?) the weirdness of me hooking up with her daughter. We eventually met up in a parking lot briefly and talked for just a bit. Two days later Selina’s Mom was over at my place and… yeah, it happened. 

It was a one-time thing, which was probably for the best. Pretty damn fun though. I also didn’t see Selina again for a while since she was more focused on her boyfriend. Again, for the best.  

But there would be more from those two and others in their sphere. A lot more. 

Around this time, Charlotte dropped a little bomb on me. One night, while in bed with each other, she asked me if she could be my official girlfriend. It had been over eight months, so I wasn’t surprised. She assured me that I could still have sex with all the other women I wanted, and she meant it (her jealousy was almost zero, which is why she was so wonderful). She just wanted us to officially identify each other as girlfriend and boyfriend. 

I still wasn’t ready for anything like this. A god damn girlfriend, OLTR or not, was the last thing I wanted. I had only been out of my divorce three years and wasn’t done being 100% free and living out all of the sexual fantasies I hadn’t experienced yet. I also did not want a girlfriend taking the focus off my primary purpose in life: my businesses, which were starting to do well again after the financially difficult year of 2009. 

In retrospect, I could have just solidified her as my high-end MLTR and given her the title of “girlfriend,” but back then I wasn’t 100% sure how to combine the term “girlfriend” with an MLTR (rather than the OLTR which is what it’s meant for).  

So, as sweetly and as lovingly as I could, I told her no. She cried a little bit, gave me a hug, and told me she understood. Within a few weeks she was gone. Not a LSNFTE since there wasn’t another man in the picture. She just wanted more. 

It was fine though. She came back a few years later. They always do. Plus, Courtney was essentially replacing her so I was still covered, and two more women would soon return. More on that in the next installment. 

20 Comments on “The Story of My History with Women – Part 19 – The Old and The New

  1. These entries are always really inspiring.

    Also, it’s good to know that it’s okay to call your top MLTR “girlfriend”.

  2. Also, it’s good to know that it’s okay to call your top MLTR “girlfriend”.

    As long as you only do it with one of them, and you’re really careful and do everything correctly.

  3. Caleb,

    Does having FB‘s make your main girl aka MLTR  or OLTR respect you more / help keep a more Alpha frame / make her think more highly of you ?

    Forget about all the other benefits

    This this itself  an important reason to keep 2 FB‘s minimum on the side ?

    One of my friends told me this actually           ” have a side chick so that your main woman is always on her toes ”

     

  4. Does having FB‘s make your main girl aka MLTR or OLTR respect you more / help keep a more Alpha frame / make her think more highly of you ?

    It keeps attraction higher and keeps betiazation at bay.

    This this itself an important reason to keep 2 FB‘s minimum on the side ?

    Yes and I’ve said exactly that to men with OLTRs many times. When you stop having sex with other women your OLTR (or MLTR, but it’s worse with OLTRs) will smell it on you and within 6-12 weeks you’re going to start encountering all kinds of drama, demands, and other problems from her.

    Monogamy is not conducive to a long-term lack of drama.

  5. Caleb,

    From your history / experience do you find  slim women require a different kind of game than heavier women ?

    I ask since I find slim women tend to be more conservative but your experience could be different

  6. Hey Caleb,

    Trying to wrap my head around a high-end MLTR vs an OLTR..For instance, would your frame differ from having a high-end MLTR vs OLTR? Such as with an OLTR: giving a bit more boyfriend behaviors than a high end MLTR? And I’d assume you can still have low tier MLTRs with a high end MLTR, but you wouldn’t be able to have two high end MLTRs because only one you call your “girlfriend” (if that’s what you agree to), am I thinking about that right?

  7. Caleb,

    Pardon me but how is this off topic ?

    This is about your history with women. And I thought you might share notes from your history with women which includes how women of different ages, races , body sizes behave.

    Sorry you feel that way.

    I’m waiting for the coronavirus to end so my work can open up before I join the SMIC btw. 80% of what I’m looking for from SMIC is business / income related so at this point it makes no sense to join.

  8. Trying to wrap my head around a high-end MLTR vs an OLTR..For instance, would your frame differ from having a high-end MLTR vs OLTR?

    Good question and I realize it’s a hard concept to understand.

    Any and all boyfriend behaviors for an OLTR are allowed (just don’t too far with them). But with a high-end MLTR most boyfriend behaviors are NOT allowed. A high-end MLTR is still an MLTR and thus you must adhere to the MLTR Cardinal Rules with them. You can’t see your high-end MLTR several times a week, nor go on a two-week trip with her, nor talk to her everyday on the phone, and so on.

    And I’d assume you can still have low tier MLTRs with a high end MLTR, but you wouldn’t be able to have two high end MLTRs because only one you call your “girlfriend” (if that’s what you agree to), am I thinking about that right?

    Right!

    Here’s the bottom line:

    1. You do NOT call your high-end MLTR your “girlfriend.” No. I’m just saying you can under certain conditions if you are very experienced and know what you’re doing.

    2. Having two high-end MLTRs is technically allowed but not recommended at all. (Again, if you’re a very experienced, strong Alpha you might be able to pull this off. Otherwise please don’t try it. Shit, even I would never do it.)

    3. NEVER have two women you call “girlfriend” at the same time, regardless of what they are. (Unless you are following hardcore polyamorous dating models that have nothing to do with what I teach.)

  9. Hi Caleb,

    Love, love, love these posts.  Well all your posts! Your 1-1 coaching has put me in almost too good of a position!

    I have two girls that are definitely H-MLTRs and it’s tough!

    ======
    CONTEXT OF GIRLS (Can skip)
    ======

    A- 22, zero drama, insanely sweet, submissive, even finding girls to bring over for threesomes. 18 months dating Seeing once per week usually 2 nights

    C- 26, stunningly beautiful, super intelligent and fun, has run her own businesses since 21, works hard and is very ambitious, family is insanely wealthy, Cooks for me and great in bed, bit more selfish than A but we just click. 14 months dating seeing once per week, more sporadically.

    =====

    MAIN QUESTION
    They are both wonderful for different reasons but the relationships have lasted so long and they are both so into me I am starting to feel guilty even though C knows directly I’ve been seeing A longer and A is aware I’m dating other girls not just as FBs.

    1 ) What does one do?
    2 ) How long can you keep it going/should you?
    3) Is there drastic action that needs to be taken?

    I’m just focusing on having an independent outcome and saying “well even if I lose both of them at least I’ll have more time to do what i want”. I know I can easily go and meet other great women.

    Sorry if this is too long but it’s just such good insight you give and this Double HMLTR thing is a high quality problem to have but your doing! 😛

    Really appreciate your help if you do have time to reply. 🙂

    P.s. A is too young now but both seem candidates for OLTR though I don’t want an OLTR for probably another decade (I’m 31)

  10. I have two girls that are definitely H-MLTRs and it’s tough!

    You shouldn’t have two high-end MLTRs at the same time. Make one your high-end and another one a normal mid-range MLTR.

    They are both wonderful for different reasons but the relationships have lasted so long and they are both so into me I am starting to feel guilty even though C knows directly I’ve been seeing A longer and A is aware I’m dating other girls not just as FBs.

    Then your feelings of guilt are completely baseless, groundless, irrational, useless, and are causing you pain for literally no reason.

    1 ) What does one do?

    Clean out your bullshit monogamy Societal Programming, take some deep breaths, enjoy what you have, and stop feeling guilty for no reason.

    2 ) How long can you keep it going

    A year or two before your first LSFNTE most likely.

    should you?

    Other than having two high-end MLTRs at the same time, yes!

    3) Is there drastic action that needs to be taken?

    Nope. Just make one a mid-MLTR, but that’s not drastic at all.

    I don’t want an OLTR for probably another decade (I’m 31)

    Good for you. You make me proud.

  11. As I had learned before, the problem with having just two women is that it’s too close to one woman, which is monogamy, and therefore unacceptable.

    Yeah. The biggest difference is between having zero women in your life and one. The next biggest is between one and two. Three is much better, and after that, its rapidly diminishing returns. Spoken in my late fifties.

  12. When Charlotte asked you to be her Boyfriend,did she told you that she loves you?Or she only asked you to be her boyfriend,without telling you that she loves you?

    When HBM said  first that she loves you,after how many months was that,since you made her a mltr?Did you say that you loved her back,or you saw her as a high end mltr and said:”Tell her that you care for her deeply and want to take things slowly, but that you want to be with her.(Extracted from the article: when to say i love you “.

    Hey Blackdragon,can you help me with this:

    If after 7 months of dating a mltr you love her and you say I love you,there are 3 outcomes:

    1.If she says that she also loves you-perfect.

    2.if she says that she doesnt loveyou-Downgrade her to fb

    3.if she says-that she cares for you deeply and wants to take things slowly, but that she wants to be with you.

    How should you proceed,in order to not be roped by someone who doesnt love you(?

    Should you wait for example 2 months,and ask her if she loves you,and if she say no or gives another answear liek the above one ,to dump her?

  13. When Charlotte asked you to be her Boyfriend,did she told you that she loves you?

    No. She was in her late 20s and was a little more mature about that; maybe she did but didn’t want to tip her hand at that point.

    When HBM said  first that she loves you,after how many months was that,since you made her a mltr?

    That’s a good question and I don’t recall exactly. Not very long. I’m pretty sure she was in love with me before I was official with her MLTR status.

    Did you say that you loved her back

    No because I didn’t love her at that point. She was still too young.

    or you saw her as a high end mltr and said:”Tell her that you care for her deeply and want to take things slowly, but that you want to be with her.(Extracted from the article: when to say i love you “.

    Yes, that’s very close to what I did.

    If after 7 months of dating a mltr you love her and you say I love you,there are 3 outcomes:

    1.If she says that she also loves you-perfect.

    2.if she says that she doesnt loveyou-Downgrade her to fb

    I wouldn’t do that. I don’t think I’d see a woman as just an FB who I was in love with and didn’t live me back.

    3.if she says-that she cares for you deeply and wants to take things slowly, but that she wants to be with you.

    How should you proceed,in order to not be roped by someone who doesnt love you(?

    I have never loved a woman who didn’t love me first, so I really can’t relate to the question. If I were to guess, I would probably continue to see her as an MLTR for maybe threeish months, then talk about it one more time, and if she still didn’t love me, I’d end the relationship (not downgrade, but end) and move on. I’m just guessing though.

  14. “2. Having two high-end MLTRs is technically allowed but not recommended at all. (Again, if you’re a very experienced, strong Alpha you might be able to pull this off. Otherwise please don’t try it. Shit, even I would never do it.)”

    Is this because of the time and energy it takes to maintain even ONE high-end mltr, with two being impractical? Or some other reason?

    “3. NEVER have two women you call “girlfriend” at the same time, regardless of what they are. (Unless you are following hardcore polyamorous dating models that have nothing to do with what I teach.)”

    Well, that’s confusing for me, as I always had categorized your systems as very polyamorous. That’s kind of the distinction for me between your systems (my preference), having multiple sexual partners who DON’T know each other’s names and interact (but they know I’m sleeping with other people). OR, the other standard polyamorous systems, where couples hook up with other couples, or people are in a 3-person relationship, stuff like that.

    Why d’you draw the line where your systems keep every partner fairly distanced from each other? Why don’t you practice or teach stuff like the 2nd type where everyone knows each other or multiple-partner pods? Is it drama reduction or something? D’you find the 2nd type of polyamory has huge issues that are unsolvable? D’you recommend anyone who teaches the 2nd type of polyamory?

    A lot of questions I know but I’ve noticed this about your courses for years

  15. “2. Having two high-end MLTRs is technically allowed but not recommended at all. (Again, if you’re a very experienced, strong Alpha you might be able to pull this off. Otherwise please don’t try it. Shit, even I would never do it.)”

    Is this because of the time and energy it takes to maintain even ONE high-end mltr

    Yes. Especially if they both identified as my “girlfriend.”

    Fuck. I’d hate that.

    “3. NEVER have two women you call “girlfriend” at the same time, regardless of what they are. (Unless you are following hardcore polyamorous dating models that have nothing to do with what I teach.)”

    Well, that’s confusing for me, as I always had categorized your systems as very polyamorous.

    Incorrect. Hardcore “true” polyamory is 4, 5, 6, 7, or more people, men and women both, all fucking and dating each other (heterosexually) with real lovey relationships with all of their partners. While this could fall into the MLTR model, this is not really what I teach, nor would interest most men in my audience.

    Instead I teach an MLTR model, which are not your girlfriends, or a single OLTR who is. None of that is “hardcore” polyamory.

    That’s kind of the distinction for me between your systems (my preference), having multiple sexual partners who DON’T know each other’s names and interact (but they know I’m sleeping with other people). OR, the other standard polyamorous systems, where couples hook up with other couples, or people are in a 3-person relationship, stuff like that.

    Right.

    Why d’you draw the line where your systems keep every partner fairly distanced from each other?

    I don’t. Polyamory is 100% compatible with the MLTR model I teach. It’s just that MLTRs are not “true” polyamory. Occasionally I get some polyamory purists who complain that “I don’t teach correct polyamory,” so those are the ones drawing the line, not me. All I’m saying is to not call multiple women your “girlfriend” at the same time. (One exception to the rule: You are an extremely strong and extremely relationship-experienced Alpha Male.)

    Why don’t you practice or teach stuff like the 2nd type where everyone knows each other or multiple-partner pods? Is it drama reduction or something?

    Bingo. The possibility for drama is too high for my tastes. It’s also a little complicated and I like simple. Plus, most men who do that kind of thing are beta males and I would just freak them out and intimidate them. It’s happened before.

    D’you find the 2nd type of polyamory has huge issues that are unsolvable?

    No. I think it works very well for a niche segment of people. I know many people who do “real” polyamory and they enjoy it thoroughly. It’s just not for me.

    D’you recommend anyone who teaches the 2nd type of polyamory?

    Not off the top of my head, but there are lots of polyamory groups on Meetup.com and places like that you could check out.

  16. “No. I think it works very well for a niche segment of people. I know many people who do “real” polyamory and they enjoy it thoroughly. It’s just not for me.”

    By ‘works well’ for the niche segment of people who enjoy true polyamory, is that with minimal drama?

    What are the differences in personality or tendency or whatever between someone who’d better enjoy your type of distanced multiple partners and one ‘girlfriend’, and someone who’d enjoy ‘true’ polyamory?

    I’d always kind of thought I would prefer your method because I get really jealous and insecure, but I have periods of being able to pretend I don’t care, and not meeting or knowing the others guys would help me hide any lapses in jealousy under a facade of not caring. Since they’re out of sight, out of mind.

  17. More importantly: one thing which has always bugged me about your systems–having an OLTR under your definition seems untenable. Isn’t there always the chance she could fall in love more with another guy she fucks, then you become deprioritized or lose her? There’s always someone more ‘alpha’ than you, right? Seems to me agreeing to only have fuck buddies is too unrealistic to ask for.

  18. By ‘works well’ for the niche segment of people who enjoy true polyamory, is that with minimal drama?

    No. It’s with an average amount of drama. If your number one objective was to minimize drama you would never be truly polyamorous.

    What are the differences in personality or tendency or whatever between someone who’d better enjoy your type of distanced multiple partners and one ‘girlfriend’, and someone who’d enjoy ‘true’ polyamory?

    That’s a good quesiton. I don’t think I have a specific answer. It’s mostly about preference, emotional needs, drama tolerance, etc.

    I’d always kind of thought I would prefer your method because I get really jealous and insecure

    That’s a serious problem you need to fix no matter what relationship models you choose (even monogamy).

    More importantly: one thing which has always bugged me about your systems–having an OLTR under your definition seems untenable.

    It’s perfectly tenable and millions of men are doing it right now, including me.

    Isn’t there always the chance she could fall in love more with another guy she fucks, then you become deprioritized or lose her?

    Open Relationships: Won’t He / She Fall In Love With Someone Else?

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