One thing I have learned over many years of dealing with people in a myriad of different life situations is that very often, people’s objections to things are purely contextual. That is to say that they object to things purely based on their current (and usually temporary) circumstances rather than on the actual facts and merits of what they’re considering.

-By Caleb Jones

If I tell you that college is a waste of time and money and is a horrible idea and provide all kinds of facts to back that up, if you went to college many years ago and ended up doing something with your life completely different than what you majored in, you’ll probably agree with me. However if you’ve just enrolled in college and are all excited and pumped about it, you’ll likely tell me I’m wrong and call me an asshole.

It’s the same with monogamy. If I tell you monogamy sucks and will ultimately make you unhappy and provide all kinds of facts to back that up, if you currently have a shitty marriage you feel trapped in, or you’ve recently gone through a bad divorce or breakup, you’ll probably agree with me (perhaps reluctantly, but you’ll still agree). However if you’ve just gotten into a brand new monogamous relationship with some new exciting person you’re head over heels in love with, you’ll likely tell me I’m all wrong and call me an asshole.

My point here is that in all the above cases, even with the people who agree with me, folks are forming their opinions not around the facts, but around the current and temporary context of their present-day situations. It’s a very irrational and chaotic way to live, but sadly that’s how most human beings are wired. In some areas of life, like politics, this human dynamic is so rampant that virtually nothing helpful ever gets done; everyone’s too busy being irrational and pissed off.

I’m human myself, so I always work very hard to make sure that I don’t fall into the same trap. I always do my best to form my opinions around facts and how the real world works rather than my current circumstances or current feelings, both of which are subject to change at any time.

This all brings me to the topic of dating women. Since women fall prey to this problem just like men do, you will find that many women out there will make judgement calls about you that actually have nothing whatsoever to do with you. Rather, they are about the women’s own current circumstances. Today I’m going to talk about the age of a woman’s family members, but this phenomenon can actually apply to all kinds of things in a woman’s life.

Younger women and older women both do this, but do this in a different fashion.

Younger Women –

When you’re a much older man, VYW (women under the age of 24) will often fall into the Type 1 or Type 2 categories (check the glossary for these terms if you are unfamiliar) purely based on the age of their parents. It’s the damndest thing and I’ve seen this happen many times. If you’re 38 and her dad is 39, she’s going to be grossed out and she’ll be a solid Type 1. But if you’re 42 and her dad is 57, the odds are much higher she’ll be Type 2 and you’ll have a decent shot.

I’ve even seen this with young women who were best friends or even half sisters. The girl with the normal, older dad has no problem fucking or dating older men, but the girl with the really young dad is horrified by the thought. “It’d be like fucking my dad! Ew!”

My point is the age of her dad is pretty much the only factor that shoves her into Type 1 or 2 status. Funny, isn’t it?

If dating sites actually catered to men instead of to women, perhaps they would require women to fill out a new field: “Age of parents”. All of us older dudes would know in advance to pass by any of those younger women who had unusually young parents.

Older Women –

This works in the exact reverse with older women, specifically women over the age of 35 or 40. They will be attracted or repulsed by you strictly based on the age of their children. What does the age of a woman’s kids have to do with you? As much as a younger woman’s father’s age, which is to say, nothing. Yet women will still use these factors to judge your sexual worthiness with them. I’ll give you a perfect real-life example of this.

Years back when I was going through an older-woman kick, I had a first date with a woman who was 42, and this was when I was, I think, 37. We talked about a few of the other people we had dated, and I mentioned I had dated a 19 year-old. She had no problem with this at all, and even thought it was a little funny. Later we had sex.
A few months later I was on a date with another 40-something; I think she was 43. Same deal, we talked about other people we had dated. I could tell she really liked me and we were getting along very well, more so than the woman described above. When I mentioned the 19 year-old, her face suddenly jerked upward and she looked at me in horror. “Why would you ever date someone that young?” It was clear she was very disturbed and turned off. I never saw her again after that first date.

The difference between these two women? The first one had 9 year-old son and a 7 year-old daughter. The second woman had a two sons, age 18 and 20. Ah ha! The reason I had freaked out the second woman so suddenly was because I had been dating someone as young as her own son. So just like a 19 year-old with a 38 year-old dad, I had grossed her out. Think I’m jumping to conclusions? This exact same thing happened several times with several women until I caught on to the pattern. (Sometimes I’m slow on the uptake.)

Once again, I was judged based on her personal context, something completely outside of my control and something I personally had nothing to do with. (I also implemented a rule to never talk about much younger women when on a date with an older woman, and I strongly suggest you follow the same guideline if you date a wide range of ages like I do.)

It’s all completely irrational, very unfair, doesn’t make any logical sense, and frankly it’s a little stupid. But it’s how people work. (Lest you think I’m picking on women here, men do this too, as many women can attest to.)

Another Observation About This – Women’s Height

I wasn’t going to talk about this in this particular post, but it’s so relevant to the overall point I can’t resist. For some odd reason, three out of the last four new VYW I’ve successfully dated were 5’9″ to 5’11”. That’s right. Three out of four. Weird huh? If I’m on an online dating site messaging women this young, usually the one who messages me back, at least lately, will be the tallest one in the group.

I blew this off as a funny coincidence, but as I was writing this post I paused and looked back through my spreadsheets at all the VYW I’ve had sex with since getting back into the game six years ago. Sure enough, taller younger women were very strongly represented, far more than the national average (considering the average American woman is 5’5″).

Could something as basic and irrelevant as a woman’s height also be a deciding factor as to Type 1 or 2 status? Could younger women who are much taller somehow “feel” older? Or more confident? And thus it feels more “okay” to them to date a much older man? Hm.

I honestly don’t know, and I’m certainly not saying older men should focus their efforts on taller younger women…but at least in my own experience there’s definitely a pattern that would be very hard to explain away by coincidence alone.

Take your own age, your own circumstances, and the type of women you like to date, specifically those in your target market. Then be acutely aware of the various contexts these women are judging you on. It’s extremely helpful information, and it could be costing you results if you’re unaware of it.

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