How To Date Women Over 33 – Part One

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-By Caleb Jones

I’m going to be a contrarian today.

For a long time, I’ve discussed the downside of dating women over the age of 33 if your goal is to get to sex as quickly as possible. I’ve expounded on this idea in detail in many other articles on this blog and in my books, but I will briefly summarize the problem before I get into the meat of this article.

The problem is that, generally speaking (and there are always odd exceptions), women aged 33 or over are not going to have sex with you within 3-4 hours of face time like I teach, even if you do everything right.

This is not my opinion, this is fact. I’ve had literally hundreds of men verify this throughout the years, including daygame guys. These are men who can easily have sex with new women very quickly as long as they’re under the age of 33. As soon as they creep up over 33, the time it takes to get to first-time sex expands, as well as the average total cost of getting from first-time meet to sex.

Before I hear some of you scream, here are the exceptions and workarounds to this problem:

1. If you are very good looking (six pack abs or similar) and are young or look young. In that one case, cougars can often put you into the “broke but hot younger guy” category, their ASD sharply drops, and you can possibly score with them fast.

2. If large amounts of alcohol are involved, as in with night game (sometimes). That 36 year old who’s downed three long island iced teas in the club at 2am in the morning is probably not going to be difficult to have sex with quickly. (This then begs the question, how many men in their 30s or 40s are going to be willing to hang out at dance clubs at 2am?)

3. If the woman is on vacation, far away from her friends and family (and husband or boyfriend if she has one).

4. If you already know the woman from your work or social circle. I have achieved fast sex with plenty of women over the age of 33, but the vast majority of them were women I already knew somehow. They were not cold stranger approaches via daygame or online dating.

Okay. Like when I talk about monogamy, I get a lot of resistance when I talk about this fact. There are only two valid arguments I get to this.

The first is; “Oh, you’re being too negative. There are some women who will do it. You just need to put in more numbers.”

I know it’s possible, I’ve done it. I’m saying that it’s very unlikely. I have no interest in going out on 25 first dates with women over the age of 33 to find the one or two who will have sex with me within 3-4 hours of face time. Particularly when these days I can go on just three or four dates with women under 33 who will have sex with me quickly. I don’t like to waste my time. If you don’t mind wasting your time, then feel free to do so.

The second is; “Oh, c'mon BD. So what if it costs me $150 and 10 hours of my time? What’s wrong with that? I don’t mind. I kinda like spending time with a woman like that.”

Okay, you don’t mind, but I do mind, a lot, and you’re proving my point. Again, I don’t like to waste my time or my money. I have no problem with spending money on women under certain conditions as I have discussed here and here, but not when A) I haven’t had sex with them yet and B) I have no idea if I ever will have sex with them or not.

Spending (or should I say, wasting) time is even worse, since I have no desire to waste any of my time, ever, for any reason. Time is the only resource I have that isn’t renewable, and spending 10 hours of it on a 33+ year old woman, who will probably vanish on me at the 9 hour mark when I really put my foot down about the sex thing, is not my idea of spending my time wisely.

Moreover, the older I become, the more adamant I become about not wasting my time, since I have much less of it than I did when I was younger. When I was 22, wasting my time with women didn’t bother me very much, but damn, I’m in my mid-40s now. I don’t have time to waste any more, and I have things to do.

The Good Things About Dating Women Over 33

Here comes the “However.”

Despite all the problems I listed above, which are real problems that bother me, I agree there are advantages to dating older women (“older” in this context means women aged 33 or higher). I am almost always dating at least one woman over 33 as an MLTR or FB, often women over 40. As I said above, usually these are women that I met via some sort of social circle game or as ex co-workers. Rarely has it been via online dating (though there have been unusual exceptions).

Here are the advantages these women have over younger women:

1. More stable schedules. One of the reasons younger women drive me insane is because their schedules, and their ability to maintain a schedule, are absolute nightmares. My younger FBs and MLTRs are constantly forgetting our scheduled appointments in the most stupid ways imaginable. This includes the very smart younger women with college degrees and real careers.

Younger women forget appointments, oversleep, get hung over, get sick, forget to charge their phones, have sudden problems with their kids, friends, or family far more often than women over 33. Women over 33 have all of these problems too (they’re women after all), but not nearly to the same degree.

As a matter of fact, my number one problem with my women life is them failing to meet scheduled appointments with me. As a time management nerd, this is irritating. (Quality problems, I know.)

2. More depth and intelligence. This is obvious, but it’s true. I’m able to carry on more “real” conversations with older women than with younger women. This is one of the reasons why I raised my minimum age to 23 a while ago, and may even raise it again at some point.

Unlike most older men, I don’t mind if a woman is a young, dumb airhead. It doesn’t bother me at all, provided she’s hot and doesn’t give me drama (she’ll be an FB of course, and nothing more). Yet, I still admit that having an intellectual connection with a woman in addition to a sexual and/or emotional one is nice.

3. More knowledgeable in “non-girl” areas. This is not about how smart or not smart women are; it’s more about their age and experience. If I start talking about international markets, currency devaluation, commercial real estate, or my last profit and loss statement with a woman who is 21 or 23, I’m going to get a blank stare, and then she’ll shrug and change the subject back to her. As I said, this is okay with me, but if she’s 35 I have a decent chance of her at least somewhat understanding, or even being interested in, these more masculine topics. It's a nice little bonus.

Don’t get me wrong, though. I’ve still had plenty of women in their 30s and 40s give me blank stares about these things. I’m just saying that your odds are a little better.

4. Emotional depth. If a much younger woman tells me she has feelings for me, or loves me, I know that this may or may not be a true and meaningful expression of how she really feels. It might be, it might not be. Even if it is, she’s prone to change her mind literally within a week or two (and this has actually happened).

Yet, if a woman in her 30s or 40s says something like this to me, it’s usually, not always, but usually more real. I can put more credence to it. Don’t be fooled though, she’s still a woman and she’s still biologically hard-wired to change her mind about these things eventually, but the odds of her maintaining these feelings for much longer than a woman 10 or 15 years younger than her are very good.

Even if a woman in her 30s or 40s dumps or LSNFTEs you (and they will, remember, they’re still girls), the way she’ll feel about you won’t change. She won’t be dating you any more, but she’ll still love or have feelings for you. Whereas that 22 year-old will completely forget about you in two weeks, since she’ll be “in love” with a new guy.

When the older woman returns to you (which she will if you do everything right), the bond is still there. When the younger woman returns to you, the bond is gone and she’s pretty much a low-end FB now.

5. They’re still super hot, as long as they don’t get chubby. I am not in the camp that thinks women over 30 are less attractive than women under 30. I’ve never felt that way, even when I was in my 20s. As long as they don’t get chubby, which I realize is a big “if” in North America, women in their 30s are still smoking hot. Many women in their 40s are also very attractive. Now, we’re actually getting to the point where even some women in their early 50s are shagable, and I’m not talking just about wealthy celebrities, but normal, middle class women who’ve had a little work done.

As I’ve discussed several times before on this blog, both men and women are both getting more attractive as they age as compared to just a decade or two ago. I personally know many, and I mean numerous women in their 30s who are normal, suburban, non-rich, non-celebrities who look indistinguishable from 26 year-olds. I also know many women in their 40s who easily look between 30-33. This trend will continue and get better, barring the usual problem of Western women getting fatter as they age, which is still a huge problem.

If you ladies want to be hot as you get older, all you have to do is not gain weight, which is completely your choice. That’s seriously about 80% of it.

6. They’re more or less required for most older men. As an official “older guy” (I consider men over age 35 as “older”), I have dated women of all ages, from 18 year-old girls to women 50+. As always, as long as they’re trim, good-looking and low-drama, I’ll go there. However, I realize that most men are not like this. Most guys have a very specific age ranges they stick to when it comes to women. Some men like younger women and refuse to date women their own age. Many men refuse to date any women older than themselves.

In particular, many men my age don’t like dating much younger women and find these women irritating and/or immature. Other older guys are new to the dating or Alpha Male game and don’t have the skills or confidence to date much younger women yet. Both these groups of men must date women over 33, regardless of their downsides. It’s perfectly understandable. Younger women aren’t for everyone. Moreover, I didn’t start with younger women when I first got back into the game. Instead, I focused on women my own age and slowly moved down the age scale as I got better and more comfortable with the process.

In part two of this article, I will cover the specific techniques that women over 33 require in both dating/seduction and relationships that make them different from women ages 18-32. Stay tuned.

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