How To Date Women Over 33 – Part Two

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-By Caleb Jones

In the first part of this article, I discussed some of the advantages and huge disadvantages of dating women over the age of 33 in a get-to-sex-fast context. I described how women over the age of 33 take much longer to have sex with for the first time, and usually end up costing more money, no matter how good you or your technique is.

Today, I’m going to lay out the specific differences in technique that you must employ if you want to (or need to, due to age) take the extra time, trouble and money to date women aged 33 or older.

My first and most important piece of advice is to simply refuse to approach (real life or online) any women over the age of 33, unless you already know them personally in some way. That will save you a huge amount of headache and wasted time. Many years ago, I very reluctantly decided to completely boycott women over 33 from my regular online dating blitzes. Unsurprisingly, as soon as I did this my results skyrocketed, my meet-to-sex times dropped like a stone, my average cost of meet-to-sex also dropped, and my happiness increased. I wish it wasn’t so, since I genuinely like women my age, but that’s how it is.

If you do online dating, set your online dating searches to 18-32 and stick with that. These days, I set my default search to 23-27, and then go to 28-32 if I run out of those. There are isolated, unusual cases where I may message a woman or two over 33 for curiosity or testing reasons, but those are rare.

If you do daygame, if a woman looks like she’s 33 or older (and yes, I realize that’s hard sometimes since those older women often look so hot and/or young), just pass her by and go for someone younger. Those younger women will have sex with you much faster, with less effort, and with less money.

(I don’t do night game, so I can’t speak about that).

When you should go after women over 33 is if you know any women over 33 in your social circle or if you're a young guy in his 20s and look damn good.

If you’re a young, hot dude, older women will put you in a much different category than they will put a guy like me their age, and you can sometimes sex them quickly just as if they were in their 20s.

If you’re a guy of any age and go after a woman over 33 already in your social circle, it short circuits much of her ASD because you’re not a “stranger” taking her out on a “date.” You’re a “friend” and, oops! I just fucked my friend! Tee-hee! It’s easier for her to justify.

Barring that, if you want to (or must) date women over 33 in a normal context (daygame, online dating, or some other usual method), here are the specific techniques you should use:

1. Realize and accept in advance that it’s going to take longer, and adjust your actions and expectations accordingly.

I get a lot of emails from you guys complaining that women over 33 take longer to get to sex, while women under 33 don’t. Many of you guys get really pissed off and/or surprised about this. So, the first technique is the most important one. Realize and understand that for the majority of the time, you’re looking at 6-12 hours of face time before you get to sex, even if you do everything right, including everything in this article (unless your individual situation is unusual).

Accept this going in and don’t get upset, surprised, or beat yourself up when she doesn’t leap to sex at three or four hours like the wonderful women under 33 do. Always set your expectations accordingly.

Under my system of a quick, cheap, one-hour first date, followed by the woman coming to your home for the second “date” and having sex, this means that an over-33 woman is often going to need two or even three of these quick drink dates before she agrees to come over to your place. You may even need to buy a little food for her on one or more of these dates.

You should still attempt to get her over to your place for the second date regardless. The problem is the vast majority of the time an over-33 will balk at this, giving some bullshit ASD excuse about how it’s “too soon”, or it’s “not appropriate”, or how she’s “not comfortable with that yet”, or whatever.

When she does this (and most will), don’t push it. Just cheerfully agree to the second date at another cool bar or restaurant attached to a bar, and proceed as normal.

Be aware that when you pitch coming over to your place for the second date, you may even get a visceral, angry response unlike what you’ve ever seen with women under 33. I’ve had numerous women get upset and even offended with me over texts when I pitch this idea. Don’t let it bother you. Just smile and tell her you two will meet up at X bar instead. Don’t get into a conversation about it and don’t make it into a big deal, or else you’ll never see her again. Remember, you’re dealing with a woman with sky-high ASD, an overly inflated ego about how desirable she is, and mountains of bullshit anti-sex Societal Programming about how “ladies” and/or “gentlemen” behave on “dates.”

2. Dial down the pickup artist techniques.

While there are always rare exceptions to every rule, most PUA routines and other tactical techniques will backfire on women over the age of 33. With a woman who’s 21, you can routine the shit out of her and everything will probably be fine. She may even enjoy it. But, if you try that stuff on a today’s 37 year-old, you’re going to get a sour face at best, some choice words at worst. Often, you’ll lose her completely right then and there.

You still want to maintain the frame and vibe of a confident, outcome independent Alpha Male. Just avoid the PUA techniques as best you can.

Frankly, when you get really good at this stuff, you won’t need PUA techniques at all, for any woman of any age. I consider PUA techniques helpful for guys at the beginner and intermediate levels, but once you’re at the advanced level, techniques won’t be something you need. (I can’t even remember the last time I used an actual pickup “technique” or “routine” in order to have sex with a new woman).

3. Dial down the provider vibe to its lowest possible levels.

This is where it gets complicated, since I just told you to dial down the PUA techniques, and now I’m telling you to dial down the provider vibe as well. (See how much fucking work these over-33s are?)

If your goal is to find a monogamous wife or Disney girlfriend, then I’m not sure why you’re reading this blog, but go right ahead and dial up the provider with these women as much as you like. But, if your goal is to get to sex with minimal time, money, and effort, you cannot look or act like a Poindexter, or else you’ll be pressing down on her Make Him Wait button.

Over-33’s Make Him Wait button is much larger and more pronounced than women younger than her, and it’s much easier to press, even by accident. Therefore, when meeting up with an over-33, do things like:

- Wear a normal T-shirt and jacket (or similar), instead of dressing up like you would with younger women who have less ASD and provider-hunting objectives. Have your hair a little messier than you would normally have it on a date. You get the idea.

- Avoid all conversations about your work or your education. With younger women, this stuff is okay as long as you don’t go overboard. With over-33’s you shouldn’t talk about it at all. If she asks you about it, give her a very general answer and redirect back to her with a question of your own. (Note: This does not apply if you met her through some kind of work or business function).

- If you have kids, avoid conversations about them as well. Again, if she asks about them, give a very general answer and then redirect back to her. As I’ve discussed in my books, if you have kids, talking about how much you love them and spend time with them is actually a DHV that women will like, however for the over-33s, it’s also a provider signal that will press her Make Him Wait button.

By the way, I screwed this up for years before I figured out what was going on. On first or second dates, when I would talk about how much I care about my kids and how much time I spent with them, if the women were in their 20s, they'd get stars in their eyes and I'd get laid fast. But if they were over 33, their pussies would immediately dry up and I was instantly in "good potential boyfriend/husband" category and suddenly locked into the Make Him Wait™ cage. Not good. If she's over 33, shut up about your kids if you have them.

- Dial down the provider vibe in your online dating profile if you’re an online guy.

Doing the above will still take more time to get to sex, but it should take a few hours off of the time you’ll have to wait.

Important: Don’t go overboard with this stuff. You still need to be very polite and non-abrasive with her. Dial down the provider, but don’t go in there acting like Mr. Bash Badass. Again, that will work fine with women under 33, but women over 33 will be offended. Think “Polite Alpha”.

4. Have sex talk as usual, but don’t push it if you get any resistance.

Sex talk is still a critical component and you still need to do it. Normally, if you get resistance you need to gently push until she’s relaxed and talking about it. With over-33s, you can’t do this. If you get any resistance whatsoever, you need to shut up, change the subject, and leave sex talk for another time. If you push it at all, even politely and gently, you’ll never see her again.

For you daygame guys, I also recommend that you don’t talk about sex talk at all during the initial meet. There’s just too much possibility to flair up her gigantic ASD shields. Also remember to keep the sex talk non-directive, which is doubly-important for over-33s. And again, don’t push it.

5. Pre-sex, text her a little more often, but not every day.

This is a weird one that I only uncovered in the last few years. During the time between dates, if Ms. Over 33 doesn’t hear from you at least semi-regularly, she’s often going to assume that you’re a player and you’re having sex with all of the other women on the dating site or at the mall, even if you’re not, and that means you’re OUT. No, it doesn’t make any sense, but that’s how this works.

My usual advice is to not text a woman at all, unless it’s to schedule the next date or a pre-set comfort bombardment move. However, I found that with women over 33, if I don’t text for a few days, then text her to confirm our next date, I would often get a self-righteous text saying something like, “I think you just want me for some kind of friend with benefits and that’s not what I’m looking for, blah blah blah ASD blah blah provider hunter blah blah, I’m brainwashed with Societal Programming blah blah, I’m the most beautiful woman in the world blah blah.”

Again, I have never had this happen with women under 33, but it’s happened with quite a few over-33s.

The magic number that I found to alleviate this was to text an over-33 once every 48 hours during the time between dates. Not every day, just once every other day. Just send her a quick text, have a few back and fourths, and then move on. It’s also important that you end the conversation first, or else she’s going to think you’re too needy. Once again, with these over-33s it’s a constant dance between being more attentive than normal, but not too needy. (Are you getting the idea of why I tend to avoid these women?)

Over-33 Social Circle Game

Since I’ve said that hooking up with over-33 women when you already know them is much easier, I get a lot of questions on exactly how to do it.

I don’t consider myself an expert at social circle game, though I have sex with a lot of women this way (of all ages). The vast majority of the women over the age of 33 I’ve had sex with were via some kind of social circle game or work circle game. Others may be better advisors on this topic, but I can give you a few quick things I’ve learned.

1. Don’t have sex with women you currently work with, but the loophole is the “currently” part.

I’ve gone into detail about that topic here. Don’t ever have sex with any woman you work with, unless you absolutely don’t give a shit about your job. I consider this an unbreakable rule.

However, you can have sex with women you’ve worked with in the past, even the very recent past. I've had sex with women over 33 who I worked with, got their contact info, then stopped working with them for whatever reason (I quit, or they quit, or my project ended, or whatever), then I immediately hit them up for a quickie meet. This is very effective, and I’ve been doing this for a long time, even as a young beta before I got married back in my 20s.

2. There is no “technique” to pitching a date with women you already know. You just do it. 

Just tell her, “We should go grab a drink/coffee some time this week. Tuesday’s workable.” Like I said, you just do it. She already knows you, so “technique” is not really needed. Just confidence and outcome independence.

3. Business functions are a great place to meet over-33s.

There are other guys in the PUA community and manosphere who are much better at this than I, but I’ve done this a few times. Business luncheons, networking groups, seminars, workshops, conventions, and similar get-togethers are fantastic places to use some over-33 social circle game. I’ve done this and it works well. I even know two guys who use weekly meeting groups like Toastmasters or Rotary to pretty much run social circle game on over-33s. I consider it too time consuming for my tastes, but these guys do get laid.

4. Remember all the downsides of social circle game and be prepared for it.

Remember that you need to keep sex within your social circle on the down-low if you want it to be successful. ASD spikes into the stratosphere for most women when they hit 33, so most women this age you sleep with won’t want anyone to know what you and her are doing. Also remember that ongoing FB or MLTR relationships with multiple women (of any age) in the same social circle where everyone knows each other are going to be pretty much impossible, unless you enjoy drama. This is why I always keep all of my regular women in completely separate social circles and social strata, so they’re unlikely to run into each other.

That’s it! If you wish to embark on this journey with over-33 women, have at it. If any of you have other techniques that you’ve found reliably work on many over-33s you’ve been with, please share in the comments so we can all learn.

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