September 21, 2017


Dating Older Women

Dating Older Women



So, you’d like to try your hand at dating older women? Got the old Mrs. Robinson thing going on?

You’re in luck! There’s actually a lot that’s different about dating older women compared to younger ones. Most men don’t realize that as women age their tastes for what they want in a man change as well. Here’s my top 3 tips for dating older women:

1. Know your Age

Yes, yes age is a “state of mind” but when it comes to women “Older” really is subjective. How old are you? Given the wide viewership of our articles, let me break down how the differences of women change as they age:

25-30 years old: This is really only an “older” woman if you are in your late teens to early 20s. Understand that women in this age range are starting to wise up to men and they’re likely seriously looking for future husbands. They will still be out to have a good time more often than not, but know that getting into a relationship with these women means they see you as having long term potential at the very least.

30-38ish Years old: This is the “last call for kids” age range and if you get involved with these women and have no interest in having kids (and they do) you’re an asshole. Seriously. Don’t waste what little time they have left so you can feel better about yourself for having a regular bed partner who thinks you could be the future father of her kids. Let them find their prince charming. Move on.

40-60+ years old: Be on your toes fellas, we’re in cougar country now! When we’re talking about dating older women, this range is what we’re really talking about. Some of you may be thinking 40-60+?? That’s too old! But you’re wrong. As Benjamin Franklin famously put it, “All cats are grey in the dark.” and there’s a lot of benefits age can bring to women. Besides, many of the hottest Hollywood stars from the past decade or two that you likely drooled over when you were a kid are comfortably in this age range now.

2. You Need to Convince Her

One thing that almost all older women have in common is that they know their looks have faded. They may still have confidence in their appearance, but it mostly only goes so far as to expect attention from men that are around their age or older. They WILL question your advancements if you’re significantly younger than them. It doesn’t mean they won’t love the attention, but when it escalates from simple compliments to communicating your intent, or even something physical, they will likely put on the brakes with an incredulous “Oh please. I’m much older than you”

So how do you convince them? Simple. You just tell them...explicitly. Actions can speak louder than words in some cases but make sure it’s clear that this isn’t just you giving them charity compliments: You’re actually interested in them. See below for an example script:

You: I’m sorry but you’re gorgeous, what’s your name?

Her: *Taken aback* oh please. That’s very sweet, but I think I’m a bit too old for you.  

You: No, and I’ll be the judge of that. I’m not joking, you’re the most stunning woman in here, *smile* and I think you know that. You have a confident way about you, it’s very sexy. I’m Dave, what’s your name?

Her: I’m Maria, wow you’re very confident. I like that too. But there’s so many beautiful women here. I think you’re just being nice.

You: *Get in close, put hand on waist and lean into her ear and whisper sensually* I’m far from nice…

Her: *Smiling* Ohhh…

This leads me to my last point.


3. They Know What They want

One of the great benefits of older women is that they don’t really play games and they know exactly what they want. They also tend to be appreciative of what you want in the bedroom...Women’s sex drives increase as they get older so you can likely expect a healthy libido being a big part of the relationship as well.

Make sure that you’re always honest with them about what it is that you want and where things are going. Don’t assume that these women want a serious relationship, many do not. Depending on their history they may have recently gotten out of failed marriage or long term relationships and have no interest in jumping into another. If you position your attraction to her as something more than just a mutual physical connection too soon, you may scare them off.
A relationship with older women can be a strictly physical thing for a long time before it evolves into anything deeper. Many times it will not, keep this in mind.

So there you have it. If you’re interested in more tips for older women and to go into a bit more depth check out the interview series I did with Rob Calabrese on attracting older women - Click Here


Dating Older Women

~ Derek Cajun

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