I’m 41.

Until recently, when a woman over 40 checked out my dating profile, the first thought that always popped in my head was “too old”–and then I quickly moved on.

I would literally think, “Why is she checking me out; we’re not even in the same generation.”I shared this revelation with my friend Heather who is in her 30’s and she challenged me:

“You ARE over 40 Alex. Your age range is from 26-41. Why do you date younger women but not women your own age?”

But they’re not my own age, I still thought to myself. They’re old–and I’m not.

(Can we say… self-delusional?)

I told her that I’ve always been attracted to younger women. But it definitely made me wonder, why do men, particularly as we age tend to go for younger women?

Is it because of Youthfulness, Looks, Energy, Vitality, Playfulness?

Based on our conversation, and just for kicks, I switched my age range to an upper limit of 45 and… lo and behold! It was like entering a secret vortex of hotness:

Women over 40.

I was a pioneer in unchartered territory, and these lands were certainly exotic, to say the least. I’m a visual guy–and I was definitely seeing visions! But I was noticing a lot more than just beautiful sights.

They were confident! They were direct! They were liberated! And they were HOT!

Incredibly hot!

Let’s see if I can distinguish some of the qualities I found so alluring in women over 40 that are often missing in women in their 20’s and 30’s:

1) Confidence

They have some major life experiences. Usually, they’ve already been through a marriage, parenthood and probably a divorce.

Having hocked their “golden ticket” (i.e., marriage)–the claimed key to all of their dreams and fantasies–they now realize that if it’s to be, it’s up to me.

They no longer need a man to fill some void in their life; they know what they want, and they’re not afraid to go after it! They are also comfortable in their own skin. They don’t do the whole bullshit routine that unmarried women do in their 20’s and 30’s.

They’re no longer trying to be the woman that will attract the man. They know their value, and they own their beauty, which radiates from the inside-out.

Having won and lost many battles, and having sometimes given too much in past relationships, they have learned to maintain the delicate balance between giving and receiving (i.e., they can sniff out the takers with a single whiff).

2) Direct

Many women in their 20’s/30’s allow men to transgress their boundaries–constantly–without sticking up for themselves. You will NOT see a woman over 40 make this mistake very often.

Here’s how the scenario often plays out.

Both groups might get somewhat angry, but they do so in very different ways. Women in their 20’s/30’s will most likely grin and bear it at first, hoping that their guy understands the subtle hints and psychic messages that are being sent in his general direction (feel free to laugh now).

But as time goes on and their needs go unmet, the resentment builds until–BOOM!–they react and the switch is flipped from passive to aggressive.

Often, they will justify their over-reactions by blaming their partner for not acting appropriately. Let’s just call this the indirect approach.

Women in their 40’s, by contrast, use the direct approach. When something doesn’t feel right, they lay down the law, upfront, and set clear boundaries for the future.

But here’s the real beauty: after they’ve spoken their peace, they’re done. The slate is wiped clean, and everything is hunky-dory again. Let that soak in for a moment.

No future backlashes. No re-hashing it a week (or several weeks) later.

It’s really over.

Love. Is. Present.


(Unless, of course, you’re stupid enough to transgress their boundary a second time; in which case, you are probably done.) It’s an amazing quality! And it’s incredibly healthy–for all parties involved.

No drama, just communication. Now, we could get into why women in their 20’s and 30’s use the indirect approach.

But, that could (and should!) be an article unto itself. I will merely say that they are afraid – of what exactly, I don’t know, but it probably has something to do with not wanting to rock the boat or create conflict within the relationship.

3) Liberated

Since most women who are over 40 have previously been married and are now single, there is usually an experience of having taken charge of their lives by ending a bad relationship. (Yes, women end most marriages.)

This is not insignificant. It’s so easy to just stay comfortable in our lives, even when we’re, admittedly, unhappy.


Because ending our relationship often involves a major upheaval of our entire life: moving out, figuring out what to do with children, splitting up finances, etc.

It takes tremendous courage to do so, and I give major props to anyone who has left a crappy marriage or relationship. There is no greater joy than the feeling of liberation after having lived in a cage for too long.

The irony is that, for most of us, we’re holding the key to our own cage! Once a woman–or anyone, for that matter–has gotten out of their cage, the last thing they are going to do is get stuck in another one.

Not only that, but they also have no desire to put someone else in a cage, either. Their liberation is liberating. For this reason, you can say pretty much whatever you’d like to a woman over 40.

She may not agree, but she’ll give you the space to be you. Isn’t that what we’re all looking for, anyway? Someone with whom we can be ourselves–whether that’s a potential partner, lover or a friend.

4) HOT

I could have gone with sexy, but… who are we kidding? Every woman prefers to be hot over sexy–so long as she knows that you value all of her attributes and not just physical ones.

When a woman has taken good care of herself throughout her 20’s and 30’s (physically, mentally and emotionally), and is confident, direct and liberated, there is a good chance that she is going to be spicy hot! 

Furthermore, she no longer feels the need to follow societal norms about sex, love, hooking up or dating. Without the need to strategize to catch a man, she does what feels right and what works for her. How liberating!

And isn’t someone who is liberated super-sexy? I mean, even if you’re not physically attracted to that person, they are still SUPER-SEXY!

Personally, I love when I can flirt and be myself around women. Some will tell me right off the bat that they aren’t interested in something uncommitted.

But, because they create a space to be open and honest, it usually means that we are still going to connect on some level: intellectual, friendship, co-conspirators of mischievousness… or something!

I’m not sure where all this is going to lead, but isn’t that part of the fun? The not-knowing. The discovery. The possibilities. 

The irony is that when I talk to my friends about all of this, I still catch myself saying, “older women,” even though we’re about the same age! Obviously, my mental construct still has room for growth!

Regardless of what happens, I do know one thing – my next girlfriend will definitely be over 40.