Some women in their twenties are very attracted to midlife men.  How can this be?  Midlife men have things like receding hairlines … we are often not in as good a shape as men in their twenties … the physical list of disadvantages we midlife men face when being compared to much younger men is a long list.  But women in their twenties who are attracted to midlife men don’t put the primary emphasis on physical characteristics – no.  They seek the things that only we in midlife can offer – stability, security, confidence, attentiveness, appreciation … knowing how to make a woman feel beautiful (whether she is, in fact, beautiful or not).


A lot of the input I received from this article came directly from one of my good friends – a very hot 28-year old woman whose name I won’t mention.  Me – I have only a limited amount of experience dating women who are more than ten or so years younger than me.  The best data point I personally have is the 28-year old Mormon woman … who I discussed in Types of Women – Religious.   She had three children, and had been divorced twice.  She had been treated fairly poorly by both of the men she had been married to – and both of those husbands were close in age to her.  What she found in me was someone who was very complimentary toward her … someone who treated her well, and appreciated her.  Plus she was a “pleaser” in terms of personality type (also known as a Caterer in the Types of Women definitions here) … she wanted to make someone happy.  [And it was obvious during our first date that she had what it took to make me happy.]  I noticed right away that she liked confidence coming from me – and so in the spirit of testing the limits, I promptly commanded her to remove her clothes during our first date, and she did so without hesitation.  ;o)   I’m not saying that all younger women would do the same – but under the right conditions, those who appreciate confidence might.

Straight from a 28-Year Old Woman
I asked my good nameless 28-year old female friend to comment on the subject of women in their twenties being attracted to midlife men.   She explained it to me in terms of a caveman analogy – where men in their twenties are like the Neanderthals, and midlife men are the Cro-Magnons.   Here is what she told me:

Think of it this way, let us suppose I am a cavewoman standing in the midst of a field in Europe, and I’m cold because my Woolly mammoth bikini is not doing its job.  On either side of me, there are structures for living – one the home of a Neanderthal and the other the home of a Cro-Magnon. The Neanderthal structure is clearly a home, but rough and crude … whereas the Cro-Magnon structure is made of more stable and solid materials.  The Cro-Magnon home has a distinctive roof and entryway and is simply the better structure. Certainly, the Neanderthals have fire, as there it sits in the middle of this crude structure, but look the Cro-Magnons have a fire encircled by rocks in the middle of their sturdy structure, and the heat is funneled to all corners. While the Neanderthals are still dragging women by the hair and leaving them for days at a time, the Cro-Magnon has learned to balance the responsibilities of home and hunting. Neanderthals use brute force dazzling displays of strength in their hunting, while Cro-Magnon forges weapons, traps, snares.

Neanderthal man dies out while Cro-Magnon flourished and morphed from an anthropological view into modern humans. One theory is simply that Neanderthal women started mating with Cro-Magnon man and while the two species once co-existed, the superior species kept evolving, growing, and gaining knowledge from the world around them. See, young men are like the Neanderthal – aggressive, insecure in all areas of life save sex, convinced of their prowess simply because age is on their side, inattentive, and generally lack the ability to balance life because they don’t yet understand the fragility of it all. Older men, Cro-Magnon in this retelling, spend more time cherishing life, have tossed away their bar fight mentality, are attentive because they are pleased by the idea of someone being there with them and they understand that life is forever moving forward and there is no going back so they have to embrace each day as it comes.

Problems arise because Cro-Magnon (older men) often feels the need to equip themselves with accoutrements and take on the airs of younger man and where obnoxious behavior in youth can be excused it simply cannot in men that have lived life and certainly know better if they possess even a modicum of intelligence. I could go on more and more but I’ll stop here and let you take in what I wrote. One of my friends has a 45-year-old boyfriend, she’s 32, and she says she enjoys the settled edginess of him – how secure he is in life without the arrogance of youth, but he’s still youthful enough to have fun with her …  and rather than him feeling disadvantaged because of their age difference, he makes lame playful jokes about her age. He’ll say, “I remember seeing Star Wars in the theater when I was 15 – what were you doing?” and then she’ll say, “I don’t know – getting excited about my new potty seat?”

Be sure to check out the Dating Advice section of this site, under Develop a Strategy for Midlife Bachelor Success – in the subsection where I discuss Use What You’ve Got …. Exploit Your Personal Strengths and Minimize Your Weaknesses.  Much of what is discussed in this MIDLIFE ARTICLE can be found in abstract form there.  We in midlife have money and confidence and security in our favor – you’ve got to be cognizant of those advantages, and leverage them wherever possible … particularly if you are chasing a younger woman.  The other thing to keep in mind is that you should definitely pay attention to everything discussed in the Midlife Bachelor Personal Makeover section. If you are going to successfully chase a much younger woman, you will need to do everything possible to optimize the way you look and also your attitude. Good luck!

READER FEEDBACK / COMMENTS: 10/19/2007: From Cyndi A., Age 45, Austin, TX: Many guys in their 20’s are chasing older women… They want confident women that know what to do in the bedroom.  Most younger women lack skills, I’ve been told.

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.