Dating A Younger Man – Is It Worth It?


In a previous post, Doctor’s Orders: Date A Younger ManI filled you in on my 40-something year-old doctor’s relationship with a man in his 20’s, and her suggestion that I consider doing the same. I saw no problem with such a scenario as long as the relationship is healthy (hers is unhealthy).

Read along as I outline the pros and cons that come with older women dating significantly younger (10+ years) men. These women are sometimes referred to as MILFs (“Moms I’d like to f*ck), or cougars. Just for reference purposes, I have a tiny bit of experience. 😉

Here we go.

The Upsides to Dating a Younger Man

  • Curiosity. He’s more open to learning and exploring. The “ambitious” younger man will likely have more of an air of “intellectual curiosity,” versus a know-it-all air of superiority (because they’ve been there and done it all). You can introduce them to new things and ideas because they’re less set in their ways.
  • Creativity. His take on problem solving may be refreshing. Younger generations see the world through different lenses. A smart man who can think outside the box is an asset because of his fresh perspective.
  • Energy. He may be more fit, vibrant, and full of stamina. These qualities may give an older woman LIFE – a sense of renewal and youthfulness, especially if she’s newly divorced or fresh out of a long-term relationship with a man who is closer to her age or older. God forbid, the older man was prone to sitting on the couch every Friday through Sunday, with his hands down his pants.
  • Lightness of Being. In addition to feeling like you’ve been given LIFE, dating a younger man can feel refreshing because of his lack of baggage. Because he hasn’t accumulated as many experiences (like an ex-wife or two, or a long-term girlfriend who cheated) his heart isn’t as sheltered as an older man’s might be. He’s potentially more optimistic and fun to be around (in my experience). That open-heartedness and lightness of being makes any obstacle feel lighter.
  • Gender-ease. Having been in a relationship with someone who is 11 years my senior, I understand how some men are of the mindset that household chores like cooking and cleaning are still solely a woman’s responsibility. On the other hand, man who came of age in the 70’s or 80’s is more comfortable stepping outside of traditional roles, and may  be less competitive and more supportive of a woman who has a thriving career — AND have no qualms about splitting household chores.
  • Explosive Sex. I’m not sure if this is myth or fact, but I’ll comment on it anyway. Sex with a younger man is potentially more -(what’s the word I’m looking for?) – mind blowing with a man in his 20’s because his energy level is higher and he’s more conditioned as far as cardiovascular health and muscle tone. Ab muscles come in handy ladies! (umm hmm).

Now, some would argue that older men (30s and beyond) are more experienced sexually and are therefore more attuned to “making love” versus just having sex.

I thought so too when I was 25, but really, sexual chemistry is based less on age and more so on a willingness of both partners to express and meet one another’s needs. There are younger men who are smart enough to know that making the effort to meet a woman’s needs (whether she likes it slow, rough, kinky, etc.), that means winning. Sex becomes “amazing.”

Older woman

The Downsides to Dating a Younger Man

  • Ulterior motives. He may be using you – for several reasons: financial gain, a notch in his belt, a juicy story to tell his future sons about the older woman he bagged.
  • Financial instabilityHe’s probably broke. Reflect on your twenties. Did you (or do you) have an established career and financial footing? Not all women in their 30s, 40s, etc. have it together either, but they’re more likely to. In this situation, the woman will have to pick up the entertainment tab during the course of the relationship and be prepared to eat cheap! However, if you’re a woman who is willing to support her man and help him build, this may not be an issue, especially if he’s bringing something valuable to the table that you’re satisfied with, and the relationship is mutually beneficial. And of course, there’s always the chance that he is the higher earner.
  • Promiscuity. He hasn’t sown his wild oats yet. Many young men go through a period in their lives where their goal is to have  as many exciting experiences as possible. That quest for excitement often includes having as many sexual relationships with women as possible. There are several dangers here – including unplanned pregnancies, sexually transmitted diseases, etc.
  • Insecurity. As if aging and gravity aren’t enough to think about, the insecure woman may feel like she has to compete with younger women for her man’s attention. If she knows her role and is comfortable in her own skin, it may not matter if he ‘s constantly ogling women who are closer to his age.
  • Immaturity. Even the most mature young man will show his age from time to time.
  • Emotional attachment. Someone may catch “feelings.” This is a potential downside to explosive sex – the woman (especially) runs the risk of getting open emotionally. This is an issue when one or both parties agreed to be “friends with benefits.” Once that mutual agreement to “just have casual sex” is broken because one person falls in Lust, the relationship dynamic changes and it’s all downhill from there (potentially). This can happen regardless of how age factors in, but with a younger man the dilemma is intensified because no matter how great things start off, if he sees 3 or 4 children in his future, and the woman doesn’t want any more or is unable to conceive, there’s conflict and emotional turmoil.
  • Uncertainty. Seriously dating a younger man requires supporting him through his growth process. He may grappling with his decisions about what he wants to do with the rest of his life. Goals and career plans change. He’s still figuring it out and finding his footing. Indecisiveness is not the worse thing in the world, but dealing with someone who is in limbo requires patience and support.

I could’ve added one more bullet point for family conflict.

It’s risky to date a significantly younger man, hence the pros and the cons. However, the same is true for dating an older man, or any man for that matter.

The short answer to the title question is: it depends on what you want. If you’re looking to date a younger man, just employ the same standards you would if you were choosing an older one and make sure he at least has a sense of responsibility. If it’s serious, make sure he UPGRADES you. Happiness, above all else, is key.

Personally, the chances of me dating a man who is 10+ years younger than me are slim to none. After hashing out this post, I realize that the cons FAR outweigh the pros. (Revision: January 8th – 10:36pm) I was just sitting in Bareburger next to this middle-aged Caucasian woman who advised me that her friend was coming to sit at our table. The “friend” turned out to be a beautiful, young (28ish), dark-haired Hispanic hottie with a thick accent. One of the open mic performers recited a poem called “My Pussy Has Super Powers.” The milf turned to her young stud and said “I think YOUR penis has super powers.” I kept a stoic expression – face forward to stage, but deep down inside I was jealous!!! Never say never?!

What are your thoughts on older women dating younger men? Can you think of any more pros and cons? Comments are most welcome!

Categories: Advice, Dating Stories

Tags: , , , , , , , , , , , , , ,

17 replies

  1. I see that you’re taking a page out of my book by adding related articles. That’s great for many reasons. At least you’re a quick learner.

    Well, as I’d stated on your other article, I’m a MILF-Hunter, I always date older women. My current GF is 41 and I’m 30. So I’m virtually the measuring rod for older women younger men.


  2. ” The milf turned to her young stud and said “I think YOUR penis has super powers.” Don’t be jealous. Whenever a woman is really into a guy (especially if the sex is good) they say the most outrageous compliments. (*Side note; when you’re in that stage we can pretty much get away with some major stupidity.) Think about the compliments a man gives…


  3. You already know how I feel about women dating younger men. Great post! The pros and cons was a good way to break the game down


  4. Love this. Never done this. But I’m open. I’ve always gone older, but the last guy was too cheap to keep a steady supply of Viagra – is that a pro for younger men or a con for older men?



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