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I have several female friends who are in their late twenties. When they tell me they are going on a date with a man who is their same age, I say, “Don’t do it.” And I really mean it. It’s funny because when I was in my early twenties I thought men in their late twenties had it all figured out. I thought they were so mature. They were beyond entry-level jobs and had perhaps already had one serious girlfriend whom they even lived with. These are grown men I said to myself. Now, well into my thirties, I see that any man under the age of 35 is mostly still a boy. It is just what our society encourages. Men are encouraged to sleep around throughout their twenties. They are encouraged to shirk responsibilities. I can’t believe I ever thought that a relationship would work out with a man in his late twenties when I was in my twenties. If you meat a man under the age of 35, just know that he probably hasn’t acquired all of the wisdom it takes to be a generous partner and a responsible human being. Not quite yet. And if you are out there looking, might I suggest that about 35 to 38 is the perfect age to meet a man. Any younger, they are still boys. Any older, you may face some other issues.


The young man wants to spread his seed

Men are all about novelty. They want to know what it is like to sleep with a lot of people. Women may not have as much as an urge. Maybe it’s because sex just isn’t as great for us as it is for men. Or maybe because we need that emotional connection to enjoy sex, so the desire doesn’t come up as often. But a young man probably won’t settle down until he has “spread his seed,” for lack of better words.


The twenty-year-old very much likes to party

In my experience, women tend to lose interest in partying hard and going out every night around their late twenties. Ironically, this is the age when men get most into it. They finally have the money to go out more, and buy drinks for women. They are proud of their jobs. They are finally confident in their appearance. They want to be very social. A man at this age does not really want to stay home most nights of the week watching television with one person.


He is still selfish

It can take a man a bit longer to learn the art of compromise. A man in his twenties might really like a woman, but he will like his freedom and independence more. If she wants to do something different then he wants to do, he might just go do his own thing alone and tell her to do the same. He doesn’t quite yet value compromising, in order to be with someone.


A man in his thirties is over the party scene

A man in his thirties has spent enough time at bars and clubs to realize you don’t meet anyone quality there. And, eventually these places become sad and boring. They’ve pulled the curtain aside and seen that clubs and bars are just full of people who don’t really know what they want and are lonely. He is burnt out on that scene. He would value good company and doing something simple like watching television over the company of hundreds of strangers at a bar.


A man in his late thirties has learned to compromise

A man in his late thirties has had several failed relationships. And, the cause of the failure may have been the same thing every time. He has probably already had several women tell him if he is selfish, he is self-involved, and he doesn’t know how to be generous. He has heard it so many times and lost so many good women over these issues, that he is ready to make a change.


A young man must be all about his career

The early twenties is a tough time for everyone in the career department. You have to work long hours. You have to do jobs you don’t want to do. You are still at the bottom of the latter, as an intern or an assistant. Men have a very hard time balancing work and personal life. During their early twenties, they must give all of their attention to their careers or they won’t work out. Women are better at giving their careers and their personal life equal attention starting at a young age. But not men.


A man in his late thirties should have it figured out

A man in his late thirties has probably established himself in his industry to the point that he doesn’t feel he must work late hours and on weekends just to stay relevant. Things are a bit more on autopilot. He has built up credibility. He can relax a bit more knowing his career is on solid footing, and he is ready to pay attention to his personal life.


A man in his forties might be bitter

Here is the issue with the man in his forties who has had too many failed relationships: if all of his girlfriends left him because he didn’t know how to compromise or be generous, and he still hasn’t fixed that, it’s because he did not take accountability. He probably thinks that women are just crazy or needy or demanding. He is incapable of learning that there really cannot be a healthy and happy relationship without compromise. He has the delusion that somewhere out there will be a woman who just wants to do exactly what he wants to do every moment of every day. And any other woman is just not right for him. This is obviously not true. No such woman exists. But some men remain boys forever and believe that she is out there.


Or, he may be in a rush

If you do meet a man in his forties who is actually very mature, but just hasn’t yet found the one, he might be in a rush to settle down. If all of his friends are married and having children, and he feels left out, and his career is settled and he feels that all that is missing is a partner, he might be willing to do anything to make it work. He will bend over to your every desire. It sounds appealing, but it isn’t. He might let you walk all over him. He might want to move this relationship very fast, and you will feel that getting married is a top priority to him—it’s more important than marrying the right person, or just being himself.


A man in his twenties can also be bitter

A man in his twenties can be bitter in a different way. He is fresh off of those first couple of serious relationships. The pain is still very real. And not enough time has passed for him to learn his lessons from that pain. So for now, he can just think that women suck. He can still carry that anger and resentment over failed relationships. Meanwhile, a man in his mid thirties has released the pain of those early failed relationships and instead just holds onto the lessons.


A man in his mid thirties is confident and secure

He hasn’t yet waited so long to find the one that he is starting to think he has to change his personality to make women like him. He knows who he is, and he is also confident in his ability to attract the right person. He is passed the point of being the selfish one in relationships, but he hasn’t yet waited so long to meet someone that he has become a doormat in relationships.


A man in his forties might be divorced

Here is another thing with men in their forties and up: they could be divorced, or have had relationships that were so serious they feel like they are divorced. They can have too much baggage. Most baggage before the age of thirty is not really baggage. It is just important lessons. But as things drag on and more serious relationships fail past the age of 40, it can feel more like heavy baggage affecting the man’s ability to open up and connect.


A man in his twenties will push boundaries

Men in their twenties don’t quite understand what fidelity means. They will push the limits. They will engage in conversations and activities that verge on cheating, not really knowing yet that they are cheating. They have to touch the stove and get burnt a.k.a. get dumped to realize they crossed the line. You don’t want to be the person who has to teach them they crossed the line.


A man in his mid thirties has learned the hard way

A man in his mid thirties may have lost a girlfriend whom he really cared about when he was younger because he engaged in emotional cheating or inappropriate messages with another woman. Looking back, it is very clear to him that he crossed the line. Around this age, he has truly learned what it means to be faithful and behave appropriately. Nobody has to hold his hand. He just knows in his gut.


Men in their forties can be stuck in their ways

Here is another thing about the older bachelor: he is used to doing things his way. Even if he does not want to be selfish, he has never gotten used to the idea of adjusting his actions or his behavior for someone else’s needs or feelings. The longer one goes without learning how to do this, the harder it can be to do.

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