The Difficulties of Dating Women In Their 20's Compared To Their 30's

I’ve always had a theory that at a certain point in everyone’s life they stop developing and they start coping. Without a serious life altering event, it’s unlikely that most people will truly change after their mid-twenties. They may adapt, but they won’t really change. I’ll give you an example: after a woman is about 30 and she realizes that she has trust issues she typically reacts a certain way. She will either resolve that she has trust issues and project that onto the people she dates, expecting them to deal with it, or she will choose to suppress her trust issues because she has found that it negatively affects her dating life. As you can see, she either doesn’t take any action at all, or she adapts to get the desired result. However, those trust issues are still very present within.

I was asked one time if it gets harder to date as you got older and I responded, “Yes, for men it is. For women, it’s still a little unclear to me.” I don’t believe in generalizations but if I was forced to answer that question, I’d say that the nature of dating and relationships is cumulative and progressive and for that reason it makes it harder for women as they get older.

As a man, by the time I’ve reached my late 20s I’ve had a significant amount of experience dating. I explained to a group of women in a recent discussion that at this point in my life when I make a mistake or do something wrong in a relationship, I’m fully aware of those actions. I’ve been in the dating world since adolescence, lying, cheating or being too distant aren’t ignorant mistakes a man makes – he’s very cognizant of his errors. Most men are also logical lovers; we believe that somehow we can control our emotions and feelings. We believe that if we adjust this or that, it will in turn adjust the outcome. This prevents most men from having a perspective that things will never change.

Well, in my experience from dealing with women as they near their late 20s, their experiences start to get the best of them. I think of the people with the most optimistic outlook on dating and relationships and I notice that they are typically younger. (I’m assuming these women are single. Married women who are nearing 30 or in their early 30s may not have been in the dating world for some time at this point.) As women get older, and because the majority of women are emotional lovers, they begin to inherently have baggage. Whether they’d like to admit it or not, they are carrying the cumulative transcript of their dating lives. Every time they’ve worn their heart on their sleeve too early on and had it crushed, they learn to not give too much and wait for a man to commit before them. Every time they’ve been cheated on, they’ve learned to be very careful to not give trust but let it be earned. Several examples could be given here, but I believe you get the picture. If women love emotionally, when their emotions get damaged, they can’t help but be affected.

I should say, this isn’t a bad thing. People should let past experiences guide their actions, but they just shouldn’t be held captive by them. Consequently, I think it’s harder, but I don’t know if I would say worse, to date women as they get older. I’ll explain. I would tell any other man, by the time a woman reaches the age of 27-28, her brain has completely developed and will not be developing anymore. That’s a biological fact. That doesn’t mean she won’t emotionally or socially grow, but her brain is done. The chances are she’s going to be the way she is at that point forever unless she has a life-altering event. 

Life-altering events are rare in nature and don’t happen often or to everyone. The woman you’re trying to date is likely very aware of her faults and if she isn’t, will never be aware of her faults. This might be a good thing for a man. If you’re able to know up front all the good and bad things about a woman, it may make out for a better situation – but not easier. For example, if you’re told by a woman that she is an absolute control freak and just likes things a certain way, that may be a good thing for a man who doesn’t want to have to worry about having to do everything and handle every detail. But in the same breath that partner is going to have control over his ever move because that’s a gift and curse of his woman.

Conversely, younger women are easier to date, but it’s not always the best situation. Younger women aren’t done developing and are subject to many more iterations before they fully mature or settle into their persona. It’s easy to date younger women because they haven’t figured it all out and haven’t grown their “olive tree” in the yard. (An Olive tree is an example of something that represents identity and tradition and is longstanding.) On the flip side, younger women are likely to go through many iterations of themselves between 21 and 30. 

The young girl you find easy to date today may one day change and leave, or not be the great fit you imagined she was before. That’s why I advise men to keep that in the back of their mind when they date younger. You may be falling in love with a person who is going to change and they may or may not still love you down the line. No one can say that all of these are absolutes; I’ve seen many who don’t fit the mold. I’m just speaking from my experience and from what I’ve noticed at a macro level. 

Each woman is going to be different. If I was playing a numbers game, I would go with everything in this article. In practicality, I have to just get out there and meet the woman and take it from there. I believe it’s true that older women are ready to settle down, get married and build a family. I believe that younger women are still trying to find out who they are and want to have fun at the same time. As a man, I’ve got to meet the right woman and see what the issues are – am I willing to sacrifice or compromise for those issues? 

Younger women may be all over the place but they love deeper and quicker. Older women may love smarter but may carry baggage from past dating experiences that turned bad. I really don’t know, all I can do is tell you that you can either play the numbers game or you can form a theory and test it out and see if it hold true. Personally, I would recommend taking it on a case by case basis.