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The Thirty-Something Dating Pessimist


They say dating after thirty is easy. But what they don't tell you is that dating after thirty is like riding a bike. But the bike is on fire. And the ground is on fire. Everything is on fire because you are in hell.

The assumption that dating becomes easier is probably not well thought through. I understand why they believe it should be easier, but they got it all wrong. As you get older you become more aware of who you are, what you want, where you are heading and you have settled into a nice job and life. You are more content than ever and assume that most people your age have also matured. So, dating should be easier by now... BUT it’s not!

Now here are a few examples of why women find it difficult (even impossible) to date in their thirties. I read about it and thought it was just stories made up by women who hate men until it happened to me! So I know it is real…very real!

The Mamma's Boy

You are a woman in your thirties content with who you are, you have a strong opinion and a strong personality, and you know what you want in life and what you want in a relationship. But here comes Mr. Know-It-All and he informs you that you have it all wrong. You don’t know what you want and that he can be really good for you and he can make you happy if you let him... But you have to let go of all your own beliefs.

First of all, I AM happy. Second of all, you still live with your mother who by the way, does everything for you. Perhaps you should consider leaving that relationship first before trying to convert me into your mother.

The Delusionist

Mr. Shrewd is over the moon on the first date. He just met a girl who has an opinion, a career, a life, hobbies, her own friends and she doesn’t mind not seeing him every second of every day. It is a dream come true! Until the third month. Everything you are becomes a problem and is now an issue. Your friends, your hobbies your job – it is taking up too much time. You must be next to him at all times; while he fishes, when he's washing his 4x4, or just watering the garden. Your job is now to sit next to him becoming less of yourself while he drinks every weekend away with his friends. It becomes compulsory to hold his hand while he is watching rugby the entire weekend and you are there to feed him and his friends. Your own friends have to take a backseat. Being me, I put a stop to this charade and I am shocked that I am now being resented for the things that made him like me in the first place!

The Saviour

It is the twenty-first century and we agree that we both like being free, careless, investing in our careers, and building a life that makes us happy and both of us are willing to take it slow. We are committed and happy and not in a hurry. We have our whole lives to do what we want. Then one night – BOOM! “Marry me! I want to have children and I need you to stay home and look after those children that I want you to have and by the way, I want a cooked meal when I come home to my beautiful wife. (Just like in the 1600’s) I can provide for you if you just let me… Just say yes!”

While he is waiting for his yes, I am waiting for reality to kick in again. I must have been in a coma and missed some years between yesterday and today. What the hell just happened?

The Sperm donor

When I was about sixteen – seventeen I decided that I was not all about having children. I was determined to put my career first and build a happy life for myself, and whatever comes after I would consider. I am now thirty-one and I still feel the same way. I am upfront about it because I feel the guy I am dating should know what he is getting himself into. Yet, you, Mr. Can’t-Say-No-To-My-Sperm, is telling me that I just didn’t meet the right guy yet and that you can change that. You try to convince me that I do want to have children especially if it is your babies… Two decades of being fully capable of deciding what I want on my own and you think you can change my mind within a split second with your golden baby-making sperms?!

The Rich and Infamous

Since you sat down all you have been talking about was your luxury house, your R1 million 4x4, a job that pays so well, and your purebred bulldog. Yet, you hand the bill to me or insist I pay half. This being our very first date, after you had ten beers and insisted that we share a meal because it would be cheaper.

I am not sure what you are saving your money for, Mr. Rich-and-Stingy, but I can tell you now that you will pay every last cent of this bill and as a bonus, you will never see me again!

Now, if you are a man and you don't feel intimidated by this - good for you! There are women out there that is waiting for you! Do not let anyone convince you that you are less of a man for being a gentleman! But if you read this and you think that I am crazy, this makes you uncomfortable or you feel the urge to stand up for yourself and protect your ego - you are probably one of the guys mentioned in one, two, or all of these scenarios. So just relax, we know it is a hard life for a man out there. Book yourself a pedi-and-manicure and we hope you feel better soon.


To all the lovely ladies out there who know exactly what I am talking about - this is apparently what dating came to and what men became. However, don't give up. Fortunately, there are still real men out there; a man that will fit your lifestyle perfectly and a man that will not ask you to be a lesser version of yourself.


The only advice I can give you is DON'T settle for less. Know your worth... and have the courage to wait for the person that will make you so happy and while you do so, at least enjoy your life on your own. You never know what this adventure might bring!


If you build a life you are content with, you can never be lonely.

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