The challenges of dating an unemployed man

By Faeza
12 August 2016

Frustrated writes:

Should a woman date a man who is less financially stable than her? I am in love with a man who is a great person in every other way. But he has no matric, no job, no entrepreneurial spirit whatsoever. How do you sustain a relationship where the man is unemployed and has no formal educational qualifications while you are educated and financially independent?

I really don’t want anything but his love. But the point is; I want to go out and have fun. And I end up having to pay. I am okay with that, but he isn’t. I have a car. He doesn’t. I have a house, and he doesn’t. And I try my best not to make him feel like he is less of a person, but it is inevitable. Is this relationship doomed?

Linda Yende responds

Let me tell you what your biggest problem is – the future. See, your worry about current issues is justified, no doubt. But your biggest problem is, how long will things stay like this? Understandably so. You seem like a young lady with a good head on her shoulders. You have managed to look beyond the superficial and the obvious, and you managed to find love in a man many of your peers would never have considered. And for that, I must commend you. You were not even looking for potential. You were just looking for love. That is truly admirable. And it is great for now. But it comes with it’s own set of problems.


The biggest one, is his self-esteem. I don’t care how strong this man is, sooner or later, this is going to bother him. You go out for dinner and spend more money than he could make as a weekly wage, if he had a job. Surely that must hurt him. Interestingly, it is not what happens between you that will bother him the most.

It is the opinions of others. In our patriarchal society, nobody raises an eyebrow when a wealthy, educated man takes a poor, uneducated, jobless woman and marries her. But the moment the opposite occurs, tongues will wag. People will speak behind your backs. And even if he doesn’t hear what they are saying, he will know that they are talking. That is a terrible place to be, for any man.


Here’s another thing; he is jobless at the moment. But him getting a job is not going to change the situation. I mean, what are his career prospects? Surely, he is not going to get a middle management position, is he? So what can you do? Encourage him to study, so he can get a better job?

That will make him think that you feel he is inadequate, isn’t it? Encourage him to be entrepreneurial? Help him set up a business? The truth is, everybody knows that we are not all born to be entrepreneurs. Some people just don’t have that spirit. So setting him up in business might be setting him up for failure. Which will be even worse for his self-esteem.


You don’t mention it in your mail; what are his intentions? How did he lose his last job? Is he trying to get another one, or is he just happy being looked after by you? Is he being looked after by you at all? Does he love you? Or does he love elsewhere? Most importantly; what is his plan? Is he trying anything at all to change his current circumstances?

Everybody falls on hard times at some point. It is possible to go through a rough patch and for a man, it is great to meet a woman who will understand that. However, this rough patch needs to be exactly that. A rough patch. Not a permanent arrangement. Sooner or later, he needs to have a plan. Sooner or later, he needs to at least show the potential or willingness to make something of his life.


Why does he not have a matric? Did he drop out, or was he hampered by financial or family constraints. Has he expressed interest in going back and studying further? I must tell you, out of all the things you spoke about, the one that stood out for me was; no entrepreneurial spirit at all.

Had it not been for that phrase, I would have had a far more hopeful and positive response for you. Some of the most successful business people have no formal education and most have a history of struggle and failure, before they eventually became successful. So, yes, lack of formal education is not a guarantee of failure in life. But he has no entrepreneurial spirit.


Does he have a talent? A hobby that he is passionate about that can somehow be turned into a career? I am really trying to explore every single possibility, rather than focus on the negative only. See, my biggest worry with all of this is that, the moment his ego and his self-esteem suffer – and this is inevitable, the way things stand now – he will become angry and resentful. He will hate his life and he will resent you for making him feel that way.

Even though it won’t be your fault, he will blame it all on you. And that may lead to him becoming abusive towards you, just to ‘assert his manhood’. You don’t want to be in the middle of that kind of situation. You have the answers to the questions I have posed above. So, only you can determine what happens next. But, from where I sit, I really do not see a very rosy future for you guys. Unless he presents you with a game plan of some kind, I really don’t see a future for you two.