Should I Date a Man Who Isn’t Motivated To Support Himself and His Family?

I have been seeing a man for 8 months. For 4 of those months he was staying with me, temporarily, because he was starting his life over after his divorce and had little income. I offered for him to live with me rent free, even though I thought it was too soon to be living together, and I haven’t been in a relationship for over 5 years before him. He is 56 and I’m 48.

Once the 4 months was up, I insisted it was time for him to move out, that I wasn’t going to support him indefinitely and I hadn’t seen him doing a whole lot to earn a living. He just started working in San Francisco for a friend who owns a business, staying with his friend and borrowing a car. The plan is for him to work there 3 weeks out of the month, and then come back to New Mexico to see me for one week. I know this can’t go on indefinitely, but for now at least he will be working and I will have my space back. He is hoping that I will find a job out there and move there with him. It’s not out of the question as I am interested in making some life changes anyway and have some family there. But right now I don’t trust his ability to really be a partner economically. I want someone who has the means and motivation to support himself and his responsibilities (he has 2 children and is struggling to pay child support).

If I were a psychologist, I might use a term like “enabler” to describe you.

I love him, yes, and he loves me–adores me, in fact. He is not going to disappear from my life unless I tell him to, so that is not the problem–keeping him interested is not an issue. Sometimes I feel overwhelmed by his attention and need to be with me all the time. You talk about unconditional love, as does he–but where does real life fit in with that? Looking at the possibility of a future with him, from where we are now, looks like a frightening and potentially enormous financial burden I cannot and will not take on. When is love just not enough? I don’t believe in trying to change a guy that I am with, either. And he loves me in a way that I have rarely been loved, so the idea of giving that up is so hard. But something in me does not trust him, based on his history and maybe some of mine too, so I feel very conflicted. I know it is unlikely you will be able to answer this given the volume of emails you must get, but if you can I would be so grateful for your wise advice. -Naomi

Dear Naomi,

If I were a psychologist, I might use a term like “enabler” to describe you.
But I’m not, so I’ll just answer your question point-blank:

Ready for Lasting Love?
Ready for Lasting Love?

You can’t change this man.

You’re right not to trust him.

Love is not enough.

For all I talk about the concept of unconditional love, I’m generally assuming an underlying level of stability: decent job, happy disposition, no addictions, rap sheets, or debilitating diseases, healthy self-esteem, etc.
Because you can have all the love in the world, but if he’s an alcoholic or bipolar or chronically unemployed, you’re getting on a ship that’s got a big, fat hole in the bottom. And you can’t be too surprised when that ship sinks, bringing you down with it.

It doesn’t take a relationship expert to objectively see the holes in your ship.

He’s unemployed, which is fair, given this moment in U.S. history. He hasn’t been doing much to earn a living, which isn’t quite fair.

This man is a child, looking for a mommy. You need a man who can stand on his own two feet.

He struggles to pay child support.

He’s now living in San Francisco with a friend and coming back to see you once a month. This doesn’t make sense economically for a man who has no money. Is this the only job he could get? Is this the smartest way he can save to get on his own two feet? Apart from him leaving your space, is this good for your relationship?

He overwhelms you with attention and needs to be with you all the time. This is the hallmark of a desperate person.


So let’s not beat around the bush here, Naomi.

Your boyfriend is a very leaky ship and the reason he clings to you so desperately is that you’re the only thing that can stop him from sinking.

It’s very clear what HE gets out of the relationship — love, support, shelter, money, stability, self-esteem, sex… It’s not as clear what YOU get out of the relationship.

As a dating coach, I often tell women to make compromises — smart ones that are consistent with your long-term goals. If he’s 5’7”, give him a break. If he makes $75K and you make $150K, give him a break. If he has bad taste in clothes, give him a break.

But you can’t give a man a break or compromise on his own pride, drive, or self-esteem.

This man is a child, looking for a mommy. You need a man who can stand on his own two feet.

Let him go and find a guy who has this man’s good qualities without the big financial and motivational questions. He’s out there, I promise.