Heavy Meddle: Introducing The World’s Least Assertive Gold Digger

Welcome Meddleheads, to the column where your crazy meets my crazy! Please send your questions to advice@wbur.org. Right now. Not only will you immediately feel much better, you’ll also get some advice.

Hugs,
Steve
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Dear Steve,

I don't mean to get ahead of myself, but I've just been on a first date with someone in whom I see potential. When I say that I see potential in him, I mean to say that I feel attracted to him and like there was a connection between us. Again, I'm not planning our wedding or anything, but I am ready to meet someone and start a family. Whether that means me, him and baby, or me, him and lots of cats is really up for debate, but the bottom line is this: I want to build a life with someone.

It is important to me that whomever I start this life with have a good job and be able to contribute at least as much as I can financially. I am not in a high-powered career, but I enjoy my work and have been at it for over a decade. I have job security, great benefits and make enough to pay my bills and put a little away for retirement. I'd be lying if I said that it wouldn't be great to be with someone who makes more money than me — that would be wonderful! But I'm not greedy and I have to be realistic that it is probably more likely that I will end up with someone who makes a similar income to me.

All that said, the man that I met tonight works a blue-collar job and wasn't shy about telling me he makes just enough to get by. After college, he was living off a legal settlement for a couple of years. It sounds like he wasn't super motivated to find a job until the money ran out. Once it did, he had difficulty finding a job, much less a job he would enjoy or that would even fit in with what he studied in school. He doesn't like his current job and doesn't sound hopeful about finding a better one.

It is important to me that whomever I start this life with have a good job and be able to contribute at least as much as I can financially.

Granted, I'm just getting to know this man and maybe I'll find that apart from our initial attraction that he isn't for me, but I wonder if it is "OK" for me to keep dating him while I have reservations about his future earning potential? It's more important to me than it ever was before, because I know now what my end game is — a committed relationship, a house, pets, possibly kids — and that life won't be free.

I also wonder how other women have handled situations like this; it makes me reflect on anecdotes I've heard of women taking a stand, telling their boyfriends they need to get better jobs, go back to school, get serious about commitment or any number of things. I've never been that "type" and now I find myself single and childless and nearing my late 30s. It makes me wonder if I should have asked for more and not feared being so demanding and needy.

I'm looking for guidance on how to proceed with this man but also future dates. I am mostly dating men that I meet online and I'm good about eliminating people before I meet them based on my criteria for a future partner. That all falls apart for me once I meet someone in person though — I lack the assertiveness to rule people out based on what I deem "shallow" reasons like money, especially if there is a connection between us. I don't want to hurt anyone's feelings, but I'm also not getting what I want.

HELP!

Signed,
Least Assertive Gold Digger Ever
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Dear LAGDE,

Believe it or not, as complicated as your situation feels, you seem to be in possession of your own answers. I mean by this that you appear to have done the necessary human work of reflecting upon who you are and what you want and even, to an impressive extent, what’s holding you back.

To review: you are nearing your late 30s and you know that you want to start a life with a man and may want children. You realize this will cost money and would like a partner who earns as much, or even better, more than you. You worry that this makes you superficial.

I wish I had the power to wave my feeble advice columnist wand and to decree that this doesn’t make you superficial. But you’re the one who ultimately has to issue that decree. What I’ll say, more broadly, is that you deserve happiness in your romantic life. And you should take those measures that give you the best shot at happiness. That means being honest with yourself about your needs, but also distinguishing between your needs and your wants.

It might be, for instance, that the connection you feel with this new man you’re dating will intensify, and will eventually come to seem more important than how much money he makes, or his professional ambitions (part of your misgivings about him seem to have to do with his lack of ambition).

It’s certainly true that some people find the partner of their dreams, and Hollywood has sold a lot of popcorn dressing up this idea in various gauzy costumes. But much more often, we settle down with people who are — like us — imperfect. The real question is whether their virtues outweigh those imperfections. Someone’s ambition and earning power do matter. But so does their capacity for emotional intimacy, their ability to listen, their willingness to communicate even and especially when the going gets tough. Will this person be a good father? Will he do the dishes stacked up in the sink? Will he be able to give you the support you need after frustrating day?

But much more often, we settle down with people who are -- like us -- imperfect. The real question is whether their virtues outweigh those imperfections.

One thing you’re struggling with, understandably, is the creeping sense that you’re “running out of time,” especially if you want to have children. Anyone who has dated into their late 30s can tell you that the pool of available partners does thin out, especially for woman, because men in our culture often decide to marry younger partners, while the opposite happens much less frequently. That’s a real concern, but I’d try not to let it be a cause for panic. Many women do marry and have children later in life these days.

As for whether you should keep dating this man in particular — or other men who don’t fit your “criteria” — you need to be as honest with yourself as you can. But if you do feel a genuine connection with him (and you wouldn’t be writing me after one date if you didn’t) you also have to give the relationship a chance to develop. It may be that this guy is a confirmed slacker when it comes to his work life. After all, people tend to present themselves in their best light on a first date, and the idea that he lived off a “legal settlement” for a couple of years doesn’t exactly scream “go getter.” But it may also be that his other good qualities come to feel more important than his earning potential.

My advice would be to get to know him a little better, and see if the emotional connection deepens. If it does, you have every right to let him know about your dreams and your concerns. In fact, you owe it to yourself. It would be a mistake — though a perfectly human one — to remain in the relationship out of loneliness, even knowing that he isn’t ready for the kind of partnership you want.

The whole idea of a 'gold digger' is just a patriarchal construct. What people want -- women <i>and</i> men -- is the security of knowing that their partner is willing to take care of them.

You make joking reference to yourself as both lacking assertiveness and being a gold digger. I don’t see it that way. I think you’re just doing your best to find someone with whom you can be happy. The whole idea of a “gold digger” is just a patriarchal construct. What people want — women and men — is the security of knowing that their partner is willing to take care of them. It does sound like you’ve reached a point in your life where you want to be more assertive about your desires. And you can do so without beating yourself up about having been a pushover in the past. Everybody has 20/20 hindsight.

What matters more is having a clear vision of what comes next. I got married at age 39, after a lot of stumbling around. And it happened not because my soul mate descended from the heavens, but because my wife and I realized that we didn’t want to live without one another (even if we sometimes drove each other nuts). We found love within ourselves as well as within each other.

You’ll do the same. I know it.

Onward, together,
Steve
♥

Okay folks, now it's your turn. Did I get it right, or muck it up? Let me know in the comments section. And please do send your own question along, the more detailed the better. Even if I don't have a helpful response, chances are someone in the comments section will. Send your dilemmas via email.