How Do You Convince a Poor Guy That You Really Do Like Him?


I’ve just started dating a man I’ve known for several months. We both work in an industry that doesn’t pay much. My salary is good but normal for this profession and then with the supplement of my alimony settlement, I’m doing very well. He, on the other hand, is an artist/professional who has a hard time doing the whole “normal” work thing. Suffice it to say that he is dirt poor. Just tonight, he asked in a meandering sort of way, why I would want to date such a poor guy like him when I could have a rich man. He knows I was married to a man who made good money and that my last relationship was with a rich man.

I like this guy. He makes me laugh a lot, almost constantly. He’s delightful. He’s kind and generous and giving. He is compassionate and intellectual and kooky. I haven’t had this much fun with someone in years. Our dates last seven and ten hours. We like each other a lot. And we’ve yet to sleep together. He’s even thoughtful when it comes to sex and doesn’t push me at all. Well, hardly at all. 😉 My point is that he’s just delightful — why wouldn’t I choose him over some schmo with a fat bank account but a slim personality? It seems obvious to me — why doesn’t it to him?

So my questions are: how do you convince a poor guy that you really do like him? Will it niggle at the relationship forever or can you both get over it?

Ready for Lasting Love?
Ready for Lasting Love?


What a wonderful question and a wonderful sentiment for the new year. I only hope you can spread some of that pixie dust on everyone around you, since you clearly know what relationships are all about.

But here’s the deal on your guy. He’s insecure. Insecure that he’s not a good provider – and insecure that a quality woman like you might not be open to dating him. Of course, there’s one other sentiment that bears mentioning, as much as we’d rather not acknowledge it: money actually matters in the long run. That’s why it’s one of the most common causes of divorce.

He’s insecure. Insecure that he’s not a good provider- and insecure that a quality woman like you might not be open to dating him.

That said, I’m not here to convince you that money matters. You’ve been on both sides of the tracks and you’ve made a great case as to why you prefer this man. So why doesn’t he get how amazing he is?

Well, why does anybody lack in self-esteem? Mostly because society (or parents or peers) have pounded the idea “I’m not good enough” into most of our thick skulls. So women who are overweight have to deal with overweight men who crave airbrushed supermodels. And men who are short can’t get anyone to give ‘em a fair shake. And men who have no money are made to feel inadequate.

I know it well. I never made more than $39,000 until I was in my 30’s. In 2002, I was answering phones at an online dating company while I put myself through film school….I remember one woman who dated me thru JDate that year. Great chemistry. Lots of laughs. Similar values. However, she, unlike you, Samantha, couldn’t get over the fact that I had no money. And since she was 32,  independently wealthy, divorced and eager to start a family of her own, she simply couldn’t wait for me to get my career off the ground. I was upset — but I understood. I was in no position to provide for her when I could barely support myself. I do remember leaving her with some of my favorite parting words, though:

”Those lawyers and bankers who you’re going to date might be able to provide for you now, but they might never make you laugh. They might never turn you on. They might never feed your soul. But one day, I WILL make more money.”…


But I digress.

It sounds to me like you and this guy are a pretty special match. And the only way for you to overcome his deep seated insecurity is to be 100% consistent in your messaging to him. EVENTUALLY, he’ll come to realize that you’re for real; that the bottom isn’t simply going to drop out from under him. Unconditional love is really the closest thing to a cure for shaky self-esteem. If you believe in him, he’ll believe in himself.

Unconditional love is really the closest thing to a cure for shaky self-esteem.

Two caveats:

1. If he only has momentary lapses where he confesses his insecurity, that’s cool. Reaching for the check, taking vacations, purchasing nice birthday gifts — all are going to be a bit of a struggle for him — and you’ll just have to be patient. However, if he’s beating himself up all the time, this could go deeper than money. And you’ll have to ask why this man is so averse to getting a real job. One thing I understand after seven years of screenwriting in Hollywood is that there’s comfort in noble failure. Follow your dreams and it’s hard for anyone to give you a hard time about it. But when those dreams become impractical or unviable, you may need a reality check. Which brings us to…

2. Are you SURE that you’re okay with a dirt-poor guy? Just know that if you stay in your profession and he stays in his profession, you may have to carry him financially. Partners carry each other all the time, but do ask yourself if that’s the life you want to live. It’s wonderful that you say that character is all that matters, but I’d be remiss if I failed to mention that it’s fair to desire financial stability.