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

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

Evan,

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?

Samantha

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.

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Comments:

  1. 1
    Steve


    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.

    snip…


    why wouldn’t I choose him over some schmo with a fat bank account but a slim personality?

    snip….


    So my questions are: how do you convince a poor guy that you really do like him?

    Telling all of that stuff quoted above would be a good start :-)

  2. 2
    Jessica

    Just wanted to concur with Steve’s post. Great idea and advice.

    Jessica

  3. 3
    Ben

    It may seem crass, but you said it in your email. You haven’t slept with him yet.

    Sleep with him and he’ll ‘know you really do like him’

    He’s a nice guy, like me, and insecure.. that will make him feel much more secure. It’s what all guys need.

  4. 4
    Steve

    Evan,

    Thanks for posting that you have been on the losing end of dating because of your height and where you were at financially in your career at one time.

    I don’t have those issues, but I have my own.

    Reading that even a smooth dating expert making his living giving dating advice can be turned down helps.

  5. 5
    Steve

    Ben;

    My intuition is that if a guy feels insecure about money and class issues he will still feel that away even after his girlfriend sleeps with him.

    The insecurity will just shift from being able to “get her” to being able to “keep her”.

    It depends on him and how deep his insecurities run.

    No offense to anyone.

    I’ve felt awkward in situations where the woman a lot more money then I did, though I know I should not have.

  6. 6
    Damie

    Ben, you took the words right out of my mouth. Well, to be honest my response was more crass, but still in the same barpark. ;)

  7. 7
    Trent

    Ben, I agree 100%. To the original letter writer…nothing tells a guy you are serious like sleeping with him. Sorry, but it’s true. I’m not saying that every time a girl sleeps with you, it means she wants a long-term relationship. But if you’ve gone out several times, had 10-hour dates, and haven’t done the deed, he’s probably wondering where this is going. He may think you are trying to keep him at arm’s length. 10-hour conversations mean nothing to an experienced guy. It’s really no trick to get a hot girl to talk to you for long periods of time. It’s called “being in the friend zone”. What do you mean you haven’t slept with him but he “hasn’t pushed you…well, hardly at all”? My advice: next time you end a date, jump his bones :)

  8. 8
    m

    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.

    This might be a lie.

    OP also needs to know whether she’s dealing with the kind of man who will NEVER get over it; who will ALWAYS feel inferior.

    Now, she might not be. He MAY eventually comeo to believe in himself, with all that consistency and support and her giving 100% ALL the time (which is also completely exhausting for the woman when she’s not getting 100% reciprocally back, but if that’s what you all feel it takes…)

    But to not add that as a third caveat, that she really needs to be able to evaluate which kind of man this really is (perhaps some 3-month or 6-month professional goals they set together and this guy achieves, or that he sets and achieves, if he feels “sensitive” about goal-setting with her)?

    Is disingenuous. And potentially dangerous for the woman — particularly how much men harass us about how the biological clock is a ticking time bomb.

    Sure. Give him time.

    Just watch how he treats you during that time.

    And be clear in your mind about how much of YOUR time you’re willing to give up to see a change that HE is comfortable with (since it’s HIS feelings at issue here).

  9. 9
    m

    Sorry. Here, specifically, is what might be a lie:

    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.

    Apparently the site doesn’t do blockquotes. Mi scusi.

  10. 10
    Ron

    These two people have something special going on here. You all will F*CK it up by pushing them into the rack when it hasn’t happened naturally.

    To the letter writer: You’re a great gal. Wish I knew more people like that. What you have with this guy is hard to find. Just appreciate it and let nature take its course. Try to enjoy it and don’t worry too much about the future right now.

    If things are meant to work out, they will and in their own time.

    Good luck.

  11. 11
    downtowngal

    Ben said, “Sleep with him and he’ll know you really do like him

    He’s a nice guy, like me, and insecure.. that will make him feel much more secure. It’s what all guys need.”

    I get it – THAT’s why I’m single – if I sleep with more guys they’ll be convinced that I like them and keep calling me!!

    Seriously though, Samantha, you don’t have to sleep with the guy but have you even made out? If so that would certainly demonstrate your feelings; maybe, next time you’re together, when the moment is right, plant a nice, sensual kiss on him and see how he reacts.

    And tell him how you feel.

    If he still has reservations, then don’t waste any more of your time, it’s him and not you.

  12. 12
    S

    Well, I am the Samantha who wrote this and lemme tell ya . . . you all hit the nail on the head here! Specifically,

    “My intuition is that if a guy feels insecure about money and class issues he will still feel that away even after his girlfriend sleeps with him. The insecurity will just shift from being able to get her to being able to keep her. It depends on him and how deep his insecurities run.”

    Yep — so true — I slept with him but no matter what I said or did — he is an insecure person. He’s a slacker with problems that have nothing to do with me. After just a month of dating more seriously, it ended. But this is still really good advice — I think the key is to find someone who is where Evan was in his career, not someone who has issues with success/failure, etc.

    Thank you!

  13. 13
    downtowngal

    S –

    Thx for the update. Sorry to hear it didn’t work out but it sounds as if you’re doing ok.

    The key is to find someone who is happy with HIMSELF, and for most guys that’s being happy with their career. In this case if the guy was truly happy with himself his money issues wouldn’t stand in the way of your being together.

    I’ve known of guys who were ‘in transition’ when they met their wives and nice guys who didn’t earn a lot of dough and complained that was the reason they couldn’t get a date with a decent woman, yet couldn’t deal when a nice gal showed interest. so go figure.

  14. 14
    hunter

    to Samantha,

    this man sounds like me, before I knew all that I know now……hmmmmhh…

  15. 15
    Selena

    Oh, when the limerance wears off. Isn’t it funny how great someone seems until…you get to know them better? “Just Delightful” to “slacker” in one short month. Bummer.

  16. 16
    S

    So, Hunter, what changed for you? How old were you when you changed?

  17. 17
    hunter

    to samantha,

    ..almost seems as if, he, missed out on the opportunity of a lifetime…….

    You say what changed for me? I think therapy did it for me, only thing being that, men,. call it,. the study of female behaviour/dating code(information)…it is really interesting how females operate, and sometimes fascinating…

  18. 18
    Steve

    Hey Samatha;

    I just wrote the other day how cool it would be if we could see how people who write in end up resolving things. Thanks for posting a comment on how it went.

    This thread has a good lesson. Another person can relieve loneliness, but they can’t bring you happiness. They might be able to temporarily mollify someone else’s issues, but if that person wants to be happy s/he has to plug his/her own psychological holes.

  19. 19
    mrs. vee

    Pssssst…sorry to go off topic here, but I’m on a plane at O’Hare about to fly for 12 hrs (after we get de-iced). Just picked up the Jan 28 issue of Time. The theme of the issue is “The Science of Romance”. And incidentally, the cover is almost a direct ripoff of your first book, Evan. Looks like a good read for us all.

    Adios ’til luego!

    mrs. vee

  20. 20
    Evan Marc Katz

    And I ripped off the first book cover from Roy Liechtenstein. C’est la vie. Safe flight. EMK

  21. 21
    Maria

    Oh… I was there. I did the best I could to try to make him get it. I screamed it on his face. Somehow he was simply unable to believe I loved him. I heard many many times things like: Maria, I have nothing to offer to you. I mean, he is a barman, I am a corporate worker, but besides income or the type of job we had, he felt constantly less because I finished college and he didn’t. In the end while we were breaking up after being in a relationship for 8 months he said: I am sure if we stayed together you would leave me for an ambassador, some one like you.

  22. 22
    hunter

    to maria,

    Sounds like you were not wanted, and it took 8 months to see that.

  23. 23
    Javier

    If I am a poor guy and find a woman who has a better economic situation, as far as she is great and then she likes me  …I don’t let her go. It is not about money, it is about love….. If I have no money in my pockets, would do any thing to see her smile…. life is short and need to enjoy today…..Money can help you to do many things in life, but even if you are rich and feel alone, then you are the real poor guy….

  24. 24
    Mickey

    The OP sounds like a true sweetheart, & a rare gem. Considering that many women claim to like guys with confidence, I don’t know too many women who’d  be willing to stick with a guy who had confidence issues.

  25. 25
    Christina

    He chose a field that is pretty hard to so called “get rich”. If he just needs some reassurance and it isn’t a deep set emotional issue. He will make plans for the future and mention them to you after you reassure him. Gauge how much reassurance he needs and ask yourself willing to give that amount.

    It’s a 2 way street, he needs to work on his self-esteem and be motivated at the same time.  I don’t think you need to sleep with him to reassure him, it’s ridiculous. You sleep with him when you want to sleep with him, period. If he needs that to feel good about himself, honey, you are in deep trouble. Deep seeded issues alert. The truth is that you might not mind but he does and because he does, it will continue be a sore spot for him. Even if you pay, he might feel resentful. 

    My advice is test the water, take baby steps. 

    Good luck, he sounds like a nice guy so I hope it works out. 

     

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