Do I Need to Be Financially Stable to Have Something to Offer a Woman?

married couple having problems with their bills

I lost my fiancee to cancer in 2016. I gave up all my savings and my income, and went into debt assisting with her bills and well-being until she passed. I moved in with my parents, and in the last twenty months, I’ve worked my debt down to a manageable number that allows me to live a little while still being frugal. I make five figures, so it’s been a challenge. After taking the time to heal and grow, I’ve started to date again. My goal is the privilege of marriage and starting a family. The caveat is that I’m almost thirty-nine and will live with my parents another year to clear my debt in full. I’ve met some great women, but despite my great personal and relationship qualities, they don’t have the patience to wait for me when there are other men available who can offer them more right now.

If I wait until I build enough disposable income to support a relationship without a need to be frugal, that puts marriage and a family potentially in my mid or even late forties, if you factor in the time it could take to meet a compatible woman and quality time as a couple before marriage. I’m not sure I would still want to start a family at that age, so I would be a liability to a woman that wants kids.

But if I date now to establish a relationship with an eye on marriage, and a family in my early forties, I anticipate a lack of opportunity and quality options because my partner would need to be patient and willing to contribute to many of our dating costs, or content with a limited lifestyle for a while. My experiences have taught me to value and prefer quality and simplicity over luxury and pageantry, and I’m excellent at showcasing my qualities, but other men have so much more to offer in terms of the stability and entertainment factor to woo women, which is evident when women leave me for them, despite my positive relationship qualities.

Am I doomed to dating purgatory?


Dear Jack,

I’m sorry for your loss and for the circumstances in which you find yourself. I also want to acknowledge the harsh truth of your analysis. You’re not wrong that many women will see your debt, your living arrangement and your age as three strikes against you. In a world where most prospects will give you only one strike, that could be crippling.

But instead of looking at this as if you’re doomed, I want to try to reframe this as a positive.

I haven’t walked a mile in your shoes, exactly, but I, too, was dismissed by someone I really liked when I was answering phones at JDate in my early 30’s. She was ready for marriage and kids and I was a few years away from being fiscally ready to settle down.

I didn’t blame her for her feelings. I did know, however, that my situation was temporary.

I may have been making $30K/year, was applying to grad school, and living with a roommate, but I was also hardworking, responsible, ambitious and not content with my lot in life. That sounds a lot like your situation.

And while you can understand why women would pass you up given the “entertainment factor,” that does not necessarily reflect the feelings of all women.

Should you happen to meet a client of mine — a woman who has financial security but has never been treated well by a good man — you may indeed discover that she values your consistency, your kindness, and your character while you see yourself to the other side of this trying time.

I’m not saying it’s going to be easy (to turn things around). I’m not saying the volume will be plentiful (money and stability does matter).

I am saying that if you acquit yourself with women the way you did in your email to me, I think you may be surprised and delighted with the woman you get.

I am saying that if you acquit yourself with women the way you did in your email to me, I think you may be surprised and delighted with the woman you get.

She’s the woman who loves you for who you are rather than what you possess, and I predict you will both be handsomely rewarded for your patience.

Good luck.

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  1. 21

    Hi Jack! I can identify. I lost my mom at 21 and finished raising my sister without much financial or familial support. We moved out overnight and I worked 60-70+ hours weekly in retail and food service for years to keep afloat. Im well read but securing health insurance in those days was a feat let alone my attempts to earn a degree which resulted in financial/stamina crash and burns. I’m 4’9″, pretty Italian American, feminine with long hair but lifestyle and price of healthy foods caught up with me and I gained a lot.  Holding down these 10-18 hour days on my feet 6-7 days week was grueling and my needs came last. Kept an open mind and over the years dated alcoholics, chronically underemployed, an agoraphobic, a part time employed pot head living with dad and going to community college, angry divorced dads, short, tall, fat, hairy, bald, socially awkward. I reserved judgement as I wanted in return. Men were often critical of my appearance while themselves being unattractive   and/or in great fiscal turmoil. I wanted someone like me who was at least trying to find a better life, and never wanted someone’s money to be held over my head. Fast forward to today I’m talking engagement with a boyfriend of almost a year. He’s 5’4″ chubby and a cutie like me. We take turns cooking healthy meals, are losing weight together. He’s a divorced dad who Doesn’t hate women, his youngest is still at home. He raised his three daughters and stepson after their mom turned into a midlife drunk/druggie. This held him back in many ways. He drives a 1992 Honda and owns his small business. Neither of us are flashy but are financially savvy and we can see once we combine households we’ll be on a path to financial security together. Despite neither having degrees we’re intellectually curious and always learning. I suppose either of us could have found someone taller, richer, hotter but I can’t imagine us finding a better match concerning humor, compassion, work ethic or fun. I bought WHD years ago and have been meaning to write to Evan to thank him for all his wisdom on this blog over the years. I truly believe I’ve found my best friend, soulmate and couldn’t be happier. Don’t give up Jack, as I almost did. Remember, “It ain’t what they call you. It’s what you answer to.” –W.C. Fields

  2. 22


    When I first started dating my ex-husband, he was in debt and had an unstable living situation (his ex and kids were in the process of moving states and he was living with an extended family member). He was around your age at the time.

    I knew his full story as we worked together, so I knew that the debt was accumulated because he had very premature twins who cost a lot of money in infancy and early childhood – and beyond – and because he wanted to maximise opportunities for his kids and ex (who didn’t work because of said burden, and they had a third child too). It helped that I already had strong feelings for him, but when he opened up to me to explain his financial situation after about a month or so (he certainly didn’t throw it in to the conversation on the first date), it didn’t ‘scare’ me at all. I actually felt closer to him. I’m a sucker for vulnerability 🙂

    This was despite the fact that I was debt-free (in fact, had significant savings), much younger and with no kids/’baggage’.

    I had no issue ‘taking this on’. I didn’t judge him, as what he did was, in my mind, the right thing. Also, who am I to judge without having walked a mile in his shoes. He prioritised the needs of his children and family over wealth building. That was understandable under the circumstances.

    What did become an issue for me, is that as our relationship progressed, the kids got older (and less of a financial burden), he got promotions and a raise at work, he wasn’t open to my suggestions about saving and about being mindful of money. He was gambling, bought an expensive car, wanted to go out multiple nights a week etc. etc. I had given him a loan as I saw it as a way to help him out so we could start building a life together. While he was grateful and he did pay for many things in exchange, it was highly frustrating that he wouldn’t take my input with regard to money, given the full background.

    So there are definitely women who will be okay with your situation. Maybe go for younger women who can still remember what it’s like to live at home (I had only moved out of home 4 years earlier when I started dating my ex), and who have some time for you to get back on your feet, before they need to worry about their biological clock.

    But once you’ve found them, please try to be mindful of their input and grateful for their generosity of spirit. It’s easy to get complacent and take someone for granted as the relationship progresses.

    1. 22.1

      I think that’s a very good point, Marika.   It leads back to an idea we talked about earlier – wanting the person who wants you.   This doesn’t mean that a woman should want every awkward geek who approaches her, nor does it mean that a man should want every woman who expresses interest in him.   But rather, to not pine after people who don’t want us and to choose someone who feels about us the way we do about them.   I obviously don’t know the inner workings of your past marriage, but when I hear a story about a man who disregards his wife’s feelings about financial matters, it’s a strong indicator to me that he doesn’t value her, period.   Or at least, not enough.


      This relates to what Gala and I were discussing above, where she suggested that Jack choose from among those who aren’t put off by his current circumstances.   It’s not that I disagree entirely with that, as long as within that subset of women, he can find one he would want to be with if his circumstances were better.   So that one day, when they ARE different, he isn’t tempted to trade-up.   Failing that, I’d follow Olongapo’s advice to focus on self-improvement for the time being, though without the obvious fallacy of applying Briffault’s law to humans.   Because, of course, anyone with eyes can observe women who stay in relationships well past the point where they’re not getting any advantage.   Women may do so due to love, hope, fear, the sunk-costs fallacy – in other words, anything related to human psychology 😉

      1. 22.1.1
        Mrs Happy

        Dear Jeremy,

        why tell Jack to focus on self-improvement “without the obvious fallacy of applying Briffault’s law to humans”?

        1. Jeremy

          Mrs Happy – Because self improvement will help him. And focusing on briffault’s law will make him miserable.


          Marika – point taken.

      2. 22.1.2

        You don’t always have to keep flogging that same point to me over and over, Jeremy. I just wanted to reassure a good guy that there is someone who will love and accept him for who he is, using a true story. And encourage him to cherish her.

      3. 22.1.3
        Mrs Happy

        I wonder why people think primarily of women w.r.t. Briffault’s law (well, aside from his animal studies) – as the theory when stretched to humans is surely completely gender fluid.

  3. 23
    S. (with a period)

    Wow.   Jack I commend you.   Like others, you can find women who will want you as you are now.   But consider Marika’s point about whether the woman you are in a challenging situation with is the same woman you will want when things are better for you.

    Gosh, I go away from this place a few weeks . . . I’m not of the economic class of most of the folks here.   It is harsh to read the words.   Jack, you can find the right person for you.   As for the harshness here, some of you may see it as truth, but I have no words for it, especially in response to such an open, heartfelt letter. Truth is fine, but how one says that truth matters almost as much as the truth itself.

  4. 24

    I’m sorry for the loss of your fiance and the future you had planned together. It just stinks that in our country devastating health issues often lead to devastating financial issues and I am sorry for that as well.

    First, I don’t think that you are financially unstable. You experienced an almost predictable huge financial hit. But you have a plan to pay off your debt and get yourself into a better place financially. On top of your continuing commitment to you fiance when the for worse part of “for better or for worse” hit, your discipline in dealing with your finances is admirable and something that a future partner will see respect you for.

    There were two things you wrote that drew my attention because they may mean you have some limited thinking that is affecting your chances of achieving your relationship goals.

    “If I wait until I build enough disposable income to support a relationship without a need to be frugal, that puts marriage and a family potentially in my mid or even late forties. . .”

    “But if I date now to establish a relationship with an eye on marriage, and a family in my early forties, I anticipate a lack of opportunity and quality options because my partner would need to be patient and willing to contribute to many of our dating costs, or content with a limited lifestyle for a while.”

    It sounds like your vision of marriage family life includes spending a few years being able to have a carefree lifestyle with your wife before you have kids, then once you have kids you expect to be the primary breadwinner. Or maybe you feel you need to purchase a house and have X number of dollars in the bank before you have kids. Maybe this was the plan you and your fiance had and by default it has become the script you want to run going forward.

    The answer for you may be to expand upon the acceptable visions for a future family. For instance that may involve being ready to have children soon after getting married while you and your wife are still renting. Or it may be letting go of the idea that you should be the primary breadwinner and marrying someone who makes a good living and plans on working full time after kids. You certainly have the skills necessary to adjust expectations and come up with acheivable goals.

    Good luck to you on your journey.

  5. 25

    I know women who do not need a man to support them financially, but who need to know that a man will be there for them emotionally. I personally don’t feel comfortable expecting my date to be responsible for my financial needs. In fact I would not date if I couldn’t afford being on a date. If we were married, I think I’d still carry the same attitude. If a man offers financial gifts or support when needed, that is fine for as long as it does not put a leash on my neck!

    You see, I don’t have money and so, I don’t expect from anyone anything I don’t have to offer.

  6. 26
    Janet Simpson

    My current boyfriend is $16K in debt, and it’s because of his health. He suffers from a number of chronic pain issues. He’s required hospital care, 3 rounds of physical therapy, acupuncture, soft tissue therapy, etc. A doctor of his tore up his gut with ibuprofen and now he has small intestinal bacterial overgrowth and IBS. The guy has debt because we live in an area with a huge cost of living and he has zero secondary income as a man at 42 years of age. Neither one of us wants kids. He has a car loan that he pays off every month. It’s really obvious to me that he is financially responsible. He’s just been hit by hard times. Now if I saw 3 Harleys in his parking lot, Armani suits, and all sorts of other things that show that he has trouble handling money i would be concerned. But I cannot fault someone for being in pain and seeking help. I think it’s important to find out why your partner got into financial hell, and if they have a plan for getting out of it. I don’t advise just dumping someone over it. Find out why the debt exists. They could be just as frugal as you are

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