How Do I Date After My Divorce If I Think All Women Are Gold Diggers?

Rich elderly man with gold digger

Evan – First, I’d like to thank you and everyone who posts on your blog. Now that I’m back in dating mode, I can use all the help I can get. You recently addressed the issue of how to get over a broken heart. Well when some relationships end, there is not only a broken heart but also a devastating financial impact which naturally has an adverse effect upon one’s emotions. The advice for a broken heart is usually a mixture of “give it some time”, “he/she wasn’t the right one for you”, and “find a new BF/GF.” Over time, the pain dissipates, and if someone is reluctant to start a new relationship because of fear of being hurt again, then the “is it better to have loved and lost than never to have loved” words start flowing. It’s all good advice and most people, myself included, are able to dust ourselves off and enter into a new relationship after an appropriate amount of time. The broken heart I have dealt with. The “broken bank account,” however, is a problem that I have to deal with for the remainder of my life.


My ex was awarded 50% of savings/pension/etc. – no problem. I pay child support – no problem. I have to pay permanent alimony until the day one of us passes away – Big Problem! One of your posters mentioned removing all reminders of an ex as a way to ease the heartbreak. I cannot remove the reminder of sending my ex a substantial check every month. My plan to switch careers after the divorce was derailed because the alimony is based on my earnings potential. My plan to retire is a dream because my state does not recognize voluntary retirement as a valid reason to decrease an alimony award.

I have two issues. The immediate concern is I keep meeting women who basically live a life of leisure due to winning the alimony lottery. Once I realize their source of income, I lose all respect for them and view them as gold diggers and opportunists. Yet part of me realizes I shouldn’t view them this way because they’re only taking advantage of the laws of the state (the McDonald’s hot coffee in the lap scenario just popped into my mind.) I’ve been so turned off by the initial alimony disclosure that I never pursue the relationships further. I think alimony might be warranted based on the circumstances, but how should I dig a little deeper to find out if she is a money grubbing lotto winner or someone who truly deserves the alimony?


I would love to find “the one” and eventually re-marry, yet the practical side of me is extremely risk averse. It’s hard enough to enter into a relationship knowing your heart might be broken some day. After getting ^&* by the courts and the ex, it is extremely difficult to deal with the possibility that I might end up paying alimony to two women for life. Any advice other than find a rich woman or insist on a prenup? By the way, if this is posted on your blog I’d love to hear from some women who are paying alimony as well as the views of some women who are receiving alimony.

–Jaded Man


Dear Jaded,

This is an important question and I’m not going to muck it up by writing a long-winded answer. All I will say is this before I let our readers have a go:

Unless you want to protect yourself from finding love ever again, you’re better off not interrogating your dates, no matter how much you want to.

Emotionally, you are no different than the woman who had her husband cheat on her. You’ve trusted, you’ve been burned, and it’s hard not to judge each new woman by the unfortunate standards set by your ex. But I’ll tell you the same thing I tell every woman who doesn’t trust: “The next woman has nothing to do with the last woman.” They’re independent rolls of the dice.

And unless you want to protect yourself from finding love ever again, you’re better off not interrogating your dates, no matter how much you want to.

If I’m a woman, it’s not my fault that your wife sucked you dry, and I shouldn’t have to pay the emotional price for it. I shouldn’t be treated like a common criminal. I shouldn’t spend a second thinking about what she did to you. All I can do is show you, in word, and in deed, that my heart is in the right place. Beyond that, you just have to trust.

I think your story is very relevant to this blog, my friend, for two reasons:

1)     To show the man’s side of the story. Even as an advocate for women, I am VERY sympathetic to you and don’t think that divorce is fair to men. Division of assets and life time alimony is a very good reason why a man would not want to be married ever again and it would be hard to reason otherwise with him.

2)     To show women readers who reflexively think that you should give women a break that they’re being hypocritical. It’s easy to sit here and tell you to trust, Jaded Man; it’s a lot harder for them to let a man into their hearts and believe that the right man will do the right thing.

All I can do is stress that you should choose a partner based on character over intense physical chemistry.

It’s even harder to tell both men and women that there are no guarantees in life. If my wife takes off one day because she falls in love with another man, demands half of my money and custody of our daughter, I’d be shocked and devastated — but there would have been nothing I could have done to prevent it.

All I can do is stress that you should choose a partner based on character over intense physical chemistry. If you do that, you’ll be unlikely to find yourself in this awful position once again.

Let’s see what women have to say about it, but I think it would be hard to be unsympathetic to your travails. Really. It’s the worst nightmare of most guys and our women readers would be well-served to be sensitive to this reality…

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  1. 21

    @ Steve#21

    I agree, but Jaded (and men and women like him), are still going to be subject to the pressures of others who believe committment = legal marriage. And anyone who questions the validity of such a longstanding legal institution does so at the risk of being labeled “bitter”.

  2. 22

    In my personal and professional life as an owner/operator of a brick and mortar dating agency, I have never heard of life time alimony.   As a wife who has worked for most of my marriage – except when the kids were very young – unless there are extenuating circumstances, I think it is so unfair.
    I would recommend that anyone planning a second marriage seriously consider a prenup.   Marriages now do not seem to be as serious and committed as they were 25+ years ago.
    An unmarried 35 year old nephew voiced his concern about losing half his income and having a custody battle over any children in the marriage which is keeping him from making a legal commitment.   IMO these seem like valid fears at this time.

    1. 22.1

      Don’t get married. It’s not worth   it. If you do get a damp prenuptial

  3. 23

    JerseyGirl:  There’s got to be a midpoint… women that expect a guy to spring $15 for an entree aren’t “gold-diggers” by any stretch of the imagination, but that expectation is  nowhere near  a “right.”

    As for the OP… I had the same reaction as many of the other posters… “People still get awarded  alimony?”

  4. 24

    I’m not offended Steve but I don’t agree with you either. I don’t think the qoute hints at anything close to a john/hooker relationship. He isn’t advocating that women be with men they don’t love. He isn’t even advocating that men pay for the sake of paying. All he is saying is that the term gold-digger has been over manipulated. Like I said, a 20 year old girl marrying a 60 year old rich male, yeah, that’s a gold digger. You’re everyday average woman who gets invovled with your everyday average man..umm sorry, not a gold-digger.

    If a man cares for you, truly cares for you, he isn’t going to be stingy with his money. Now this isn’t the same as having to buy a woman big huge pricey gifts or live outside his means. But a man that considers you part of his life, a man that wants you to be part of his life, will share his resources with you. This is deeply biological.

    Time and time again women are told that men care about their looks, that you need to be a certain level of youth and fitness because men are “biologically” programmed to like that.  

    Women are biologically programmed to consider a man’s ability to provide. We need to know a man is capable in such matters. And a man that thinks your important or worthy enough to spend some of his resoures on is clearly interested in you.  

    If men don’t apologize for chasing women based on their looks, why should a woman apologize for evulating a man based on his money?  

    1. 24.1

      yes until the divorce. then she isn’t entitled to future money. simple

  5. 25

    I agree with Ruby(4) and Christie(12).
    There are SOOO many more women out there that aren’t living off alimony than those who are. If you are constantly meeting women who are “living a life of leisure”, then I think something is off with where you are looking.

  6. 26

    I agree it absolutely agree it’s a business arrangement. And where your sharing assets like a home and the liability of children.. Well let’s put it this way, would you invest in a business partnership without any legal documentation? I think people just need to refine their contract. Deciding what’s fair is easier while you still both one another. So prenup!   Of course this advice won’t answer the initial question at all. I’m curious though where is this place you live where all the women you meet have alimony and lifetime no less. The only women I know with life time alimony is my grandmother. Both my grandmother and grandfather are in their 90s still bitter as hell 40 + years after their divorce and I swear they’re both trying to outlive each other.

  7. 27
    Nancy Cieri

    Dear Jaded Man:
    I don’t know what state you live in but I received no such generous spousal maintenance from my cheating ex-spouse!   I concluded that although life is not fair, I am certainly blessed to be on the road to recovery, enjoying a love affair with myself(!) and not worrying about the future despite my own very vulnerable financial status and singledom.   One wise friend advised me through the turmoil of my divorce to not worry about what you are getting (in life) but what you can give. That thought makes all the difference to me daily.  
    Best Wishes  
    Manhattan Lady

  8. 28
    Christie Hartman

    @C (25): I too wondered why he is meeting so many women on alimony. The universe has a strange way of screwing with us – if you’re bitter about being cheated on, you seem to meet cheaters. If you’re bitter about paying uncomfortable levels of alimony, then “all” the women you date are getting it. What you focus on, you get.
    But as I said before, it’s hard to comment further without more details – how old he is, is his ex-wife ill, are there kids, how old are the kids, how much does he have to pay. It’s probably not as bad as it seems.

  9. 29


  10. 30

    C #25 & CH #30

    I suspect Jaded is attracting these women because he still has unresolved issues about his ex and his marriage. He’s afraid to move on and not ready yet, so he keeps picking women who are like his ex (a “money-grubbing lotto winner”). It’s a vicious cycle, but one of his own making.


    1. 30.1

      I suspect Jaded is in or beyond his 30’s and using some form of online or similar non natural way of meeting women. Women (men as well) at peace with their lives aren’t generally actively looking to find someone else to feel fulfilled. You’ll find them doing whatever it is that fulfills them.

      Best advice I can think of is for Jaded to quit thinking he needs a women and live his life. Become at peace with being you and doing you. If you find someone doing you, that’s great. If not, that’s just as great.

      As for the alimony, yeah, that sucks. I ended up here looking for for ‘how to become at peace with alimony’. The thought of someone mooching of me for life doesn’t sit well with me at all. Help someone get on their feet? Sure. Help someone that is incapable? I get it. Someone forfeited a career? It’s never to late to start again, but yeah, I see that too. Footing the bill for someone that’s lazy, opportunistic or both? Nope …

    2. 30.2

      When a person is in a long-term marriage, and that marriage ends badly, it is easy to date people who remind you of the person you were with for so many years. It many times is not a conscious choice.

  11. 31

    A friend of mine gave up his interest in his property to settle his divorce in lieu of possibly having to pay his wife lifetime alimony. She had been a stay-at-home mom for the duration of their 17 yr.  marriage and was 45 at time of the divorce.

    Possibly  Jadedman and his attorneys structured the settlement with the spousal support proviso to protect other assets? If he is a wealthy man with diverse business ventures, it could be in his best interest  that the “payout” to his former wife was in the form of a unvarying monthly cash stipend, rather than controlling interest in other income venues.

    And if he really does keep meeting women who “won the alimony lottery”, it’s likely because he is dating in the same socioeconomic circles in terms of business and wealth.

    1. 31.1

      who initiated the divorce?

  12. 32

    @Christie @Ruby   What you focus on, you notice anyway, that is for sure, sometimes whether it is there or not. I can’t imagine Jaded has a subconscious “alimony receiver” detector that clues him into women on alimony or that there is a set of personality traits or profile flags that only Women On Alimony have. But, if he is still angry at his ex, maybe he does read more into the women he encounters than is really there.

    The business side of a marriage is quick and easy to enter, and complex to exit. Anyone getting married should read through a template divorce agreement so they understand what they are getting into.   I was shocked when mine ended up being 26+ pages, and we had already divided all of our property and mostly agreed on “co-parenting” topics! To prenup or not is up to the individuals, but at least folks should enter into marriage knowing what it means.

  13. 33

    Just yesterday on Dave Ramsey a woman in her 2nd marriage called in because her husband insisted on keeping their finances separate; but he made twice what she earns and expected her to pay half.   Alot of people who have alot believe they never have enough.

  14. 34

    InsertPseudonym #33

    Jaded says he keeps meeting women who “basically live a life of leisure”.  If a woman is receiving lifetime alimony, chances are she isn’t working. so that would be one clue.  

    1. 34.1

      If a woman is receiving lifetime alimony, she also might be extremely underemployed due to taking decades off from her career for child rearing.

      1. 34.1.1

        I don’t know about CA, but in the state I live in, and most others I’m aware of, there is no such thing as “lifetime alimony”; alimony usually ends if/when the spouse receiving it remarries, and is subject to review and change, based on changes in financial circumstances of both partners. Child support normally ends when the child in question turns 18, marries, or is otherwise legally emancipated. Division of marital property is the only thing that’s permanent.

  15. 35

    With age comes experience and knowledge. Believe it or not you are in a far better place to make the right decisions for yourself. However, my advice is to try and stay as open and flexible as you can. So many clients in the past have tried to “replace” a past love and by being too stringent on the many characteristics that make up a human being they miss out on so many new opportunities.

  16. 36

    Very simple way to avoid major future alimony issues (should you marry & then unfortunately end up in divorce) – PRE-NUP!!!!!

    That being said, if this guy expects his future wife to give up or significantly curtail her career (which is what she uses to support herself financially & secure her future retirement), then he cannot expect to get away with not compensating her financially to some extent should they divorce.
    This is one of the reasons why I chose not to marry my ex-fiance – his idea of a pre-nup was an entirely one-sided deal that was all about protecting his assets & financial security, but not mine (any clauses about compensating me for thousands of dollars of relocation expenses and/or taking a 40% pay-cut to move to his city were deemed “not necessary” in his opinion).

    But this is not something you bring up as a conversation topic on a first (or second or third) date! It would totally put me off, to say the least, because the message that I would be hearing would be that the guy totally didn’t trust me, and was – quite frankly – a little too selfish/self-centered in his attitude.

    One thing to note – many (but not all) alimony payments cease if the recipient choses to re-marry. So all these “gold-diggers” may well not want to marry this guy because they would lose out financially.  If they aren’t particularly concerned about re-marrying, they might be quite OK with having a long-term relationship with this guy (assuming his attitude improves!).
    And then he wouldn’t ever have to worry about repeat alimony… 😉

  17. 37

    I’m in a similar situation as Jared and have the same practical considerations when I date. I disagree with Evan, if I date someone that won the alimony lottery, it is helpful to terminate the relationship quickly; they are not women that have pride in themselves nor the maturity to stand on their own two feet. Independent strong women are attractive. It says a lot about a woman that hoses her ex-husband for excessive and long-term alimony (short-term alimony is cool with me when the lack of it affects your children) just as it says a lot about a man who tries to get out of supporting his own children. Both are losers to avoid.
    As for protecting what you managed to keep after your marriage ends, it comes down to birth control (stop having kids with women), staying out of court (a complete waste of money, having integrity is cheaper) and avoiding marriage (too risky to leave it up to a future judge). Prenups are not iron clad unless they done with independent counsel with sufficient time before a marriage, I wouldn’t place much value in them. Men have to learn about family law also, it makes no sense to be ignorant of your rights should the right woman come along.

  18. 38

    I think I may be in the minority of experience based on the comments posted thus far. I was married for 17 years and had 3 children. I did the classic “quit school to support him in grad school” scenario. Our deal was that I would go back and get my degree once he got a job. After he received his doctorate, he accepted a 3 year post-doc (without telling me before hand). By the time he was finished, we had 2 kids with a 3rd on the way. He was supposed to work in academia so that I could go to school for free or at significantly reduced rates. He didn’t have his first job until he turned 30 and it wasn’t in academia. We couldn’t afford for me to go back to school and raise 3 kids.

    My divorce finalized 2 years ago.  I let him keep the house, the money in his personal checking account that he “hid” from me, and never asked for a dime from his 401k & pension. We share 50/50 custody and he complained daily for 2 weeks straight (I counted) about how unfair it was for him to pay me child support. It isn’t much, but in my state child support has very strict criteria and very little negotiating room. And he makes twice what I make.  

    Given my situation I could have “stuck it to him” if I wanted to. But that’s not me. If I hadn’t had the job experience I did or if I were a stay-at-home mom, then I absolutely would have taken alimony, but only enough to get me through college as we had agreed to early on. Once I had my degree, I wouldn’t want anything else to do with his money.

    So, not all women receive alimony. And of those eligible, not all of us take it. If your fear is women wanting you only for your money, then I think you need to change a few things. First, don’t flaunt what you have. If you normally drive a mercedes, buy a toyota for dates. Don’t wear expensive clothes or discuss finances when you are first getting to know one another. Don’t post your salary range in an on-line profile. When you tell women what you do, be honest, but general. If you are in finance, say that, but leave out the part about being at executive level.  On dates, keep it to “normal” stuff initially. Avoid 5 star-restaurants and yacht club events.  

    Second, pay attention to what she does and what she says. I’m not talking about the normal “listen to what a woman says” advice. I mean listen for hints about her motivation. If you are walking in the mall waiting for a movie to start, does she stop in front of a jewelry store to check out the merchandise? How often does she try and find out your salary or net worth? Does she seem fixated on brand name clothes/stores/cars? I think you can tell pretty early on what type of person she is, you just need to be open minded enough to see it and not jaded about how to interpret it.

    Good luck!

  19. 39

    I’m the OP and I’d like to thank Christa and the others for your great advice.

    I live near a resort/high-end vacation town so that explains why a   large number of the divorced women I meet have a upper middle-class lifestyle.   As far as the issue of permanent alimony goes, it is fairly common in my state for successful businessmen/professionals to pay alimony so the ex can maintain the standard of living he/she has become accustomed to.   Many states have limits on alimony now (Texas has a 3 year cap I believe).   Other states, such as MA, NJ, & FL, allow the judge to award permanent alimony.   Whether alimony in my situation was appropriate is irrelevant at this point.   It’s been ordered, I must pay.   If anyone is interested in learning more about alimony, a quick google search for “permanent alimony nightmare” will bring up quite a few hits.

    Regarding the women I find, I do not consciously or subconsciously seek out women living a life of leisure.   In fact I try my best to avoid them! However I might find a nurse, for example, on Match and then find out she had been married to an MD for years and now works one or two days a week.   

    One of my concerns is whether a woman would ever be willing to begin a serious LTR with me.   How many of the women reading this blog would be willing to begin a relationship knowing that your BF would have to forfeit alimony or a trust fund if he wanted to get married someday?

    The second concern is whether a second marriage could also end in disaster.   Evan said “But I’ll tell you the same thing I tell every woman who doesn’t trust: “The next woman has nothing to do with the last woman.” They’re independent rolls of the dice.”

    I agree 100% with Evan’s assessment if we were talking about an abusive partner or a cheating spouse, but divorce laws are not independent rolls of the dice.   When a marriage ends and an attorney tells her client that she is “entitled” to 50% of all assets and has a strong case for alimony, it is amazing how many people will say, okay, let’s go for it.   I have deep respect for women like Christa but unfortunately no one knows if their bf/gf will be a Christa or a Heather Mills 20 years down the road.

    For now, I will avoid the obvious gold diggers and also those receiving permanent alimony (who would have to forfeit alimony to re-marry).   That leaves a huge percentage of women that I can date and if/when things become serious, I can broach the prenup.

    I’m sure some readers will think I focus too much on the financial consequences but once bitten, twice shy is a pretty good motto.

    For all the readers, both male and female, you might want to seriously consider a pre-nup.   I spoke with a lady at work whose marriage ended after 20 years.   Both her and her ex had nice incomes until they decided to divorce.   She thought they’d split the assets down the middle, both would keep their individual pension plans, etc.   No – Ex went on disability, he took her to the cleaners and rec’d half of her pension while retaining his (disability pension not divisible per federal law).   A pre-nup would have protected her.

    Hmmm, maybe I’m going about this all wrong…. maybe I should be searching for rich women! 🙂  

  20. 40

    @ # 40

    Or maybe you should be searching for women who do not especially want to get married. Which come to think of it, might be those who receive lifetime alimony. Hmm.   So why is it   you don’t  want to date them again?

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