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. 41

    @ #40: “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”
    Here’s what worked for me and my X. I was the initiator. Except for a couple of years when I stayed home with the children, throughout our lives, we’d been making pretty much the same amounts. Because our marriage had always been kind of on the rocks, we’d kept our finances separate and split all family expenses down the middle. The only thing we had in both our names was the house. Before I told him I was leaving, I typed up a letter stating that we each have pretty much the same salary and savings, and therefore have no material possessions to fight over. I also said that, because it was my choice to leave, it’s only fair to give him the choice whether he wanted to stay in the house or move out. I’d be cool either way. I also added that I wouldn’t fight him for anything except custody, not even for child support (there’s only a couple of years left of it, anyway). Being a generally nice and fair guy (hey, there was a reason I chose to marry him back in the day…) he agreed that we should each keep our own, stayed in the house, and offered me child support and my share of the equity.
    However, in addition to all these nice offers and propositions, I also went out and hired the best, most aggressive lawyer in town. Cost more than the average price, I still miss that money… but that helped me feel that my back was covered in case my X would decide to try something. Kind of the “walk softly, carry a big stick” type of strategy.
    Anyway, my advice? Search for independent women. Personally, I’m more happier pinching pennies on my own income, than living the life of leisure while being dependent on somebody else. And I’ve been this way since my late teens/early 20’s, so probably not likely to change now 🙂
    @ Christa #39, yes this is exactly the situation I referred to earlier when I said in some cases, alimony is an absolutely just and fair thing. Sorry to hear things turned out this way for you. A family needs to be a team working together, and it upsets me greatly to hear about people that refuse to carry their own load in such a spectacular way 🙁

  2. 42

    Jaded asked: ” 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?”

    I would.

    Again, you’re assuming the woman you are interested in is only interested in you for your net worth.

    I earn my own money. I started babysitting when I was 11 and since then I’ve never not had a job.   What I’ve also never had, though, is a deeply loving relationship.  Money comes and goes. It pays the bills and is a means to enjoy life.  It does not, however, laugh with me, hug me or support me.
    I could keep expecting the next man I meet to take advantage of me, but I don’t. I’ve grown enough the past 5 years to understand why I married the man I did and why it wasn’t love I experienced. I also am well aware of the part I took in our dysfunctional relationship. Clearing out my own internal issues has made me a significantly happier person. I’m now excited to meet a man I can fall in love with. I view every date as an opportunity to have fun and meet someone new. If anything else happiness, great! If not, then I move on.  

    I’m not sure how to ask this without it sounding offensive, so I’ll preface it up-front by saying I’m really not trying to offend you at all. However, is it possible that you aren’t ready to move on? Or perhaps, you’re more concerned with losing more money than finding a loving woman? Again, I’m not judging or blaming, I’m simply trying to give you another thought to consider.

    I don’t know, it just seems like you of losing more money. I know I’m not the only woman out there that isn’t motivated by money. However, if you have a trust fund, then I’m assuming you grew up with money. So, my question is can you live without your trust fund? I think that until you can give an honest “no” as an answer, that fear of losing more money will continue to rule the way you date and view relationships.

    @ Goldie #42, Thanks, but don’t be sorry. It wasn’t all his fault. Short story – I had an alcoholic father and completely twisted views of what relationships/marriage was supposed to be. I was a great enabler, though! (eye roll). As I mentioned above, I am very aware of the part I played in our relationship. It wasn’t healthy for either of us. I’m a much better person now for having gone through it though. Plus I have 3 wonderful kids. So, no regrets!

  3. 43

    Christa @ 43 –
    I’m sorry if my question was confusing.   The point I was trying to make is that if I dated a woman who is receiving substantial alimony, at some point I could have my heart broken if I wanted to marry her and she would face the dilemma of either marrying me or continuing to receive alimony.   Likewise, I would imagine that most women would not get involved with a man knowing that he would face a dilemma (giving up   a trust fund, abdicating the throne to the UK, etc.) before he could marry.   Of course the bf/gf would hopefully sacrifice all to marry in the future but if you know the situation would that sway you from entering into the relationship.

  4. 44

    LOL….”abdicating the throne to the UK”?? Should I call you Charles or William?   😉   Sorry, that really made me laugh.  

    I understand your question. I know this is going to sound really trite, but I simply see it as irrelevant. And I suppose this is due to our obvious socio-economic differences. Let me address your concerns this way:

    Let’s say I was receiving alimony (and let’s say that the alimony is some ridiculous amount, like $5000/month) and also dating someone.  Part of the alimony agreement is that it ends if I marry. Now, let’s say that I fall in love with a man who proposes to me. Would I say yes?

    I really do believe in the innate goodness in people, so I believe I’m speaking on behalf of most decent women. The answer is: if I loved the man, absolutely, in a heart-beat.

    Money doesn’t make you happy. People make you happy (if you’re with the right ones).
    If I were dating someone who had money and he wanted me to sign a prenup, would I be offended? No. I would have no problem signing one and I honestly don’t understand why some women get seriously offended by this. As far as I’m concerned, any woman who is offended or refuses to sign one is only after your money and you should dump her immediately.

    Would I stop dating someone if they had to give up their trust fund (or throne) to marry me? No, but I think this is where we’re misunderstanding each other.        

    I probably have a very different view than the women in your social circles because I’ve never had a trust fund or grew up with large sums of money. Don’t get me wrong, I’m not living in a trailer park somewhere either! My credit is impeccable and my only debt is my mortgage, which is actually my  point.

    I don’t need a trust fund to live comfortably. However, because I’ve never had one, what is comfortable for me may be scraping by for you, and that’s the point I was trying to make.  As long as you have a job and can contribute to our cost of living, I couldn’t care less how much money you have or what I could have shared had you kept it.

    This is why I think it’s irrelevant to worry about how I would react to you losing your trust fund. I’m not marrying your wallet. I’m marrying the man who carries it. And any woman who doesn’t have that same attitude isn’t worth getting involved with.  

    As long as you can live with what you’d be giving up, then the woman should be equally supportive and happy.  Does that make sense?

  5. 45
    Karl R

    Jaded said: (#44)
    “I would imagine that most women would not get involved with a man knowing that he would face a dilemma (giving up   a trust fund, abdicating the throne to the UK, etc.) before he could marry.”

    Some women would.

    Jaded said: (#44)
    “if I dated a woman who is receiving substantial alimony, at some point I could have my heart broken if I wanted to marry her and she would face the dilemma of either marrying me or continuing to receive alimony.”

    You could also get your heart broken if she decides that she wants to reconcile with her ex. Or you could get your heart broken if she decides that she’s just not that into you. Or you could get your heart broken if she gets hit by a bus.

    Heartbreak comes with the territory.

    If you’re terrified of getting your heart broken, you won’t be able to forge a relationship with anyone, regardless of her prior marital status. Do you really want to let fear run your life?

    So go be a Wallis and find your Edward.

    1. 45.1

      “If you’re terrified of getting your heart broken, you won’t be able to forge a relationship with anyone, regardless of her prior marital status. Do you really want to let fear run your life?”
      Maybe one person’s caution is always another person’s fear. Who knows?

  6. 46

    I skimmed through comments and not sure if someone made this point already, but perhaps a good place to start for Jaded would be to realize that he’s made the bed he now has to lie in. The only way a woman would get alimony is if she was making substantially less, or never worked at all and lacks skills to maintain her lifestyle. Jaded chose to marry a non-career woman, he chose to have a housewife and probably encouraged her staying at home or not pursuing career goals. This disaster now is totally of his own making. Had he instead married an ambitious woman on a promising career track, he could’ve been receiving alimony now instead (which happened to some of my girlfriends – they paid alimony to their ex-husbands).

    So, as a proverbial “successful woman” who is seeing her male colleagues marrying actresses/waitresses and kindergarten teachers and dismissing women who are their equals, I wanna say – cry me a river, dude. Everything has its price in life, you want a granola-safe-the-earth-stay-at-home-go-to-yoga type – this will cost ya in a divorce court. Don’t want to pay that price? Go date women with brains and careers!

    1. 46.1

      Being a stay-at-home parent is a career, and one in which  either the mother or the father can be quite successful.   Thankfully you are not a family-court judge as you evidently devalue it.  And, kindergarten teachers arguably have  more patience and understanding of children’s development and an ability to teach them than hard-driving career women.

  7. 47

    I am getting divorced soon. My husband has spent many years holding it against me that his second wife got a big payout. She did not contribute much to the marriage but got half of everything. I on the other hand brought a lot into the marriage. I sold my house and cashed in an investment policy and put that money into the house. I also worked very hard in the family business for years whilst he took part time retirement and enjoyed his hobbies. I ended up ill with stress and exhaustion. His attitude to me has actually been the most destructive thing in our marriage and almost certainly led to it’s ending. Now we are getting divorced I have had to fight to get a fair share. Rather than be called a gold digger I almost agreed to walk away with only 1/3rd of the joint assets but my solicitor told me I deserved more based purely on my initial financial contribution. On being told I would get half the value of the house my husband said “I have paid for that house twice over and still get nothing”. Actually, in the time I have been with him I have doubled his assets after the split. I have doubled my assets too but done the lions share of the work in the marriage.
    If I ever marry again I will insist on a prenup to protect myself from any man who feels so hard done by. Even though I have been the main provider my husband still sees himself as the most important person in the marriage and always took the greater part of the income from the family business (a business which was virtually bankrupt when we met by the way). Why is it that men feel so entitled to a higher wage despite doing so little, both at work and at home. Interesting to note that despite only working part time he also felt entitled to not share in the housework or other normal family commitments
    As for lifetime alimony, I will get nothing. He gets the business back and can enjoy a good income since I made the business so successful but I have to find a new job, new home, new friends and start all over again at nearly 50 years old. By the way, he was the one who had the affair with a friend of mine because, as he put it, I was boring being ill and tired all the time and not paying him enough attention.

  8. 48

    “if I dated a woman who is receiving substantial alimony, at some point I could have my heart broken if I wanted to marry her and she would face the dilemma of either marrying me or continuing to receive alimony.”

    So live together and don’t get married. Big deal. Just avoid the alimony issue completely.

  9. 49

    Jaded hasn’t expanded on the situation and I think it’s stereotyping to assume simply because he has money, that he married below his station and “encouraged” her to stay-at-home. Even if that was the case, then I think she should be awarded enough to support herself while gets an education and then finds a job. I think lifetime alimony is excessive because it does nothing but enable a woman to be dependent on someone else or gives a lazy person an excuse not to work.  

    I also had to ruefully smile at your stereo-typing stay-at-home moms. I’m a “granola” person (been a vegan for 6 years), a lifetime member of the sierra club, drive a hybrid, and enjoy yoga and tai-chi. I also own my own company (tech related, not “granola”) and fully support myself. I think I kinda break your mold.   😉

  10. 50


    I am not stereotyping, I am thinking  about this situation logically.  No court in no state would give life alimony to a woman who makes equal $$ as her husband, in fact, to get life alimony one should be married for quite a long time and make substantially less than their spouse.  Also, Jaded doesn’t really have money – as he says he can’t retire, so he’s not wealthy but most likely  upper middle class.

    As a career woman, I firmly support  alimony for stay at home wives. Men drawn to “nurturing” types should know that these women will have financial consequences. In this case at least some of them consider actually forming a “power couple”. If men know that they can marry a non-career woman and kick her out whenever they want at no cost  – then they would have no incentive to try to deal with their equals (which is intrinsically more difficult). This levels the dating playing field for me great deal (speaking from experience). I understand this sounds screwed up somewhat, but that’s the world we live in.

    And yes, my “granola” stereotype was mostly intended to portray a soft, nurturing type as opposed to type-A type, I don’t have anything against vegans or yoga per se though don’t find much use for either.

  11. 51
    Christie Hartman

    Jaded #40: “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.”
    I too respect Christa – but not for the reason you do, Jaded. I respect her good attitude, given an unfair divorce settlement. This example shows that for every Gold Digger who wants excessive alimony, there’s a selfish jerk looking to keep everything he supposedly “earned” while his wife sacrificed her own education for his. Christa put aside a lot for a LONG time – I know what it’s like to go to college, then to grad school for another 4 years, then do a 3-year post-doc. And if my partner had sacrificed his career while I did all that, you can sure as freakin’ HELL that I would pay him back for that in some way, whether we divorced or not. This is just human decency.
    There’s a big range between Christa and Heather Mills, dude. The problem here isn’t women – it’s your attitude.
    Stacy #47: I agree 100% that “everything has its price” and that men who want stay-at-home moms need to pay for them. But your comment that if men want to avoid that they should “date women with brains and careers” is pretty insulting. Last time I checked, kindergarten teachers have brains AND a career, and yoga-lovers (and even stay-at-home moms) have have brains. This is a tough pill for some “career” women to swallow, but a LOT of people want children, and SOMEONE has to care for them, which often means sacrificing some aspects of career. Most of the time, the woman makes that sacrifice.

  12. 52

    Well said Christa. I was one of those housewives awarded permanent lifetime alimony. I was a stay at home mom for 21 years. I am college educated and have 3 children. I tried to work part time but, my ex worked the second shift. I worked eight hours a day and then had to come home and care for my 3 children alone during the most crucial hours of the day. I choose to stay home rather than lose my mind! To think women awarded lifetime alimony are sitting around leading a life of leisure is extremely insulting. Most times the alimony pays for very little and the ex wife NEEDS to get a job.   My ex was abusive and I stayed many more years than I had to because I knew I could not support 3 children on my own. I started looking for work after the recession started and could not find a job.  
    Alimony does not have any  consequences  if it is not paid unless you take the ex to court. What woman with little money can afford a lawyer and do that? I paid a lawyer 2000.00 to get an 8000.00 lump sum in alimony and signed a paper saying he did not owe me anymore money. In the end I have lost my house and all my financial holdings. I am now filing for  bankruptcy. My ex, because of his work history, is now in one of the top jobs he has always coveted. So quite whining about all these woman lounging around with lifetime alimony! Get over it! I have been thru hell and back and still believe in a loving marriage for my future. We all get burned by life. I am so  tired  of meeting men who have been so “hurt” and taken of financially by the woman in their life. They are so bitter that they never want to get married again. Yes, they want everything else but the commitment. Put on your big boy pants and deal with the hurt. We all have to quit whining about our bitterness and get on with a hopefully a better life.

  13. 53

    Jaded, it sounds to me  as if you are still carrying resentment about paying the alimony, and that you are  challenged by  this  reality of your previous relationship.   To me that is the first hurdle to overcome, and it’s an internal, not external, process.   I agree whole-heartedly with EMK on this one – each new potential GF is a brand new person, much like each new child born into a family from the same parents is so different to parent.   While there are practical considerations as you can’t move forward with your original plan (like so many of us divorced with shattered happily-ever-afters), that to me sounds like it could be the second part of your resentment.   You enter any kind of new relationship with this burden on your heart, and it skews how you look at any potential relationship, before you even know the woman or her intentions!   As I read all the responses above, there is no one-size-fits-all, which is why I respectfully suggest it is an internal mind-set.   Your life has been altered financially, no doubt; but will it define you for the future?   Background:   I am a divorced 54 yo with 3 now late teens, married for 24 yrs, SAHM for 10 yrs,  but college educated.   When the relationship went sour (he was financially irresponsible and wiped us out), I had to redefine myself, too.   Now am working 2 jobs,  and am receiving spotty child support (he has trouble keeping a job)  and $100/mo alimony until my youngest is 18.   Yes, I resented his breaking his promise to take care of us.   But his actions don’t define me.   I define myself now that I have new circumstances to contend with.  

    To my utter amazement, men of means that I am dating simply don’t care about any of this.   They are watching how I have handled this devastation, recovered, and the fact  that I accepted my own reality and am not resentful and am not looking for  support from a future mate.   I’m also happy despite it all – took lots of internal work to get there.   Would I dump  (rare) lifetime alimony for the right guy and sign a pre-nup?   In a heartbeat.    Ironically, the one who has my heart right now is a CFO!   My long-winded point is this;  my dates  are looking at how I have handled the cards I’ve been dealt.  They are all divorced,  professional, upper middle-class men paying support of some sort.  That’s the bigger issue to them  than how much $$ I have or don’t.   It speaks to our character and where you are in your recovery…what you value and what you are doing about it, despite a big setback.   You sound like a really nice person who’s still smarting, and rightly so.   But where to from here…in your mindset?

  14. 54

    What Stacy said.

  15. 55

    Christie Hartman #52, I agree 100% with everything you said. I’d only add one thing:
    When a couple has been married for a substantial number of years, it doesn’t always make sense to keep score of who owes whom what. BOTH partners sacrifice a lot for each other. It’s easy for me to remember every sacrifice I made for hubby; perhaps a little less easy to remember, or even know, every sacrifice he made for me.
    If one person feels that s/he is making inordinate amounts of sacrifice, or somehow didn’t get the chance to pursue a dream because of the spouse, then the couple should discuss it. Not keep on sacrificing with one’s mouth shut – because resentment builds as a result, and that poisons a relationship. It’s possible that the spouse wasn’t even aware of the sacrifice being made: not out of malice, just cluelessness.
    As for Jaded: I can’t improve on what Evan advised. I would just second the commenters who suggested that you deal with the resentment first (maybe by setting up that separate bank account whose alimony payments you never have to see). Then approach dating with a fresh mind, and consider that you needn’t marry again to be close to someone – LTRs without marriage certainly exist.

  16. 57

    I can really identify with this person. I don’t know what is wrong with the alimony laws in most states. They are certainly geared against men. I was married for 22 years to a physician who stayed home for 5 years to raise our two kids. She had an affair….filed for divorce, and demanded lifetime alimony. She said she didn’t want to work anymore and wanted to stay at home for our kids. Both are in school full time. Long story short, she got 70% of the assets ain’t return for me being on the hook for a 6 figure annual alimony for 10 years. The court system is really rigged against men in most states, but I would advise not holding that against anyone you may date. Just insist on an ironclad prenup if it ever reaches that point. I’m still bitter 2 years later.  

  17. 58

    “How Do I Date After My Divorce If I Think All Women Are Gold Diggers?”
    With great difficulty, considering you’ve been severely burned already. DON’T DO IT!!!

  18. 59

    Know this: It is your right to expect that a man will pay for your dinner, your movie ticket your club entry fee, or whatever else he has to pay for in exchange for your time. – Steve Harvey

    Comments like this from Steve Harvey (and the fact that a woman posted it and obviously believes it) do nothing to change my jaded opinions after divorce… There is an old joke that applies here… A man walks in to a bar and sits down next to an attractive woman. After a bit of small talk, he looks her in the eye and asks “would you have sex with me for a million dollars?” She considers for a moment and replies “why yes I would.”   The man quickly comes back with “would you have sex with me for 100 dollars?” The woman, acting hurt, says “What do you think I am? A whore?” The man laughs…”We’ve already established that – now I’m just negotiating!”
    Now obviously I know not all women fit into this stereotype… but lets be honest. There are a lot that have serious, serious entitlement mentality based on having female genitalia….

  19. 60

    Nowadays, women can get ripped off in divorce settlements too.   And how do I know that?
    You date and perhaps avoid wearing expensive clothes (you know the type) and try and look like everyone else.
    If she’s a golddigger (or even he is), there are things they will ask you right at the beginning.   Don’t believe me? Here are some examples I’ve heard (even from rich men):   How much do you earn (date one), do you have a fixed employment contract (date one), do you own property (date one), which car do you own (ha!), how much do you pay for your (clothing, perfume, etc.)? These questions already show you a tendency to be interested in your income, don’t they?
    You don’t have to get married again.   Or…if you really wanted to, make sure there was a contract in it (signed while you are both starry eyed) to say that what belongs to you, belongs to you and your descendants.
    If that doesn’t work where you live, find out what does.  
    I’m not bitter about being ripped off, just wiser.   And will make sure that what belongs to me and my descendants will stay there.

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