Dear Matchmaker Rabbi:

I have been dating a woman for a few months now. I’m a substitute teacher seeking a full time job. I also work as a pet sitter and in a retail store part time. I barely make $30,000 a year. She is a pharmaceutical rep for 25 years making at least six figures. She thought she could get past my wages and not having my own place, but it eats her up inside. She is afraid she has fallen for me, and I have fallen for her. Now she is asking to just be friends.

What can I do but tell her I will work as many jobs as I can!? I know she is the ONE, but she can’t let herself close because she thinks I may not have good intentions — in other words, I’m after her money. Secondly, if we get any closer, she is afraid that I could never catch up to her finances and be an equal partner.

My true intentions are to want to be with her, not to need anything from her. I have fallen for her deeply, but she will not let herself do that with me. Since when is money a big issue in life? I guess I’m old fashioned and thought it was the person inside, not the wealth, that mattered. What can I do?

— Sheldon

Dear Sheldon:

Since when has money been a big issue in life? Since forever. Most marriages for most of human history have been family arrangements negotiated to gain a family’s financial or political standing. We are, thank G-d, moving past these ideas in the United States, but old habits and old ways of thinking die hard.

What you can do is stand tall and be proud of who you are and the good work you do in the world. Putting in an honest day’s work, and doing the best you can at your job, are the criteria by which your beshert (your intended one) should measure you. If this special lady is not able to do that, she is not your beshert.

I hope you never promise to “catch up” to her finances because as a teacher vs. a pharmaceutical rep, you never will. And there shouldn’t be any shame in that, either. Why is your respective worth based on the size of your paycheck, anyway? Change the yard stick and you change the outcome. If the comparison were “Who is making a more positive influence in society,” – I would say you win, in spades.

If your date is really is so concerned that you are just “after her money” – get one of those nifty-difty things called a prenup. Offer to sign one. And be sure you have your own, independent legal counsel looking it over before you do.

— The Matchmaker Rabbi

To ask the Matchmaker Rabbi a question, email her at

Joysa Winter, aka The Matchmaker Rabbi, knows all about how hard it is to find lasting love. It took her 17 years to find Mr. Not Wrong! In that time, she tried just about every singles site, dating club and Matzah Ball known to humanity. Now a rabbinical student and the mother of 2 young kids, nothing brings her greater joy than officiating a wedding. She is finishing a book on her dating misadventures called Chasing Cupid, Tales of Dating Disaster in Jewish Suburbia. Read more about it at
  1. If she is concerned that you do not make enough money, that is her problem. And whatever you do, you can not solve it for her. It seems like you are trying to find a way to solve the problem, but only she can change the way that she feels about this.

  2. These people are right. One thing about human thinking and behavior at the moment is the sum of all her experiences. She is seeing a past situation happening at the same time she is with you. Basically she has not dealt with the hurt of past experiences. So now she is on guard and if anything even “smalls” like the past her red flags go up and she pulls away. Get to the bottom of this problem before giving up. Ask questions and find out what’s really fueling this fear of hers. In just a couple of answers you will be able to tell if it’s fear of being used or she is just financially focused. Explain the best way you can that teachers will not make as much ever but this is your passion and your dream. A pre-nup is a sticky situation but through it in with your reasoning and listen to her fears without trying to solve them. Then you can tell if it is her, or someone else talking. Maybe her mom or family or friend is pressuring her to walk away from you. Whatever the reason you should at least get an answer before making your own informed decision. Remind he of why you fell in love with her and what makes you crazy over her.(be specific about what it is that makes you crazy for her) Then at the end you will see how much work it takes for two humans in this world to make a marriage work. She will either be willing to work at it or not. Sometimes we find Kindred spirits that we feel the same love for as Soul Mates but there is a difference.

  3. move on ….let her come back to you…if she comes back…fine… if not she is not for you anyway…if your intenions are honorable you should be able to move on easily enough.

  4. Hi Guys,

    This is a hard one! I am a pharma rep and all i can say is….it would be hard to be with a guy that has substantially less money. A little less is okay….it just makes a difference, whether we like it or not. How we wpend our money etc etc….eating out…with a guy that is just have to watch every dime.
    Having said that……money isn’t everything. (its alot). But not everything.
    If you put the oney together, you could make life alot more fun….its good to have a companion…but…as the above said…there are different deal breakers…thats seems like one of’em fr her…shame……and to the guy…don’t change who u r for anyone….neither of you should…..Sassy

  5. To Sheldon,

    Any woman who is that consumed with what you make is not worth getting involved with as even if there is a marriage, misery and divorce is a high probability. Most teachers nowadays are in a union and are highly compensated. Actually their real compensation is in the upper 3% in the nation. The teacher unions try to fool the public into thinking otherwise. Just look at the obscene school taxes. They only work 8 months a year and get 12 months pay. And many get high paying jobs for the summer in the school system or related areas. And the free non taxable fringe benefits equal (full health coverage,, etc) the yearly pay. You will be making far more then your pharmaceutical rep girlfriend who’s pay is on commission and fluctuates. And we are in a recession, so her pay is down now. She probably is inflating substantially her pay to impress you. Also she is not in a union and with the horrid economy could be fired. I recommend you step back and then have a serious talk with her. Any one who puts money as a priority in a relationship is trouble.

  6. I don’t blame her one bit. As a divorce lawyer, I can say that the majority of divorces that I handle are the result of cheating. The second biggest reason is money. When one person makes significantly more than the other…it is a problem. It is a big problem. This problem seems to be magnified when it is the wife that makes significantly more than the husband. This is due to many factors. One, our society views a wife’s income as disposable – meaning that if wife lost her job, husband’s income should be able to cover most, if not all, of the family expenses. Two, psycholgocial reasons. Many men would feel less like a “man” if his wife were making a lot more money.

    These reasons may seem crappy, but make no mistake, they are very real. She shouldn’t have dated him in the first place. There are plenty of guys out there making 6 figures.

  7. I can empathize with this persons’ case. However, how many generations of humanity were married with the entirety of a household on a man’s finances? Now that women have had the opportunity to join the work force and make their own lives, money and goals, they are doing what men did to them (or their families) in not accepting a mate (or ‘the one’) for how much they make.
    Give someone an inch, they’ll take the whole tape measure!

  8. Time to move on. She’ll never be satisfied and will end up resenting you. Take it from one who knows.

  9. The whole conversation is not as it should be. People should be forging partnerships. One never knows what may happen in life. You may be doing well. You may get a full time job. She may lose her job. You both could be doing well. You both could be doing crappy. You find ways to live and laugh no matter what the circumstances are. That is what love is all about. One never knows what health issues may arise. Or other circumstances that may enter the picture. Create beautiful memories. Face the up’s and down’s together. That is what love is all about.
    This is not a competition!

  10. Nothing has been said about children. A woman who wants to stay home with children may need a man who can support the family on his own.

  11. I was involved with a pensioner who lived on the pension rented an apartment had no assets to speak of, a very old car, and not much in the bank which he couldnt touch till he was a certain age. i have substantially more and a job yet he wanted me to give up my job sell my house move to the overseas country he live in and share all my funds and be in control of it and tell me what we can afford to spend or not, combine his and mine… it was his idea. i loved him so very very much an still do and he tried to convince me that he was not after my money and when he inherits as he will i will be part of it. i felt very insecure as in the past my ex husband and i shared an account and i was always the main income earner and we had to financially support his two children for eight years even when he was out of work, it fell on me, so i lost quite a bit of money through that an a bad investment. unfortunately i now have lost the love of my life due to my insecurity about money but fortunately i still have my funds to myself. i sometimes wonder if i did the right thing an how important it would have been to have rather been with the man i loved and shared my funds or now alone and missing him. any comments?

  12. move on. with all the good looking young teachers out there what in the world are you doing with a pill peddler anyway? kidding aside, stick with your own kind, you’ll live and love longer. good luck, take two, and DON’T call her in the morning!

  13. Consider her profession and these in it…. If what you do reflects on who you are, you may be better off looking for someone else. These that excuse the money principle have no idea what love and life is about. Remember – you can not take it with you when you die and in life love can not be bought. The newest toys will never replace a relationship. Money can change one’s life and not for the better. People atrophy inside.

  14. This maybe the “ONE” to stay away from. She has you Doubting your “Worth” as a person,just because she has “FEAR” of your Income being lower than her own. This Cannot Be THE ONLY THING wrong with the Idea of you and she being a couple, and those things would come out LATER and have everything to do with THIS SAME FEAR….Of you and she and a FUTURE TOGATHER. Move On To NEW places to meet DATE-ABLE/ Relationship Interested Woman, Like My own favorite place….Take a CLASS in some kind of Subject YOU are INTERESTED In (Meetings no more than 1 time a Week). Thanks RAB I.

  15. My first response was to Sheldon but this is to the “matchmaker”:

    “I hope you never promise to “catch up” to her finances because as a teacher vs. a pharmaceutical rep, you never will.”———

    I was married to a Union Teacher and her compensation was over $100,000 a year! Cops and School Teacher have the MOST free non taxable benefits of any profession with the least amount of actual work time. Pharmaceutical Reps have no union and work on commissions and when things are bad get fired. NOT SO in a Teachers Union Job, so I suggest before giving advise you check out the facts first and NOT rely on Teacher Union propaganda!

  16. It sounds to me like you’ve been spared. It hurts, I’m sure, but down the line her honesty and authenticty now will save you a tremendous amount of grief and suffering. Holding on to the belief that she’ll change her mind because you love her so much (now) is attachment and will ultimately end in suffering.

    I wish having equal financial assets wasn’t a “problem”, but it is for her. Obviously, you wish it were not a factor. In this situation I would ask myself or, you, on what planet does an inequitable financial position ultimately not end up with resentment? In reality, not this one. But only in Reality.

  17. Sheldon, I agree about it’s better that she told you now. Get out my friend. She is not for you. You would end like a puppy dog chasing its owner all the time – NOT GOOD!

    Separate subject: I don’t understand the women who don’t even bother to open messages – blows my mind! They don’t even care to know what I have to say? All the best to all G’mar chatima tovah. I got out of my sick bed to check mail and I’m going back to bed …. David

  18. I feel I have to shine in here. My degree is in business, and I am in the accounting field; though I counsel my peers on different subjects as it relates to dating and meeting, and all other issues that arise. Today we live in a very complex world. Some of the most successful business people have had trouble directing their own children as far as what direction to go. There are no guarantees in this world. Trust me on that. Yes, sales people can do well, and also can do poorly. If you have the determination to do well, that is the most important thing. I know someone very well on jdate who doesn’t have to work a day in his life. His net worth puts him in the top 1% in the country. He also has difficulties meeting, and is not a show off. He laughs when women wanna know how much money he makes, and what health insurance plan he has. It is all the way we are brought up. To the substitute teacher here feeling this pharma rep, may not wanna stay with you; you need to stay focused and not feel vulnerable to what someone else does or has. You have your own skill sets, and are your own individual. If your last name was Steinbrenner would you still feel bothered by how much this young lady makes? Economic issues are too often used in the jewish community, to create feelings of insecurity. Is money important? Of course. Is it everything? Of course not. Some think what makes one successful in life is marriage and children. Many don’t realize that these young couples who get married out of college often have big time help from parents. There are many couples married a long time who do not have a big savings. Don’t go by where one necessarily lives or the car they drive. Leasing today can make anyone look rich. There are people on the north shore of Long Island who have Trump’s resources who intermarry because they don’t want to deal with the issues that you are describing. You should only have success in your future and good health.

  19. In reply to David regarding women who don’t read emails. That’s why I send flirts. It’s fast, easy, and less disappointing. If women are not paid members, they cannot open written emails. I think they can read flirts, not being a paid member. In any case they have to be paid members to write back. You can try iming them, as they can receive an instant message even if they are not paid members; they just can’t initiate one. Women often reject my ims. I never thought I was ugly; as I always got compliments throughout my life. I don’t think many women on jdate know what they want. I myself meet women a decade older who are nicer. However the prospects of having kids are decreased. Jdate has had some success stories. However it seems the one’s I know are the same people for the last decade plus on the site.

  20. Move on. No run on. You’ll be sad for a while, but there is an old Spanish saying, “We money goes out the window, love soon follows”.Keep looking, and don’t look back.

  21. I think there are 3 components to a great relationship. Trust, Respect, Shared life experiences and Attraction. Unfortunately if you don’t respect your partner because he makes less money than you, the attraction will fade and you won’t be able to sustain a healthy relationship.

    I admire her for her honesty and I know given that I have achieved a certain level of success in my life, I’m looking for a life partner, not someone I think I will need to support and take care of.

    The best matches are people who are partners in love, life and where they are in their careers as well. Once you become parents, then the roles shift but you have to start out trusting and respecting each other.

  22. Sheldon

    Most people in the UK are finding things tough than they were a few years ago

    Your Girlfriends comments to refer to previous times
    ask to see her sales figures from that ere and her present numbers

    If she cannot accept you for what you are its time to move on

    I find it marvelous that you are working hard and have more than one job

    Theres a million women on jdate obiously shes not the special one its time to move on

    Good luck

    Theres a saying “plenty more fish”

  23. It’s simple, if she really likes you then money won’t matter but it seems as though she’s a gold digger so I’d say it’s time to move on.

  24. She is absolutely correct to move on from the relationship and stay friends. If she cannot accept his inability or unwillingness to earn a decent living – while she does, this will continue to be a point of contention in their relationship. As individuals seeking an appropriate long term partner, we each have the right to prioritize our needs and if finding a financially stable or higher wage earner is important – then neither party should settle for less. This does not and should not reflect negatively on either party’s character, morals or ethics – and no one has the right to claim that it does.

  25. Hi – I am everything a man could want

    outgoing witty warm caring fun educated athletic confident musician
    professional mentally and financially stable
    been on every website, dated lots of men – gone to many single weekends

    but I just cant find the one

    I feel its because perhaps ment feel intimidated by me and my accomplishments – they dont want to travel to date – they are commitment phobics – they are not mentally and financially stable

    what should i do ?

  26. My ex-wife, who is on nice 6 figures, has been seeing a guy who is on roughly half that, and unlike her has no assetts at all, and still pays alimonys to his ex and 2 kiddies.
    He was very understanding when she offerred for him to move in with her under some strict conditions. She even got everything done in writing by a lawyer and signed by both in front of witnesses that he will never have any claim on her assetts or income whatsoever if the s–t hits the fan and they decide to part ways. Now he has got his life in order, she made sure he is up to date with his taxes and child support and now has confidence in building up his income.

    You have to understand that for women the financial security is very important and having a partner who is on 30k a year means either he lacks ambition, lacks self confidence, or is a schlimazel. With all these scenarios you are unattractive as a life partner. You may be the nicest guy in the world, the hottest dude in bed, or the greatest do-gooder but it does not insure financial security!

  27. My advice? Write her a verse:

    “How does it feel
    To be on your own
    Like a complete unknown
    Like a Rolling Stone”

    Then leave.

  28. If she says she wants to be friends, regardless of the reason, you have got to respect that. Be friends or not, but don’t sell yourself because you are obviously not what she wants.

  29. I’m just starting to deal with something like this myself and very nervous. I’m just a bit under 60. My wife got us in a tremendous amount of debt, we lost our house and had to claim bankruptcy. We’re separated, but I’ve got pretty much nothing left for retirement and have two kids ready to enter college. I’m renting a house, helping to support my wife, her rental and 2 of my 3 kids who are under 18.

    I’m just (this week) trying to get back into meeting people and I’m pretty nervous about the financial situation. Yes, I do have to watch my pennies. I do earn just over 6 figures, but taking care of two households and two kids just isn’t easy. Without being able to use itemized deductions, it’s even worse for taxes. So I’m trying to save what I can. I’m not interested in jumping right back into a long term relationship but I will want one eventually. Isn’t a woman going to be turned off knowing the guy doesn’t have any kind of retirement nest egg?


  30. Dear Sheldon,
    It has nothing to do with money but more to do with the fact that she is driven and you ate not!
    You are completely different people at the core. Your views on life are different, quite different. You are happy pet sitting and she could never respect and love a man who is happy being just that.
    I am guessing you are quite laid back while she is a go getter!
    If she had feelings for you, she would never use the word “friend”
    Move on now!!!

  31. Even if financial disparity wasn’t an issue in the beginning, it certainly will create resentment in the future. The biggest killer of any relationship is feeling contempt. Sheldon, what you do and earn is your business and you shouldn’t change to fit in anyone’s standards and expectations. And as hard as it can be, the best decision would be to just move on. That is what I would do in your shoes.
    Sorry, painful decision ahead.

  32. A wise, although annoying person once told me the only true prenup is when both parties have economic parity! Relationships work best when there is economic and looks compatibility… IE always date within plus or minus one. If 1 is ugly, 10 is a supermodel, and 5 is an average bear, a 5 should date between a 4-6. Anyway, looks like you guys aren’t economically compatible so bail!

    Now I just have to find a girl that makes as much as me! I am going to be single forever! LOL

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