Where Do You Draw The Line When Your Girlfriend Asks For Money?

boyfriend giving money to his girlfriend

Hi Evan,

I’ve been reading your blog weekly for almost 6 months, and have been many of your past archives. I’ve not seen this question answered before, so here goes: Where do you draw the line when your girlfriend asks for money? We’ve enjoyed each other immensely for the last 9 months… until she decided to return to school to get an advanced degree. She now can only work part-time, and has trouble paying her bills. On top of that, her car recently died and she had no money to get another one. I gave her some money to help her get a used car, but she still struggles to pay her ($1,000 per month) mortgage and other bills. She says that since she would do anything for me if I had problems, she expects her man to do likewise for her. I have a decent job (making about 100K per year), but I just don’t like the idea of giving anyone money. We appear to be breaking up over this, since she says she really can’t stand the thought of her man not helping her out if he can afford to do so. Am I wrong?


Dear Bob,

Congratulations. You’re her sugar daddy.

As I see it, the real problem here is that you bailed her out without having a commitment – and now she feels entitled to more bailout money. You’re the U.S. Government, she’s AIG – and your relationship is still ill-defined.

She’s relying on you as a husband even though you’re not a husband. Which makes this a good time to ask yourself: do I want to marry this woman

And, if not, breaking up might not be the worst thing in the world.

As I see it, the real problem here is that you bailed her out without having a commitment – and now she feels entitled to more bailout money. You’re the U.S. Government, she’s AIG – and your relationship is still ill-defined.

That ill-defined relationship – 9 good months together without living together or getting engaged – seems to have created a blurry set of expectations on her part. She genuinely thinks that your money is her money and is depending on you to carry her while she tries to work and go to school simultaneously.

And unless you agreed to that arrangement, you’re allowing yourself to be used by her. It’s really easy for her to say that she’d do anything for you – in theory, I’m sure she would. But what if you decided you were going to quit your six-figure job to be supported by her as you attend art school. And to supplement that, you asked for an allowance, because affording rent, tuition and supplies was suddenly cost-prohibitive? I’ll bet she’d be singing a different tune.

The rules do change when you’re living together, engaged, or married. If I’m paying $3000/month rent and my fiance lives in my room and can’t afford to contribute much to our monthly expenses, that’s fine.

If her car gets dinged and she’s too cash-poor to fix it, I’ll offer a loan, which she may or may not repay.

Hell, this year, my wife underdeclared her taxes and I had to spend a decent chunk of change to make it right with the IRS. Was I thrilled? No. But that’s the sacrifice of marriage. That’s what you do in a partnership.

The bigger issue, Bob, is this: the RIGHT woman doesn’t WANT you to bail her out. The right woman wouldn’t ASK you to subsidize her education and strain your finances.

Think about what would happen if you were to break up with her. Would she be homeless? Would she have to quit school? Would she have to get a different job? Would she have to move to a cheaper place? Whatever it is, she is fully responsible for herself. And by taking responsibility for HER lack of finances, you are the enabler who allows this to continue…and then you resent her for it.

The RIGHT woman doesn’t WANT you to bail her out. The right woman wouldn’t ASK you to subsidize her education and strain your finances.

If you think this woman is your future wife, then perhaps this is a sacrifice that you want to make on her behalf. But if she’s not, I’d put a stop to it right this second.

So, in answer to your question: “Am I wrong?”: if you’re wrong about anything, it’s in being TOO generous with a woman who is perfectly content in exploiting your generosity.

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  1. 41

    I was just thinking about something similar.. It often happens with me that I make a friend, we become good friends in a few months time and then that friend gets into some trouble. Whether its lending him money or getting buying something fro them because they can not afford it.

    And the part i hate is as soon as they’ve got their help they just vanish!!! They never call or text!! Its so makes me feel so bad… Now i don’t lend money to my friends unless i know this is a person who just can’t sleep untill he’d pay me back.

  2. 42

    Just for fun…since we enjoy speculating on the motives of people we don’t, and never will know…let’s try this possible scenario on for size:

    Bob and gf meet either through online or not with the self stated goal of wanting a “LTR”. They hit it off. They really enjoy each others’ company as Bob puts it, and here and there the subject of possible marriage and children in the future comes up. Gf would like to get an advanced degree before starting a family. Reason being, it would benefit the family later on in terms of financial security.

    Bob’s all for it. He likes a woman with a higher level of education, not to mention possible higher earning capacity. Yes, this is ideal future wife and mother of his children material. So, Gf goes for it, knowing it will be tight only working part-time, but thinks she can swing it. And 100k a year Bob, could help smooth any rough edges since they share the same goals, right? She’s not just doing this for HER, she’s doing it for THEIR future.

    Uh…maybe not right. After helping her out with some bills and a clunker car, Bob is reasserting his position as someone who doesn’t like to give other people money. And seeks validation on that front. Bob’s Gf is becomming dismayed by this “new?” attitude and wondering if Bob is in fact like that husband in “The Joy Luck Club”; and perhaps she made a mistake thinking they were on the same page as far as commitment to a future together.

    Just an alternative scenario to the “Golddigger seeks Sugardaddy” one that has already been amply represented.

    1. 42.1

      This is great and exactly along the lines of what I was thinking. Perhaps Bob isn’t investing in her as much as he should or as much as he first portrayed he was willing to do. We are only hearing one side of the story and he’s got a confirmation bias surely looking for evidence that he’s the “right” one in this matter. The issue that I have is that she (girlfriend) is “expectant” as tho it were owed to her. This would be akin to a man expecting sex. I personally would have gone about this differently and not EXPECTED BF to pay, but simply let him know how hard things were going for me financially and watched to see if he stepped up. If he didn’t this would give me clear indication of the type of person he was and I’d be asking if I wanted to be with this type of man any longer. I would prob then pull back myself, and when/if he asked what was wrong, I’d tell him how stressed I was with school/financial obligations. He can then choose to step up and help or he can choose not to, but it is then up to me to make a decision. Perhaps then I would call it quits or tell him I needed a break and start dating others. In this scenario, both parties are not being asked/expected to do anything, they are not putting expectations on another. Bob could then decide whether she was important enough to him to step up. In my opinion, if a man really loves a woman and can help financially to relieve her of her burdens then he will. This is best achieved via free choice and not bc of expectation or demand.

      1. 42.1.1

        What if its the other way around though? No girl would give a penny to a guy.

        1. Aaron

          That’s not necessarily true. In response to 42.1.1

          My ex wife hit a hard patch when the economy in Europe tanked in 2012. I helped support her for about a year even when she wasn’t my wife at first, but she was very frugal and I didn’t have much to send because I had many of my own bills to pay. I trusted her fully and knew she wasn’t blowing it.

          Later when I left my career making $55k to go to school for a new one, she helped me out. I now make $200+k per year. We ended up going our own ways, but the thing is that she was very trustworthy and showed no signs of gold digging.

          If your partner likes you to or always asks you to buy her stuff, plus asks for money, alarm bells should be going off. My ex wife would be in shock if I wasted money, but I’ve had a partner that wanted extravagance. She was the pay to play type.

    2. 42.2

      Right, but the decisions you make in life are your decisions.   Her choices, her debt.   Your scenario sounds like she has expectations of him that he is completely unaware of.   Once again, I love the statement by someone else that it is easy to say you would do anything for someone, talk is cheap.   Sure, she is getting the education for “THEIR” future, but it could just as easily be for her future alone since they aren’t married.   So I think this goes along with the talk is cheap statement.

  3. 43

    What stood out to me was “expects her man” part of the letter. I know we are only hearing Bob’s side and don’t get to hear hers but when I hear women use the phrase “my man” it is usually in the context of “my man had better be taking care of me” kind of thing – you know, with the attitude of “I’m all that and he better be down on his knees grateful to be my man”. I know – a lot to get from three little words. I’ve always found that attitude a litte repulsive and wonder what the guy found attractive.

    The other thing that rubbed me the wrong way was his phrase of “enjoyed each other immensely”. Not enjoy spending time together, not love being in each others company, not have a great time together – sounds to me like his involvement in this “relationship” is strictly physical.

    Just my thoughts.

  4. 44

    I don’t get why you are telling this scenario here.. :-/

  5. 45
    Mikko Kemppe

    I really like the way Selena presented her view of the possible scenario, and how it gives this whole conversation a more positive alternative to the story presented. Thanks for sharing it.

    Mikko Kemppe´s last blog post…Do Men Just Want Sex? Should My Decision Be To Wait Or Not To Wait?

  6. 46

    @ Honey:
    I’ve always told people that a house is not an investment because no matter how much your home appreciates in value, if you wish to sell it you must move somewhere cheaper and/or smaller in order to realize any profit. Otherwise, to maintain the same standard of housing you are going to have to pay about the same amount as you sold your house for.

    It sounds to me like Bob is tired of being considered the Bank of Bob. There’s no reason he should have any responsibility for her expenses. This woman has a mortgage . Didn’t she make any kind of plans for paying that before she quit her job to go back to school? Was the Bank of Bob her plan?

    Perhaps she ought to get a roommate to help with the mortgage (see Evan’s other recent thread about dating the unemployed)…

  7. 47

    Sorry, I disagree with Evan.
    If you love someone, you help that person – if that person doesn’t repay, you get rid of that person cheaply, instead of spending my whole life on someone who is not dependable.
    And I have put my mouth where my money is – I loaned some 2500 dollars to a friend couple of times.. he paid it back – if he hadn’t it would have hurt, but I was willing to risk it – because I trusted him. Even if it was my only savings, I still did that, and I didn’t regret it.

    Likewise I expect a man I am with to help me – if he doesn’t, he can get out of my life since he just wants the good things that come with knowing me.

    Money is just money, important only when you don’t have it.

    I would say to the girl that “get rid of that scroodge, he is using you, he isn’t ever going to be there for you – and why would you trust him, if he isn’t there for you know either”

    1. 47.1

      Thank you. Amen!

    2. 47.2

      Some people are more irresponsible and seem to need more help than others.   I would say lose that irresponsible person from your life.   They can’t seem to manage without you and need you to act as a parent bailing them out financially all the time.   We are talking about adults right?

  8. 48

    @ Shalini #44

    The scenario was an attempt to play “devil’s advocate”. Just that there *could* be another plausible reason behind Bob’s Gf thinking he should help her out besides plain ole’ greed.

    If they had ever talked about a “future together” the woman may have made the mental/emotional leap that they were already partners in life. The error here might not be greed as much as communication, which has already been suggested.

    Since we will never know these people, and it is highly unlikely we will ever hear “the other side” of the story – it leaves us free to speculate wildly. Wheee.

  9. 49
    Karl R

    Honey said: (#23)
    “the BF’s an attorney, so he has written a contract for any time I’ve lent him any money, always with a proposed repayment schedule for large amounts and a clause that says that he will repay in full immediately should I demand it.”
    casualencountersblog replied (#25)
    “That’s HYSTERICAL. I’d die laughing if anyone I cared about presented me with something like that when they needed money.”

    Honey’s idea makes sense, especially since her boyfriend has been borrowing thousands of dollars from her. Even if they break up, she will be able to collect from him. Even if it’s a nasty breakup.

    Bob hasn’t specified how much help his girlfriend needs each month. It could be $100 or $1,000. But she’s in graduate school, so she’ll probably need it every month for 2-3 years. That kind of money adds up fast. And unless it’s a loan with a written contract, he’s not likely to see a dime of it if they break up.

    And if you’re keeping your significant other financially afloat, it’s easy to begin wondering whether that’s the primary reason they’re staying with you.

    Honey’s idea makes sense.

  10. 50

    @Kristyn #43

    When I hear the phrase “My man” or “My woman” I think of old westerns. Lol.

  11. 51

    This is what I would do if I were in Bob’s situation. I’d sit by myself first and decide whether I wanted to marry this woman. If the answer is no, then I would leave the relationship. If the answer is yes, then I would tell her I felt uncomfortable about giving so much money to someone who wasn’t family, and ask her if she would marry me. This is the most straightforward way of dealing with the problem. In any case, I would not give thousands of dollars (which is presumably what she wants, though Bob doesn’t say) to someone to whom I’m not related.

    1. 51.1

      Because marriage cures all money problems.   Take it from me, marriage makes it worse.   Someone who is bad with money will always be so.   They will drag you down like a sea anchor.   Plus, when you are married, they are now entitled to half of what you have.   God forbid you have kids with them, the costs only go up.

  12. 52

    I can’t imagine being on either side of this scenario. I would need to be married to someone before agreeing to help fund their education. In fact, when my ex and I were talking about getting married, I told him that I would help cover the bills if he wanted to go to grad school full time. But if we weren’t married? No way. And I would never expect to expect a guy I was dating or in a relationship with to do that for me. That’s what family is for.

    I would be sympathetic to her if this was due to some sort of emergency, but without knowing details it really just sounds like poor planning on her part.

  13. 53

    The way I see it, is that relationships are confusing enough without trying new or unconventional ways of doing things. I think that if a single woman needs money and she cannot make more or spend less, then she has to go the conventional route and borrow from the parents or from the banks.

  14. 54

    Evan is totally right — don’t ever bail someone out unless you plan on being a de facto crutch – it’s not that you mean for it to happen, it just does. No matter the reasons — we are all adults and capable of making choices and decisions — this girl could have chosen to sell her condo or whatever before going back to school since money would be tight — instead she relied on someone else. Just my two cents — and trust me, I’ve been there. It’s never good — never never never. No matter the circumstance. You can’t guess at someone’s motivations — just don’t bail them out.

  15. 55

    Having this problem come up 9mos. into the relationship can be looked upon as an opportunity: to evaluate what each of their expectations are regarding money management and partnership. They may have completely different models and “styles” when it comes to saving, spending, who should pay for what, and financial goals.

    Better to explore that while dating and see if they are compatible in that area, than to just assume they will be after deciding to live together.

    1. 55.1

      I have a problem with the 9 months.   Is that really long enough to develop a completely trusting relatiOnship?   Seems to me that they are in the beginning of a relationship, unless they have been friends for several years before becoming an intimate couple.   She would have more to prove to me before I lay out the cash.   There are several levels of the relationship that must develop and that can’t be done n 9 months. So I can see his apprehension.

  16. 56

    If Bob has to write to EMK about this….Bob’s girlfriend, must have large breasts, and/or, she is good in bed. Bob, if I left her, I would have withdrawal symptoms also.

  17. 57

    Dear Guys and Gals,

    Thanks for your responses. In answers to some of your comments:

    1) She’d like us to get married. I got burned in a divorce several years ago and am not currently in the marrying mood. I am interested in a LTR, though.

    2) She budgeted for her 18 months of schooling and her living expenses, and all was going well until her car died. Without a car, she lost almost 3 weeks of work. Since she had no savings, the lost paychecks and the need for money to buy a car was more than she could handle.

    3) I suggested that she abandon her house or get a roommate, but she refused. She hated to lose what little equity she had in her house, hated the thought of having to move with her 3 kids, and was uncomfortable with a stranger living in her house with her kids (and the family barely has enough room as it is).

    4) At the time she asked for this money, we’d not slept together for almost 2 months. She’s a religious woman, and she began to feel guilty about having sex outside of marriage.

    5) I sent the question to Evan about 6 weeks ago. Since that time (and obviously before I could read his and your answers) I loaned her $1500 to get caught up on her mortgage and other bills. I will be giving her no more money, and she knows it.

    Thank you all.


  18. 58
    Curly Girl

    Hunter: Your idea occurred to me, too. Back when I was asking the question about where the sense of entitlement came from, that his $$ was hers, only 9 months in, and his talking about enjoying the relationship but not expressing any deep feeling for her. Somehow she has the idea that he’s going to give her the money. Why would he be buying into that for even the time it takes to write his question?

    And why would she be thinking she can get away with it? Because she can. (To borrow EMK’s phrase from another context.)

  19. 59

    Married women struggle with guilt issues also.

    For some women, an LTR, is, three months long.

  20. 60

    @Bob #57- thanks for writing in with more details!

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