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

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. 61

    ***Applause**** for Evan’s response. I like money as much as the next girl, probably more so. haha. Sorry, part of my academic background is in finance, so I live and breath investment bankers. Well, that aside… IF Bob had wanted a sugar daddy relationship, he could have gotten one at the start. And if the woman is seeking to turn it into one, she can state her demands, and Bob counter with his own requirements. I can totally roll with that because I can be as superficial as hell. What’s NOT appropriate in my opinion is for a woman to be sooooo misguided, deluded, and assine, as to turn a relationship which she maintains is based on trust and love, and then guilt trip the guy into giving her money.

    She says she would do anything for you if you were in trouble. By anything, she obviously didn’t mean making enough sacrifices to make sure her own sh*t was together enough in the first place. No one is entitled to an advanced degree, and I bet she isn’t going for her MBA or law degree, but rather some self-indulgent crap. Bob you make 100k’s, I bet you had to slave for years, if not a decade, to gear up you own earning potential. That if anything, should be saved up for your own future, and your own future family, not some over-entitled, out-of-touch, guilt-inducing shrew.

  2. 62

    @girl-with-glasses, post #61.

    Please don’t hold back, let us know how you really feel :-).

  3. 63

    I have to write that I have been finding most (not all) of the responses from the women in this thread to be refreshing.

  4. 64

    My answer to Bob’s question is a very simple one and it doesn’t involve speculating about the character, intention or financial responsibility (or lack thereof, according to most people on this blog) of a woman and a situation about which we know very little. Give money — don’t lend it — give money to people you really and truly want to help. Only give as much and as frequently as feels right to you. If for whatever reason, you don’t want to give them money, don’t. It’s that simple.

  5. 65

    Since this woman wants to get married and Bob doesn’t…I wonder how they will work that out?

  6. 66

    That begs the question(s): did she want to get married before the financial crisis that precipitated Bob’s letter? That is, does she want to marry Bob, or the Bank of Bob?

  7. 67

    “..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.”


    It’s one thing if a guy treats on the first date becasue he likes the girl and WANTS to pay. It’s another if he’s paying her tuition at her request. And they’ve only been dating for 9 MONTHS!!

    I would never dream of asking a guy to subsidize my motgage. Ok, maybe after we’re living together/married, but c’mon.

    Being asked for money early on in a relationship like this is a red flag. Men or women (yep, I’ve known women who’ve lent guys money, only to have them blow it on stupid stuff and run off).

  8. 68

    Bob, thanks for the update.

    As with anyone who writes a letter to a blog, the ‘main theme’ overtakes the real issue. In other words, this isn’t about the real “Bob”.

    It sounds like you’re handling the situation, but the money thing raises a good point about relationships and trust.

  9. 69


    Can’t help but wonder if this changed after she got the money…

  10. 70

    I see the words “borrow” and “lend” (or “loan”) a lot in this thread, only she is not borrowing the money, nor is she asking him to lend her some.

    If a man is in love with me, and he is very comfortable while I am struggling, I’d expect him to foot the bill for certain things, too (like, vacations).

    And, quite frankly, the better off he is financially, the more I’d expect (again, IF I myself am struggling).

    Because he doesn’t have to be with me specifically, but chooses to, and because that’s my general idea of generosity and magnanimity (not to mention, love).

    Only nowhere does Bob say that he loves her.

    Well, there you go, that is your answer.

    Also, the fact that Evan’s response is equivocal, doesn’t exactly give it power. If she is the one, then all bets are off, and if not, then there are all these rules to follow. Granted, I cannot believe someone would count on their SO like this only 9 months into a relationship, but I feel that one can’t use expressions like “gold digger” or “sugar daddy” if apparently the standard is not the same for every situation.

  11. 71

    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.

    Can’t help but wonder if this changed after she got the money…

  12. 72

    All that drama was for measly 1500 dollars?

    Like I said, I have loaned people money – in a situation where I was giving my last savings – if they have been important enough for me. If money is more important, then I just don’t.

    I think that I am worth more than money, and I sure as hell wouldn’t have ANY sex with a person to whom I couldn’t loan a a few hundreds to a couple of thousands of my savings. I put my mouth where my money is.

    I have to say, I wouldn’t date Bob – why would I give a piece of myself to someone to whom money that he has no shortage of are more important than helping someone who he says he cares – and someone who is working for their common future.

    No wonder I am single, and I like to remain that way. If I can’t trust a man as a person, I don’t want to be intimate with him either.

    (And no, I haven’t loaned money from men, but I have loaned money TO men, and I got it back too. I credit it to fact that I do know how to judge people and I am seldom disappointed. Only when I haven’t listened my own judgement and listened what “others” think – then it has been the time, when I have got negative results.)

  13. 73

    “Madam, we have already established what you are; now we are simply negotiating the price.”

    –Winston Churchill

  14. 74


    Sounds like the relationship was winding down anyway.
    She no longer wants to have sex outside of marriage and you aren’t interested in marriage, right now, or with her or whatever…..

    I think giving her the $1500 was a kind and generous thing to do for someone you obviously care for and have been with for many months, but to continue to ‘help’ her out financially when the two of you don’t seem to be headed for marriage seems pointless and a bad idea. You’d resent it, she’d continue to expect it or view it as the two of you are more committed than you are.

    Maybe her cutting off sex and asking you to help her were little tests to see how much you truly care about this relationship?

    Friends, family, lovers help each other out with money all the time and that is fine, but when it becomes expected (which she seemed to feel) it’s rude.

  15. 75

    Response to Joe #73:

    Really? Sounds to me like somebody wasn’t getting the proverbial milk “for free” as they had hoped.

  16. 76

    While we focus a lot on sex and money on this blog perhaps there were other things that were happening in the relationship that made Bob’s lady feel the relationship was more committed. For example, was she cooking for him on a regular basis? Was she doing his laundry, running errands for him, taking care of him when he was sick, helping him host gatherings for business associates, friends, and family? There are a number of things that she could have been doing for him — not just sex — that suggested to her they were quite serious. Why must we always assume that everybody is out to get something for nothing.

  17. 77

    Another thought I had: a single mother of three would never make such a drastic decision if she didn’t think she had a shoulder to lean on.

    I really feel for her, actually. She is now in this awful unsustainable situation because of poorly communicated expectations of the extent of this relationship.

    Btw, speaking of expectations: a lot of people on this board mentioned discussing financial expectations upfront, but really, is that something anyone discusses before marriage or at least cohabitation? I personally would think it premature.

    1. 77.1

      I agree. I’m a struggling single mom of 2. My ex husband isn’t financially supportive nor is he physically around to help. I don’t have any family to help either. I think the gentleman who posed the initial question came off callous and insensitive as a human. 

  18. 78

    LOL, how the heck would she have time to do any of those things for him when they, a) weren’t living together, b) she was going to school full-time, and c) she had three kids she was already taking care of?

  19. 79

    I had a similar situation with an ex-girlfriend, but to a much smaller scale.

    We were both young, and she found out that her roommate was ripping her off for $50 per month by lying about the rent. She felt betrayed and angry, and wanted to move into her own apartment immediately. She had not planned on moving, and as such, had not saved any money for a move. So, asked me to lend her $2800 to help fund the move. I probably could’ve afforded this amount without repayment, but the whole idea made me very uncomfortable. I understood that she felt hurt and betrayed by her roommate, but I didn’t believe the $50 per month (which was rectified through a conversation with the roommate) was worth her proposed radical change in living arrangements. Her new apartment, even after the initial $2800, would’ve have put us both (if we continued working as a financial team ) in a situation that could’ve dragged us under financially. My position was that it was more responsible to stay in the apartment with the roommate until we could save enough money for her to move (I calculated 3 4 moths would’ve been enough time). She disagreed and we separated over this issue because she claimed I was not willing to support her decisions.

    My point is that this type of situation is not really a financial issue at all. It’s really an issue about the stability, responsibility, and maturity of any person in their life planning (financial and otherwise). In Bob’s case, a stable and responsible (financially and otherwise) person would have lined up all their financial ducks prior to going back to school. He/she would have made a prediction of finances and dawn up some contingency plans in case things didn’t go according to plan. If that person thought that they might need to borrow money from their partner, he/she should’ve consulted that person prior to beginning the endeavor. That way the the expectations would’ve been defined and agreed to.

    In my opinion, the real problem with bob’s girlfriend (no matter what their level of involvement) is that she is not a very “together” person who is responsible in her life planning. In my experience, this type of person will continue to have problems related to poor life planning and personal responsibility for years to come. Bob, I think it’s time to cut the cord. Her poor life planning might sink you both financially in the future. I cut the cord on my ex and I’ve heard that my ex-girlfriend is back at home in New York living with her parents. I might ve been there too if I didn’t realize the dangers.

  20. 80

    @Shawn #79

    I don’t think it is fair to categorize such women as “immature”. Women are often raised, still, with different expectations. Men are still expected to take care of themselves and often take care of others. Many women, while functioning as liberated independent adults still have the expectation of a financial fallback card from their SOs.
    Thankfully, there are many women who have moved passed this and like you I would not want to date the other type.

  21. 81

    When she asks for $1.29 so that she can get a $20 dollar note instead of a handful of change at the supermarket , it’s cool.
    When she asks you to pay HER bills : not ok . Ever.
    They are not your joint assests and it is not your responsibility unless it’s a situation where she’s really broke and studying and you work all the time late and live over an hour away and she always comes to meet you so you aren’t inconvenienced . Then she may be almost entitled to ask for a bit of fuel money to get her through the week as she’s been putting in a lot of effort .
    If not , ditch her fast. I’m a 19 year old young woman and even at my age I know it is wrong and I would never feel entitled to any damn thing that isn’t mine.
    She’s a LEECH ! If you let women like that in they will suck you dry.

  22. 82

    That is exactly right Donna.
    I too aspire to be completely financially independent . Not a parasite on the backs of others. It is not ok .
    If you can’t afford something , then you shouldn’t have taken the damn thing in the first place . That is absolutely ridiculous for any intelligent person to do . If she doesn’t have two children who need to be provided with some living quarters of their own than why on earth is she trying to hold onto a property she can’t afford ?
    It may sound extreme , but I would rather end my life then be a drain on people who care and the community .
    But that is my personal take on things.

  23. 83

    This is an interesting thread. I found my way here because I’ve been trying to work my way through a not-so-different conundrum.

    Last fall I had been dating a man I adored for several months, but the relationship was in trouble because he was going through some major financial troubles. He had invested heavily in his business right before the economy tanked, and now his world was crumbling — no income, big mortgage, kids and ex-wife to support, etc.

    He came to me as a last resort and borrowed a sizable chunk of $$$ — about what I earn in 7 weeks, after taxes. (I am very responsible with money and earn a good living.)
    The similarity I see in this situation is the obligation  we feel (whether or not we act on it) to help someone we care about, especially when it would be otherwise devastating for them without their help.

    Of course, in my case, we are now broken up. He has filed for bankruptcy and says he intends to pay me back, but I don’t see him acting on it. He has no legal obligation, only a moral one.
    Bottom line, when someone you are not committed to in some way asks to borrow money, it’s just a no-win situation. In hindsight, I never would make that decision again, certainly without some sort of commitment from him. (But would  marriage with this man have been a good idea?) I did, however, enable him to rebuild his career and keep a roof over his children’s heads, so I guess I earned a few kharma points.

  24. 84

    This is a really great topic and makes me think of a situation I was in with my boyfriend recently. We’ve been dating for 3 years now and the situation is reversed. I work full time, earn a good income, and he’s in university working just part time.
    Earlier in the year we had planned to go on a vacation to Mexico right after Christmas and both said we’d save for it starting before summer.
    November came and he didn’t have the money. In addition to this, he decided to quit his summer job 3 weeks early because he didn’t like it earlier on the year.
    He outright told me that I would have to pay for half his trip to go. He had mentioned earlier I may have to *help* him out, but failed to mention it would be half…I had figured a couple hundred bucks, not that I’d be in for a $3000 trip for the both of us.
    I was uncertain and he then told me that I needed to decide or he was going to cancel me out of his holiday plans and do something cheaper with his buddies instead.
    ….I was pretty taken aback by that.
    To me this is a huge red flag in our relationship and the way he handles money along with his expectations and it’s been troubling me since then. He refuses to talk about money however as to him, it’s not something that needs to be discussed in a relationship.
    I disagree.
    So now my question is whether or not this should be a complete deal breaker for me and I should end over something like this?

  25. 85

    Shannon, #84

    I’d end it with the moocher. Not because he makes less money, but because he clearly won’t do the very least to work towards a shared goal (that you both agreed upon) and actually gave you that ultimatum – that unless you’d fund the whole trip, he’d spend the holiday with his buddies!

    A guy worth keeping would have kept his summer job and/or suggested a less expensive vacation for the two of you, one where he could contribute something. It sounds like he sees you as a meal ticket. His refusal to discuss finances should be a huge red flag!

    He sounds very immature but YOU are the one putting up with it! How did you think he would contribute towards the trip when he quit his job three weeks early? Are you planning to pay off his school loans too? Why have you stayed with this guy for three years? Does he contribute in other ways? Do kind things? Take care of you when you’re sick? Cook dinner? Run you a bath after a hard day at work? Make you laugh? Great sex, at least?

    Sometimes women (or men) stay with a partner because they’ve put in that investment of time and energy (and money) while the other person is struggling with school or depression or other issues. And they think that surely that big change is right around the corner, that this person will become what they want. So they wait, and wait. And then another three years pass. And suddenly they’ve been with someone for 15 years and nothing has changed and they’re very unhappy.

    People can change, but only when they want to. Doesn’t sound like your BF wants to.


  26. 86

    #84 & 85

    Ditto on Cat’s reponse, excellent questions to ask.  Then come up with HONEST answers and listen to your intuition and act accordingly–even if it ends up be difficult action.

  27. 87

    Thanks for both of your replies.  For the last year I’ve been really questioning things and what you mentioned in the second paragraph – staying for the time investment/comfort level is really where I think I’m at.
    Earlier things didn’t bother me as much as we generally had fun and I was concentrating on my career so my real focus was elsewhere. But now I’m 27 (he’s 23) and am just seeing large red flags pop up and differences between us that I don’t think are going to make it work.
    As for the questions, sadly, it’s no to many.  Sex is a huge issue with us (I’ve never been satisfied – earlier on satisfying us was enough). I do have a lot of fun with him when things are good, but it’s been a VERY rocky relationship to say the least and despite my mind knowing that I should have ended it a long time ago I haven’t been able to do it.  I think this whole financial thing though is what’s really opening my eyes and getting me seeing all the other issues more clearly.

  28. 88

    #87 Shannon

    Sounds you came here Shannon to get an outsider’s opinion on what you already know in your heart and gut.  🙁  Not every relationship we have is meant to be ‘it’, as a matter of fact, I believe it’s difficult, but NOT impossible, to find that person who makes us feel ‘all that’–so we have to go through experiences to put us in the position for Mr. Right to be in our lives.  🙂

    If I were in your shoes, this is what I would be thinking:

    1.  I just spent three years with this man.  I would know by now if he’s ‘the one’.  What does my intuition say?

    2.  What have I learned from this relationship?  What can I take away from it that will benefit me in the future?

    3.  If I muster the courage and do the right thing now (even though it may be uncomfortable), it’s that much sooner that I can work on getting over this relationship, while working on myself, so I can be ready for the next man that I get involved with.  The longer I wait, the longer it is to start the healing process.

    Good luck Shannon!  You sound like a contemplative, aware young woman, that will serve you well.

  29. 89

    Thanks for the response back. You definitely raise some good points and it is where I’m at right now.  I’m so bad with break-ups; in the past I’ve run from relationships for fear of it getting so serious and  having to face a break-up, but now I’m not sure I have a choice.
    Earlier on our ‘issues’ were minor in nature and not what I’d consider to be red-flags, but lately more and more are just showing up that I can’t ignore.
    You’re right in everything you said though. Now I just need to take action…easier said then done sometimes. Thanks for the good luck!

  30. 90


    Shannon, NO ONE is good with breakups!  🙂  It SUCKS!  Just saying to someone have a few dates that you’re not feeling it, SUCKS!

    Breaking up is ABSOLUTELY easier to say than to do. 

    That’s what having courage is all about though, doing the right thing even though we know it’s difficult/painful.  Only by doing courage do we grow.  Once you have some distance, you can really focus on the relationship and what you learned from it, make it as positive as possible.  This is just a step in your life. 

    You’re setting yourself, AND HIM, free to find others who are much better matches for each of you.

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