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.

Join our conversation (204 Comments).
Click Here To Leave Your Comment Below.


  1. 1

    I had a very different take on this situation than Evan did. I didn’t get that she’s trying to exploit him, but that she genuinely views them as partners and likely sees the relationship as more serious/permanent than he does.

    That doesn’t make it right; I think it’s a piss poor idea for an adult woman to be financially dependant on anyone, married or not. Hopefully she’s getting the type of degree that will provide a positive ROI in terms of real dollars and she won’t find herself in this situation again. But it does mean that her crime is being naive and a bit misguided as opposed to being an exploitative gold digger.

    What made me read the letter in a more sympathetic way was her ‘i’d do anything for you and we’re in this together’ reasoning versus ‘you’re a man and it’s your job to take care of me’. Had she said the latter I’d see a problem, but that didn’t seem to be her attitude here.

    1. 1.1

      Easy to say what you “would” do when you got your hand out.   You “would do” anything and it means  nothing.   This woman is exploiting.   She put herself in an untenable situation and then dumps it on her boyfriend who could afford it because he has a job.   This situation has a really bad ring to it, rally bad!

    2. 1.2
      S M

      If she is truly in this relationship, she should not break the relation beacuse of this issue. Otherwise she is just not really worth it

    3. 1.3

      Independent working woman will never ask for money. She is doing so thus once her boyfriend stops giving cash , I am sure she will dump him blaming that he cannot provide for her. Suppose this girl marries this boyfriend and the boyfriend for some reason stops earning. Then you can very well assume she will leave him because she is under impression her boyfriend is to spend for her and not the other way round.

    4. 1.4

      To me, saying ‘I’d do anything for you’ when asking for money is emotional blackmail. It’s unfair. She sounds entitled. She has choices, she can sell her house/apartment or get in a roommate. If he wasn’t around, what would her choices be? It sounds like she may have put herself in that situation (going back to school) thinking of her boyfriend as her back-up plan. That’s wrong, unless HE made the suggestion in the first instance and told her ‘I know this is really important to you so go for it and I’ll support you’.

      I hate it when people pressurise others to help them out financially.

      1. 1.4.1

        Emotional financial blackmail is very unfair

    5. 1.5

      Yes when I met my ex he had no cent, only thing in his fridge was a bottle of water and I had enough so I gave him. A friend also dated a guy w no money but she had it and didnt give him. I didnt get that. Then why date him? If you want your money for yourself or a rich spouse date someone else.

  2. 2
    Karl R

    Bob said: (original post)
    “She says that since she would do anything for me if I had problems,”

    Maybe she would. Maybe she wouldn’t.

    Relationships are a two way street. As much as we talk about “unconditional love” in relationships, there’s a lot of quid pro quo in the early stages. (Familial relationships, like parent-child, are an exception.)

    How does someone become my confidant? They confide in me, and they don’t betray my confidences. I don’t start out by discussing my biggest secrets. I start with smaller stuff and see what happens.

    I’ve loaned friends $1,000 or more, but it wasn’t the first loan. I loaned them a small amount, and they repaid me. I loaned them a larger amount, and they repaid me. Eventually they had built up the trust where I felt confident that they would repay larger amounts. And some of them loaned me money too.

    It doesn’t sound like Bob’s girlfriend has taken the necessary steps to prove that she would “do anything” for him.

  3. 3
    Curly Girl

    Hear, hear! Dump her!

  4. 4

    My reactions to this:

    1) Is there ANY reason this woman can’t get student loans like EVERYONE ELSE who goes back to school and finance her life that way? If she hasn’t taken them out, it’s not too late to start – you can file your FAFSA late and/or ask for a budget reevaluation that will increase the amount of her aid. If things continue to go well with these two, then perhaps they will get married and he will feel differently about paying her loans off than he did about paying for her lifestyle upfront (or maybe she will make enough money after the additional schooling to pay them off herself).

    2) If everything else in the relationship is good and this is only making him uncomfortable because they aren’t engaged/living together, then perhaps she should sell her house (or he should sell his) and they should move in together. FWIW, this is one of the reasons I will NEVER buy a house. You can always downgrade easily if your life situation changes and you are renting. The same is not true, as we have seen over and over in this economy, if you “own” (I put own in quotation marks since if you don’t have your house completely paid off you are really still renting from the REAL owner, which is the bank, only you get all the liability – in what universe is that a deal?).

    3) Observation from my life – this isn’t really a gender issue or an income issue. It seems to me to be a money-management issue, which is totally separate. I have lent the BF thousands of dollars on numerous occasions, including a) when I was still in grad school making $14K per year and he had graduated and was making $90K, and b) now that I’ve graduated as well but am making less than half of what he does (he has about $7K on one of my credit cards because my interest rates are so much better than his).

    He is very responsible with money *now* – has paid off about $15K in credit cards and not made a single charge to the plastic since he started working, but he is digging himself out of a VERY deep hole that was accomplished either before he met me or when we had been dating less than a year and I didn’t really have a say (or even know anything, since I didn’t feel it was appropriate to ask yet) about his finances. If I wasn’t confident that he’d learned the error of his ways then I wouldn’t be dating him or lending him money. As it is, I am confident in our future.

    However (again FWIW) there is no way in HELL I would have loaned him money when we’d been dating less than a year. At that time, I would have run as fast as my little legs could go. But that’s hardly blanket advice for anyone’s situation – this one may be different. Only Bob can say.

    Honey´s last blog post…Crummy Weekend

  5. 5

    Wow, I’m really looking forward to reading other people’s comments as I have not thought about this issue whatsoever. I’ve never been in this situation.

    Evan has a great point. If the situation was inverted into a guy not thinking his finances through before making a big commitment, then asked his girlfriend to supplement his income and pay for his short sightedness there would be a chorus of “throw the bum out” from men as well as women.

    It isn’t that neat and clean.

    Contemporary American culture is fairly heterogeneous in what it expects from adult females. Even limiting things to just my own social circles, I know happily coupled couples who take care of their expenses like single people would on one extreme and on the other extreme I have a friend whose husband pays all of the bills despite them not having children.

    Whether a given woman is irresponsible, has unreasonable expectations for the men in her life or not comes down to the particular people you talk to.

    I women friends in their mid thirties who take thousands of dollars from their parents and who have not taken a dime from anyone since their teen years. All them consider themselves to be responsible adults.

    I think it was shrewd of Evan to suggest drawing the line at wives, live in partners or women with that potential.

    A relationship with a GF of nine months could end tomorrow. In that situation getting stuck with 1-2 loans of a few hundred dollars is one thing but getting stuck with much more would be another thing altogether.

    I guess it is time for contemporary American men to begin evaluating women by how women handle their finances and their financial expectations of men. Do you want an old school woman, a woman who views her finances the way you would for yourself or the hybrid who take care of yourself but who would view you as an acceptable backup?

  6. 6

    Jennifer Jun 18th 2009 at 05:56 am 1
    I had a very different take on this situation than Evan did. I didn’t get that she’s trying to exploit him,

    Why do you have the impression that Evan though the GF was trying to exploit him?

    What made me read the letter in a more sympathetic way was her i’d do anything for you and we’re in this together reasoning versus you’re a man and it’s your job to take care of me. Had she said the latter I’d see a problem

    Interesting. I thought I read exactly that with this line from Bob’s letter:

    since she says she really can’t stand the thought of her man not helping her out if he can afford to do so.

  7. 7

    I think Karl in post #2 bring up a good point.

    Bob’s GF is expecting something that happens in relationships that are established past a certain point. It doesn’t seem clear to Bob if they have passed that point yet. Evan tried to define that point as wife/live-in level relationship.

  8. 8

    @Steve #4 I think your quote below is right on:

    I guess it is time for contemporary American men to begin evaluating women by how women handle their finances and their financial expectations of men. Do you want an old school woman, a woman who views her finances the way you would for yourself or the hybrid who take care of yourself but who would view you as an acceptable backup?

    People need to talk about their expectations, and the state of their relationship, so no one is confused.

  9. 9

    An interesting way to look at this is to imagine they are in the future telling someone else about the breakup

    “My girlfriend and I broke up. She ran into financial trouble from a poor decision she made. I loaned/gave her several thousand dollars. It became clear she would need a lot more. I didn’t want to go there”.

    I broke up with my boyfriend. I made some bad decisions and ran into financial trouble. He gave/loaned me several thousand dollars. I needed a lot more. He didn’t feel comfortable giving more money. It made me upset, so I ended the relationship

    Which sounds worse to people?

    1. 9.1

      She wouldn’t tell the truth. If she would break up over that she would make up something like he cheated or abused her so the next guy would try to one up him and give her the money.

  10. 10

    Hmmm, well it would seem her field isn’t mathmatics or accounting if she couldn’t figure out she wouldn’t be able to pay her basic household expenses with a parttime job.

    Sounds like she sees them as partners. Bob doesn’t. I think it’s pretty presumtuous of someone to expect someone else to “help them out” when they aren’t living together or engaged, but who really knows what these people’s relationship is really like? Obviously they are not on the same page and this appears like it will be one of those “piss or get off the pot” turning points in the relationship.

    Bob it you really “don’t like the idea of giving anyone money”, you are better off avoiding partnerships and sticking to “just dating”. Also, for God’s sake man, DON’T Have Kids!

    1. 10.1

      Ok so, first of all I wouldn’t ever listen to someone that can’t spell “if” correctly and I’m not going to say Selena’s name but oops. Try proof reading, they taught it in grade school. Best advice here is to start relationships with your own kind. This means middle class people Marry or start relationships with middle class people or rich people marry rich. Whatever happened to dating people that have some of the same things in common which includes finances located at the top of the list.

  11. 11

    @ Steve, I think her version would be more like:

    I broke up with my boyfriend. I was going back to school so I could get a better paying job, but it made things financially difficult in the short term. He loaned me a little bit of money, but wasn’t comfortable giving me what I actually needed to get by. I thought, if he’s like this now, how will he be if we stay together? So I ended the relationship.

    Honey´s last blog post…Being Tall vs. Great Game? Take the Game.

  12. 12

    The biggest problem is that you’re dating her and not married to her. I’m not into being a sugar daddy to someone I’m dating. If you’re married, you are spoiling her or just taking care of her.

    He needs to get used to being a sugar daddy or break up. The only 2 choices I see.

    Eathan´s last blog post…I’m Not Dating Any Longer

    1. 12.1

      I am in the same situation, although in my case, I work and am saving money to pay for my education. However, my ex girl and I were really close, and I’ve been there for here each time, bailing her out financially. I listen to her each time she has a problem. recently, my girlfriend started taking loans and asking me to help her repay. My ex is in really deep financial problems, which I wudn’t mind helping. However, I feel that both of them are entitled to me helping them out because I am supposed to be the man. I have thought through and thanks to the advice I read here, I am ending both relationships for good.

      1. 12.1.1
        Giffy McDrawing

        women will burn through your money and then ask. “Why should I stay with a poor man?”

        1. Tommy

          So well put. This is so true.

      2. 12.1.2

        i have and fixing to be departed from a similar situation with a younger woman who will be homeless if i stop helping her unless shes really an undercover cop. And at this point im not sure which is more real. Since she hangs out with women and men police frequently. And im not sure what level. But on my end i had falken in love with her and though we never have had src in the two years ive known her she always broke. Ive helped her ALOT. My reasoning was if i had mot been helped ALOT at a phase in my life i would be homeless too. Were breaking up because she borrowed my phone last week cause hers was broke she said. I found out yesterday she had another that wasnt broke she borrowed. When she went missing for about 24 hours i thought hey i can track my phone. And i did, and found my phone and her car at a house in town that was or is owned by a police officer. Whether thats who owns it mow or not i do mot know but from a property search it fits. I told her i tracked and shes mad as hell. Is planning on meeting me today to return it but doesnt want to bring it to my house i guess cause i live far out om not sure. A cop lives close by. So id say to anyone amd have heard it before to follow your heart. I used to be a police officer in my younger days for a brief period might be why i am suspicious at times. I got burned badly on a divorce also. Even with all thats happened id still help her though she wants me out of her life , she says. I may be a fool. When you feel like your in love and have been ostracized by society and a woman shows you affection nobody else will give you, being played or used can happen easily with your eyes wide open and enjoy it.

  13. 14

    What is unclear is if they are living together or not, also, “we have enjoyed each other immensely” can mean different things. If he is “enjoying” having a girlfriend who although may not technically live with him, but is over all the time and acting like a live-in girlfriend/wife, then it does not surprise me that she expects him to act like a live/in boyfriend/husband. Nine months of continuous exclusive dating may lead her to feel that way, or he led her to feel that way. I’m sure she told him of her plans. No one gets into school overnight, there is an application process, she has a mortgage-not rent, a mortgage, so I’m not buying that this is a surprise. There was NO discussion about her working part-time? Nice of him to help her out, but some of this he should have been talking about with her. She’s not totally irresponsible if she owns a house. I appears that she feels the relationship is on one level and he wants it to be a bit less of a committment. Would not classify her as a golddigger or him a sugar Daddy, but if he doesn’t like it, then he should leave. Oh and these will not be loans, he might as well write them off as gifts. I would imagine her take is, my man takes care of me when I need help.

  14. 15

    She is OUT OF LINE ! And Bob is being used. I, as a woman, would (and have) bent over backward never to ask for a loan from any man. If you are married is one thing but not even engaged would do. If you want him to be your future husband, do you want to look financially irresponsible to him? I don’t think so! And good point made above, that you could break up at any time and you’d never see that money again, or you could get her thru school and then she could dump you!

    1. 15.1
      Just No

      Also it is a good sign of how this relationship will be long term, she sounds like a taker to me I have a pal who married one of these and now pays for EVERYTHING and does not realize that is not alright. The relationship only “got better” after he decided to “give everything to be with her, do whatever she wants to make her happy” and he is so obviously being used by her like all her (evil ex’s) probably were, oh and it has only been better for the past two months after almost two years of roller coaster crap and way over 20 breakup makeups including four right before the wedding. Poor man is giving up all his dreams for her, all his savings, his home, his friends, everything, and oh yeah she is over 38 and acts like a pre teen. And years before they were even official he paid for her lifestyle and her grown child’s, because he “loved” her.

      Bob is being used like my pal is, and no amount of “love” will change that, I would get out and find a normal woman pronto; I made it through college by cutting back and learning to live frugally it isn’t that hard to do and if all else fails you can get loans.

      She could also be like my little brother too, going to “college” for a few semesters (his is military paid) then flunking out or forgetting to register in time and spending the money elsewhere. Then when his sibling is graduating he tries to “register” again but misses the deadline then claims that it is because X,Y and Z reason.
      Rinse and repeat for three semesters, and she could do that you know.

      Bob I would get out, you do not want to be in a pay to play relationship they never end well and you will lose far too much in the long term.

      1. 15.1.1

        You make a good point i wished i had read before making a previous comment.

    2. 15.2

      I agree !!!

      well said

  15. 16

    I don’t think Bob asked this explicitly, but I think he wants to know if there is a way he can stop lending/giving money to his girlfriend and not have it impact the relationship.

  16. 17

    What a conundrum! I completely agree with Donna’s post and sentiments. Boy, Suze Orman would have a field day with this woman. In this economy, we are all forced to cut back and tighten the purse strings a bit. If you can’t afford to get an advanced degree (in addition to paying your bills) then maybe now is not the time to go back to school! Bob sounds like a generous soul, but this scenario is a recipe for disaster. Sounds like his GF is manipulating him and he is falling for it hook, line and sinker. I guess love really is blind.

  17. 18

    If you watch those court TV shows, like Judge Judy for example, their court rooms are filled with people who loaned money to others – usually girlfriends to boyfriends – and then they say it was a “gift” when they break up. Always in an uncommitted relationship. that what is the beauty of a marriage…what’s yours is mine and what’s mine is yours, and we make decisions and sacrifices together for the common good. I personally agree wholeheartedly with Evan and a little more strictly in fact in that I don’t think, in any circumstances, should there be co-mingling of monies unless the two are married. Not in a “comited” relationship, or “living together” because what is that really? It’s not a marriage and frankly demeans marriage. It always seems to end in trouble when one loans money to another out of wedlock. This girl is trying to hold him hostage by saying essentially “I’d do the same for you” and “I can’t even think of having a relationship with someone who won’t help me”. My advice for him is to gently move on, or be prepared to state your case and stand up to her like a man, regardless of how she reacts.

  18. 19

    Whatever happened to student loans? Oh yeah, right, she’d actually have to pay back a student loan. Even if she isn’t “using” Bob, it doesn’t sound like she is financially savvy or independent. She is not “entitled” to a loan from the Bank of Bob just because he makes a good income. Plus, he already HAS helped her out financially, so I don’t think he’s stingy.

    I’m sorry, but she should have had a plan for paying her own way without relying on her boyfriend at this point. I could see it if she involuntarily lost her job and was perhaps caught off-guard. But she made a decision to return to school and she should have worked out a way to do that AND pay her bills, including an expensive mortgage. They don’t live together, so it’s not his mortgage to share.

    I think Bob is having second thoughts about being involved with a woman who is isn’t financially responsible, and who doesn’t seem to see anything wrong with that.

  19. 20

    I agree with the general consensus that she is out of line asking him to borrow money at this stage of the relationship. If he saw her plight and offered, it would be a different story, as it would if they were engaged or living together.

    I think whenever you loan someone money informally, you have to be prepared to never see it again. If you think of it as a gift, or that it will come back to you in another way (a raise, a bonus, etc.), it makes it a lot easier. If people thought, “What if I never get repaid?” they might make a different choice about extending a loan.

    I’m from a big family, and we’ve all loaned each other money at one time or another. I don’t know how desperate I’d have to be to borrow from a boyfriend of nine months, especially if I owned a home. I don’t share my personal finances in any great detail with someone I’m dating–I don’t think it’s any of his business until we’re talking seriously about cohabitating. That’s one of the perks of being single after having been married to a man who was controlling and obsessed about money–how I choose to spend it is my choice.

    I heard the women on “The View” talking this spring about how singles are asking each other their credit scores instead of their astrological signs. Good lord, have we come to that? I’m sure there are a lot of people who will only date someone who is financially responsible, although that in itself encompasses a pretty wide range of behaviors (no debt? having manageable debt? having lots of debt but paying it down?).

    I myself prefer to date someone who is at roughly the same station in life as me–it makes choosing a restaurant, planning a vacation, understanding budgeting for college tuition, etc., easier. But I’m comfortable gleaning that information during the first few weeks of dating, rather than demanding it before the first date even takes place. And there’s no guarantee that asking gets you an accurate or permanent answer. Especially in this economy, people’s credit scores and monetary assets can change daily. Payoff your mortgage and decide to rent? Your FICO score actually goes down. Open a new credit card with a high limit ? Your score goes up. A millionaire can have a reversal of fortune in the stock market and become penniless in no time. Businesses fail. Property values decline. My goal is to simply try to start off on the same footing and with similar (or at least compatible) values about money. After that, if you are really with someone for the long haul, married or no, there is an element of “for richer or for poorer” that comes into play…

Leave a Reply

Your email address will not be published. Required fields are marked *