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. 21

    @Steve # 5

    Hey Steve, I got the exploitation theory from this line of Evan’s response:
    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.

    Earlier he also mentioned that Bob was being used a sugar daddy.

    Regarding the line in the letter that you pointed out, i didn’t read ‘man’ as in ‘it’s a mans job’ but more like ‘my man/partner/significant other should help me out’, with the assumption that that would go both ways.

    Like Selena and Karl said earlier, i think they just aren’t on the same page regarding the ‘seriousness’ of their relationship, not that she’s being exploitative.

  2. 22

    On a side note, 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.

    So perhaps that’s a possibility…and if she’s hostile to the idea, then we know where she’s REALLY coming from.

    Honey´s last blog post…Crummy Weekend

    1. 22.1
      we say

      I always wonder about these relationships that have prenups and contracts. As it is, I find it sometimes hard to have my d#ck stand up with a woman who love me.

      so how the hell would I manage to do one with one with a loan contract in my pocket

      1. 22.1.1

        Given the legal undercurrents and prevalent Court decisions on partnership  dissolution, a prenup  SHOULD be compulsory, whether we consider marriage or cohabitation (which quickly turns into common law marriage in many States).

        Simply put: if both partners have identical financial resources AND contribute equally  to expenses and purchases, that prenup may serve little purpose.

        BUT, not all relationships are on an equal $ footing, and situations may change (job loss, incapacitation, depression, etc.), so why expose yourself to easily avoidable trouble?

        Also, the wo/man with whom you enter a relationship IS NOT the wo/man you leave (or that will leave you). Resentment, anger, revenge,   malicious vindictiveness, may come into play. Even if nobody is really at fault!

  3. 23

    @bdsista , post #12

    If you were dating a man for 9 months and he told you that he was quitting his job to go to school would the thought occur to you that you might become the goto person for large sums of money if he got into trouble?

  4. 24

    @Honey post #6

    About item #2
    What about equity? If you HAVE to sell your house for less than it is worth you still get something back, with rent, it is 100% gone. If a bank forecloses on you, don’t they at least have to give you what you paid on the principal back?

    About item #3
    Its not a gender issue, for you. It may be for others. As I wrote in comment #4 there are a number of ways for women to view their relationships with men and money in contemporary America that would still allow them to think of themselves as responsible adults. Yes, outside of old school men there are men who would have no problem taking large amounts of money from their women but that is a lot less and a lot newer than the reverse.

  5. 25


    Seriously? That’s HYSTERICAL. I’d die laughing if anyone I cared about presented me with something like that when they needed money.

    You’re hung up, America. Life’s too short.

    casualencounters.com/blog´s last blog post…XXXblackbook.com review

  6. 26

    @ Steve, #24 – no, if a bank forecloses on you then they keep EVERYTHING you’ve paid. Even if you still only owe $5. In fact, the more equity you have, the more aggressively banks will try to foreclose, because the more likely they are to make money on the deal.

    All the personal finance literature I’ve read says that you never get it back either way. Yes, if you pay it off completely you don’t have to pay rent anymore. But you still have to pay property taxes and homeowners’ insurance. OTOH, if you invest what you would have put down on a house in a diversified portfolio with an 8% yield, then the lump sum you have upon retirement is likely to be enough to pay your rent until you die, anyway – and you still have the added mobility of being able to downsize or relocate at will, PLUS no homeowners’ insurance or property tax. Home ownership’s a crock, and especially since the bust, ALL the personal finance experts I’ve seen have said that you should NEVER think of your home as an investment. It is a place to live and that’s all.

    I am hard pressed to think of any guy under 30 who wouldn’t hesitate to take a bunch of money from his GF. This is a (horrible) generalization, but this latest generation expects to be taken care of by someone for their entire lives, based only on their own supposed “awesomeness.”

    When the BF quit his job to go to law school, his GF (who made substantially more money than him even before he quit AND owned the house they lived in), quit her job, MOVED to where he was going to school, got a new job, bought a new house after they’d been there a year, AND let him pay only like $200 in rent per month.

    Boy was she pissed when he broke up with her with 1 year of law school left to go – she had to sell her house (which she’d owned less than a year) and move back to where she came from. Fortunately, her old company had realized how indispensable she was in her absence and gave her the original job back, with like a $20K raise.

    In any case, there are still plenty of “old school” guys left as you say. But it’s becoming more and more common for EVERYONE to expect to be taken care of regardless of gender. In higher education, they refer to them as the “snowflake generation” because they’re all so convinced of their utter uniqueness and invaluability. Is that last even a word?

    Honey´s last blog post…Good News Follows Good News: Or, LinkedIn Works!?

  7. 27
    Mikko Kemppe

    Interesting question with a lot of interesting comments. I agree with Evan that if Bob continues to give her from a place of feeling like he is sacrificing instead from open heart then he is bound to end up feeling resentful.

    I also agree with Jennifer and felt like Bob’s girlfriend is not necessarily asking money from a place of purposefully using him, but instead from honest expectations.

    In either way, my advice to Bob would be to have an honest open conversation with his girlfriend to either find a solution like Ava and others suggested, or then to explain her that he simply does not feel ready to commit their relationship into a level where he
    feels financially responsible for her.

  8. 28

    Hey Bob,

    I’ve been there and done that.

    She’s manipulating you and you’re allowing yourself to feel guilty and resentful about it. Emotional extortion, guilt and resentment do not a healthy relationship make.


    MARC´s last blog post…Never Judge a Book By Its Do Rag

    1. 28.1

      I agree with you Marc. He needs to get away from this woman.

  9. 29

    To Steve #24: The bank does not return your paid principle in the event of a foreclosure, or in any kind of mortgage situation. If you sell your home for less than its market value, you might still make a profit, but it depends on what your total outstanding mortgage balance is. A lot of homeowners owe more today than their home is worth, but in time, the market will stabilize and values will slowly go up at the pace they should have in the first place.

  10. 30

    @Honey #28 Thanks for the finance info. About the other stuff, I’ve seen many articles about what experts believe is an epidemic on narcissism. One more tainted legacy older generations have stuck the youth with. I’m glad I was born when I was.

  11. 31

    @Diana post # 27 Thanks for the info!

  12. 32

    I’ve lent money to good friends and have been paid back. I’ve lent money to good friends and have never been paid back. And I’ve been quite resentful when I’ve seen the (supposedly) good friends who’ve never paid me back go on to make/have/spend more money than I with no thought whatsoever to repaying me when I helped them out during a hard time. Especially when they knew I was a single mother with limited resources.

    Because the resentment would eat me up, I decided a long time ago I would only loan money to people I LOVED. Called it a loan, but IN MY MIND I would decide it was a gift. If they paid me back? Great! If they did not? Didn’t matter because I had already written it off as a gift. Thinking that way made it alot easier to decide whether to help out a friend, or decline without feeling guilty.

    I think Steve nailed this entire situation when he wrote: “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.”

    Why isn’t Bob, who states “I just don’t like the idea of giving anyone money able to communicate this to a lover of 9 months?

    Most of you seem to smell ‘Golddigger’. I don’t. I’m getting the whiff of, “I don’t quite want to be your partner, but I don’t want to lose you either”.

  13. 33
    Curly Girl

    So, I’m thinking that nobody thinks this is a good situation for the guy and that he should either say no/keep her or dump her.

    I am curious about where this sense of entitlement comes from on her part. I do know people who speak very disparagingly of “bean counting” and “score keeping” in relationships, but in my experience these are the people who are usually looking for someone else to pay and don’t like having the issue forced into the open (you know, the kind of date who will make sure he always stands behind you in line at that movies so that you get to the window first and then doesn’t pull out the wallet–then or at any other time).

    This situation here is really rather like the “who pays for the date” issue, but writ large.

    Though truth is, I’ve seen this behavior in both dates and friends. Some people are just rude.

  14. 34

    Hmmm. She says she would do “anything” for him. But that apparently means anything except being financially responsible for herself and her work/school/home/lifestyle choices. Talk is cheap.

  15. 35

    What Evan said is right. I wouldn’t burden a guy with financial issue unless he is my husband, then it’s his right to take care of me.. Nonetheless, even if you’re her husband, i think it appropriate that she discuss with you before enrolling herself in school.

  16. 36

    @ Steve, that’s part of what I was trying to say. The other is that if they break up, they will each tell the story that flatters themselves the most and fits with their own vision of themselves. Not the story that is truest objectively.

    Honey´s last blog post…Good News Follows Good News: Or, LinkedIn Works!?

  17. 37

    I would say it’s reasonable for a happy couple to loan each other money and make it a no BS deal where she intends to pay him back at some point. I’m sure the terms would be far better than a bank loan or credit card. Honey makes a good point though, get a student loan, that’s what everyone else does, and what she’ll have to do if/when they break up. I get the sense she’s pressuring him to give the money because he’s got a good salary, which is unacceptable. Dump her if she doesn’t change her tune.

  18. 38

    @Curly Girl #33
    “This situation here is really rather like the who pays for the date issue, but writ large.”

    That thought occured to me also.

    Followed by the thought – 9 months in? What else is going on here?

  19. 39

    @Honey, comment #13

    I didn’t see any difference between your hypothetical ex-GF quote and mine on an objective level. However, on a subjective this line feels emotionally manipulative ( conscious or unconscious):

    He loaned me a little bit of money, but wasn’t comfortable giving me what I actually needed to get by

    I guess you are trying to tell me that a number of women would see it as getting a reality check of the status of her relationship. He wasn’t ready to make a significant sacrifice on her behalf, so the relationship wasn’t as advanced as she thought it was.

  20. 40

    It is interesting to note, beyond this issue, how often being supportive gets equated with a willingness to give money.

    If I was in a similar situation I would value encouragement, emotional support and an in interest in what I was trying to do much more than financial assistance.

    I remember how powerful one statement of encouragement from my father was. It overrode all of my own doubts about a risky path I took ( and paid for on my own ) and years of his silence and criticisms about it.

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