assuming he’ll pay: guilty freeloader syndrome

QUESTION FROM A GREEK TRAGEDY READER: I’ve enjoyed your blog for years, and I’d love your opinion on an issue I’m having with a guy I’m dating. We are both in our mid 20’s in professional school. Even though I work summers, money can be a bit tight throughout the school year. My guy has loads of family money and is very generous. (I recognize this as a problem many women would love to have). My main issue is this: when do I assume he will pay? Often he will suggest tickets to games or restaurants that I cannot afford. I will generally say this and then he will get slightly irritated and tell me he was going to pay. I hate to have the same conversation over and over and OVER again, every time he suggests something fun. At the same time, a longer and more in depth conversation about it seems a bit awkward, especially since I will be able to afford these types of activities when we are done with our program. How should I stop feeling like a guilty free loader? straight up advice

Before I take a smack + crack at answering this (and I will), I’ll let others weigh in with their own words of wisdom. Floor’s all yours…

My advice, as promised (written prior to reading comments): The definition of a freeloader is a person who takes advantage of others’ generosity without giving anything in return. I don’t know you, but the fact that you’re even asking this question, at all, tells me, that ain’t you.

Since you’ve already voiced your "What a rockstar idea! I love it! But crapjacks, I can’t afford shite like that, loveass buns" I agree that a formal discussion drawing even more attention to your financial insecurities is a NO. So my advice is twofold:

ONE: Buy a sex book. Do nasty things. Initiate.
Easy feminazi’s. It’s not my go-to advice because of a sense of obligation, or for a way for you to prove your "worth" by making it "worth his while." I bring it up because I believe it will make you feel more powerful. Assertive. More aggressive. Less woebegone. I also think it will boost your confidence and remind you that your worth his time, his doting, his date planning. If you had the means, wouldn’t you just want him to appreciate it and have fun with you? Remember that.

TWO: I wouldn’t dare suggest love coupons.
I’d rather staple my lip to a wall. There is nothing sadder than a book of IOU’s, except perhaps, for air guitar. But planning a picnic date with him, where you do all the planning and surprise him, that’s reciprocation. Because it shows effort. No lengthy talks needed. Show don’t tell. Show him that you appreciate all he does by giving to him in ways you know. If that doesn’t work, go back to my first point, and get a pillow for your knees.

go ahead, askGOT QUESTIONS? NEED ADVICE? If you have questions or need advice on anything from where to eat to how to get over the bastard, just email your question to my advice email address. Nope, I’m not a shrink, but since people keep asking for my opinion, I might as well share it and air it, so everyone else can weigh in too.



  1. If it’s making you feel guilty, or conflicted, or just bringing up these awkward conversations, I would recommend doing things that you can both afford during the school year, so that you can pay your own half if that situation arises. Maybe he’ll take the hint that you’re trying to be equal, and not just free-load, and when he doesn’t want to be special he’ll make it clear that it’s on him (Wait, it’s a mistake to think a guy will take a hint about anything, right?)

    A lot of guys do like to pay for things, it helps them feel like they’re fulfilling their role or whatever, and it also just enables you to do nicer things, go nicer places in your case. But if he keeps responding with irritation to these conversations, it could turn into a source of contention for you guys in the future

  2. Let him pay for everything except for maybe a cab home, an occasional brunch, etc. If you wish to thank him, graciously make him dinner or buy him a small – just thought you would like this – like a book, type item. People are not completely unaware of others’ financial situations, and it sounds like he takes pleasure in taking out his girl.
    If you want to continue to receive his attention, you should take pleasure in having him pay, and just say “thank you.”
    Believe me, if the relationship continues for the very long term, things will “equal out” in the end – whatever that means, and not just monetarily.

  3. I would invite to little things if I were you – whether its the cab ride home or the coffee or the chocolate that he really loves – I’d take care of those small things. You’d be surprised as to how good and satisfied you’ll feel that you’re making your hubby happy and that you’re contributing.

    Assume that he’ll pay for the expensive stuff – whether its tickets or restaurants. Please, don’t mind if he invites. Guys love taking care of their girls and I think you should let lose a little bit and enjoy it. You’re in school, so enjoy the ride completely. The time will come when you’ll get your chance to contribute your share – be it with a mortgage, rent, etc. Trust me.

  4. You are dating this man, so I assume that you think the two of you have a future together. If you are going to build a strong relationship, you need to be able to communicate with him at all times, no matter how awkward it may feel at the moment. Communication is what grows a relationship, and patterns get set early-on. If you don’t start communicating now, it just gets harder in the future. Look at it this way – you are, I assume, frequently naked with this man and having sex with him, which is pretty damned intimate, yet you are afraid to talk to him about who pays for dinner? Here’s what I suggest. The next time he mentions wanting to do something you can’t afford, just say, honey, this is awkward but it seems that we have this little exchange every time you suggest something that I can’t really afford to do while we’re still in school where I say that I can’t afford it and you say you’ll pay and it seems to me that the exchange is frustrating for you and I know it makes me uncomfortable, too. Should I just assume from now on that when you suggest something for the two of us to do together that’s pricey that you are planning to pay for it? Tell him that you want to foot the bill on occasion when things are within your means…and leave it at that. Stop doing the dance and certainly don’t stop going out to do fun things with him because he’s paying – he wants to pay and can afford it and he wants to go out and it sounds like you do, too, so just enjoy it and stop feeling that everything in life needs to be 100% egalitarian at all times – it doesn’t and it very rarely actually is. My fiancee out-earns me by 300% and he pays every time we go out, even tho we split the rent and other household expenses 50/50 and I feel no qualms about it at all. I get to enjoy those things with him, and when we are home, I do all the cooking, for example. As another poster said, things even out – relax. And be happy!

  5. If you are going to feel uncomfortable and awkward every time he brings up doing something you can’t afford right now and you think it might be getting to him to, I would just have the one big awkward conversation and move past it. This way, you both are on the same page and he knows how you feel about not being able to afford certain things at this time. I agree with Molly about allowing him to pay, but doing thoughtful things for him such as making him dinner or buying him a small something as a token of your appreciation. When I first started dating my husband, he paid for everything and I mean everything. I think he enjoyed being able to do this. I would always offer to help out and he never let me but once in a while I paid for a cab or a movie or ice cream, etc.

  6. I agree with Molly – as long as he’s not holding his generosity over your head, he sounds like a really gracious person. I know this isn’t a bf/gf thing, but my husband and I are better off financially than many of our friends. We’re happy to treat and our friends are always offering to “reimburse” in ways they can – babysitting, helping out with our never-ending home improvement projects. I think that if he’s gracious (not grandiose) about being generous, all he really wants is to enjoy time with someone he cares about. Pitch in where you can and enjoy the rest :)

  7. 50/50 is for business relationships.
    Let him pay, it’s something only he, can do.
    Give him blow jobs, it’s something only you, can do.

      1. Clearly you haven’t read most of her comments. It’s always necessary to scrape together a shockingly contrived comment.

        1. Suzanne, it’s not necessary, it’s essential, to break up the monotony that is my life.

          c.j, Carole, i’m blushing…we don’t always cyber agree, but thanks, ladies.

          Fembot, I know you don’t give head, because it’s ‘dirty’, your life partner would appreciate it, giving is better than receiving, sometimes.

  8. I am dating a wonderful man right now who makes a ton more money than me and guess what, I just let him be a man. We talked about it early on and he basically said that he never wants to fight about money with me. He has it, it’s just money to him and that’s that.
    So, while he pays for a ton of really nice things, he was moved to tears when I booked a nice hotel for his birthday weekend and such. I pay things like drinks after dinner, breakfast or so, smaller things and he knows not to give me shit if I take the check when I actually do. I hate cooking, but its a huge joke now when I tell him “I am cooking dinner”…he is a much better cook and actually enjoys it, but that’s me saying “hey love, you have paid dinner a ton these past weeks, let me do something for you.”
    No need to emasculate the man. He wants to pay, let him.

  9. The schtick is old. You’re not shocking, you’re just formulaic. Next.

  10. I went through the same thing when I first met my now fiancée. A few tips from another woman with “poor kid syndrome”

    1. He has the money, let him pay. He wants to pay. He wouldn’t be asking you to do these things if he wasn’t going to pay. Money is not as important to people who have it than it is to people who don’t. Go with the flow and enjoy.

    2. When you can afford something, grab the check or pull out your wallet and pay for it. He’ll think you’re cute.

    3. Get over yourself. This is the best advise I can give. He doesn’t care if you’re poor and can’t afford what he can afford. He wants to hang out with you and will pay the bill. Money can’t buy love, but it will feed you well and give you a good time. Let yourself fall in love and leave the money behind, because that doesn’t cost a thing! It’ll be on you!

    4. Oh yeah, and high fives are always free!

  11. Oh, SK, I think you usually give pretty sage advice but SERIOUSLY? Way to encourage her to avoid learning to talk to him.

  12. When I am forced to do work above my pay grade, I should get oral sex at the end of the day.

  13. I have to admit, my first thought was, if I were to help answer this, blow him. And I don’t know why that’s such a shocking answer on this site. I thought your answer was hilarious and true, Helen. Men don’t want money, they want blow jobs.

    I love, love, love reading this site and thank you all for the great comments today. Cheers a gal up on a rainy day!

  14. I am really laughing at this thread now because it’s basically the advice Stephanie gave. :) I agree with it. “Show” your appreciation in ways he will appreciate!

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