“My Boyfriend is a Cheapskate”

My boyfriend and I have been dating for five years. We do not live together, so when we go to each other’s homes, we will either get groceries to cook or get takeout. When he visits me, I will buy the food ahead of time or order takeout so it’s there when he arrives, footing the bill for the whole thing and not asking for him to pay me back. But when I visit him, he never has any sort of meal planned and, once we do figure out what we are going to do for dinner, we end up splitting the bill or splitting our groceries and paying separately.

He has, on occasion, said, “I’ll buy you lunch/breakfast,” but more often than not his line is, “How do you want to pay for this?” (Which, to me, is him basically setting the situation up so he doesn’t pay for the entire thing because, if my response was “Well, it would be nice if you bought us dinner” or “I bought dinner last time, so it’s your turn,” I become kind of embarrassed and feel like a gold-digger). He doesn’t make a lot of money, and we’ve been together long enough for both of us to know I’m not using him to buy me things, but it’s embarrassing sometimes and frustrating when he conveniently “forgets” that I paid for dinner last time we were together and that it’s his turn to pay now.

It would be really nice if he picked up our bill more often. I know he isn’t rich, and I wouldn’t mind cooking our own meals at home more often if he bought the supplies himself once in a while, but him just plain forgetting that I paid for his meal last time hurts my feelings, especially when we are discussing our next meal and he makes a statement that he has NO intention on picking up the bill. It makes me feel like he isn’t even trying to make the bill-paying fair between us, he’s just hoping we’ll both lose track and I’ll keep paying for both of us, or at least just myself.

How do I bring this up with him? Are there any compromises you could suggest? I’m really nervous that I’m going to sound like a total bitchy gold-digger, but after five years it’s just really unromantic to hear “So, how do you want to pay for this?” every time we eat together. I buy him dinner because he deserves it and it’s nice to treat someone, but when he doesn’t reciprocate as easily, it’s hurtful. — Dating a Cheapskate

Jesus, you’ve been together for five years; that’s MORE than enough time to prove you aren’t a “gold-digger” just because you want your boyfriend to step up and treat you to a meal as often as you treat him. And if you honestly believe he would think you’re a gold-digger simply for pointing out that he doesn’t cover the bill as often as you’d like, you have bigger problems than having a cheapskate for a boyfriend.

But, assuming you’re just feeling awkward about bringing up the topic of money because you aren’t used to discussing finances and bill-splitting and not because your relationship is actually in trouble, I have a few tips I’d suggest (all of which involve COMMUNICATING, so get ready):

1. Decide together on an amount you’re both comfortable spending on dates and groceries (including travel expenses, gas, etc.) every month. Each of you will need to keep track of your own spending and, when you max your budget, you are done treating for the month.

2. Alternate weeks and/or weekends that you treat. Say, you take the first and third week/weekend of each month and he takes the second and fourth. Obviously, this only works if you see each other regularly. You may run into trouble if you take the first and third week of each month and then, huh, he finds a way to only see you the first and third week of every month. Or, when it’s his week to treat, he suddenly only wants to go to McDonald’s. On second thought, if you’re dating a cheapskate like it sounds like you are, this probably isn’t the best option, but I’m including it in case it might work for someone else reading this…

3. Open a joint bank account that you use strictly for relationship finances, like dates, groceries, and vacations. After five years together, it wouldn’t be premature to start merging finances in this kind of way, but I’d only do it if you’re serious about each other and if you think there’s potential for a future together. If you do go this route, you’ll want to decide how much each of you will contribute to the account each month. You will also need to TRUST each other and not have any worry that the other might take all the money in the account and run off to, like, Vegas. This is similar to Option 1, but more advanced.

4. You pay for anything that’s closer to your home and he pays for anything that’s closer to his home. If you live far enough apart and spend an equal amount of time in each other’s neighborhoods/towns/homes, then this could work pretty well (as long as you both have say in what you do/order/eat and it’s not just home town person’s choice all the time). Having dinner at your place? Then you pay for the groceries or takeout. Dinner at his place? He pays.

Of course, if your boyfriend is such a cheap bastard that he never invites you over anymore or he always chooses movie theaters or restaurants or bars that are a mile closer to your place to avoid footing the bill, then obviously this option won’t work so great either. But, honestly, if he’s that sort of fellow, it’s probably best that you learn that as soon as possible so you can MOA if you don’t want to spend your life tied down to a cheap bastard, you know?

5. Go dutch on everything. Split all bills down the middle. Stop paying for your boyfriend. This is annoying and feels sort of juvenile for a couple who has been together so long, but if the other options don’t work for you or if your boyfriend just isn’t responsible or mature enough to deal with merging finances on any level, this is probably your only choice if you don’t want to be stuck paying for 75% of everything.

6. Accept that your boyfriend is cheap, decide whether that’s a deal-breaker for you or not, and proceed accordingly. If it isn’t a deal-breaker and you’re willing to put up with having a cheapskate boyfriend, focus on the qualities he brings to your relationship. Abundance and generosity come in many packages and just because someone isn’t abundant in wealth or financially generous doesn’t mean he isn’t abundant and generous in other ways. But if those ways aren’t enough for you or if being cheap is a deal-breaker and there’s a chance your boyfriend’s just cheap, then figure that out now and move on already, because five years is already enough time to spend with someone you don’t have a future with.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.


  1. lets_be_honest says:

    Just say “I think its your turn” next time he asks how you want to handle paying for it.

    1. Exactly. And, if after 5 years, you can’t do that, then you’ve got bigger problems than who is paying for dinner.

      1. lets_be_honest says:

        I understand it money talks being awkward. Frankly, I’d rather just pay the bill for someone who made an issue of paying it…once. And then I’d just not eat out with them again. But saying ‘its your turn’ to your boyfriend of 5 years should not be awkward at all.
        It is funny, as rosie posie pointed out, that SHE is concerned about looking greedy when she apparently pays for almost everything already.

    2. That’s a good opening for a discussion too! “How are we paying?” “It’s your turn.” He either goes with it and now you’ve got a new “routine” (taking turns), OR he scoffs and now you can talk about it.

      1. Yeah, I mean, I’ll say that even with groups of friends— “how are we going this?” & usually I just mean, okay, is it all going on a card? Are we getting separate checks? Am I covering it all, since I know you’re broke? Are you gonna cover it, because I just spent all my money on drinks? I don’t know, I feel like this should have been worked out WAY WAY before the 5 -year mark. If this has been their “routine” for that long, there must be a reason it was never brought up?

      2. She says he doesn’t make much, but doesn’t mention herself. Maybe she makes a lot more and so he assumes she’ll foot the bill more?

      3. Yeah, that’s what I’m thinking (I touched on it a bit below, but my thoughts came out kind of scattered). And then, if this IS the case, I wonder why she’s attempting to flip the script ~now~ after all this time? It seems like maybe she’s just gotten frustrated with this being the status quo, but it can’t really change TOO too much, if he actually doesn’t even make enough money to treat her. That’s why I kind of think this is the superficial issue, with the real issue being something like, “I’m unsatisfied with my boyfriend’s income”?

      4. I think you may be onto something there…

      5. Ooh! And that’s why she’s afraid of coming off as gold-diggery – she can afford it, he can’t, but she still wants to be “treated.”

      6. lets_be_honest says:

        I’d assume you’re right about their finances, however, no one should just assume someone else will always pay for them.

      7. Oh for sure. I’m just speculating as to how this came about.

    3. feelingroovy says:

      For real. My ex would say things like “why don’t you pay for the movie since I got dinner?” and I never once thought it was a cheap or rude suggestion.

  2. Avatar photo rosie posie says:

    I know the LW is worried about sounding like a gold digger but she shouldn’t be. It sounds like her boyfriend is the gold digger in this relationship.

  3. Avatar photo GatorGirl says:

    Wendy your first sentence is exactly what I was thinking! 5 years and this hasn’t been discussed/resolved? wtf?

    1. I got the feeling that they are fairly young. Those kinds of discussions are much more awkward if you’ve never had them with a partner before.

      1. Avatar photo GatorGirl says:

        I definitely agree, it’s harder with less experience (I got the super young vibe too). But come on lady, stand up for yourself.

  4. Why is it so hard to just say, “Hey can you pick up some groceries?” Or “Can you get the check this time? I bought the last 2 meals out.”

    I feel like so many LWs avoid simply talking to their partners, and then make everything into this huge thing where they have to sit down and have a full discussion about something, when it really doesn’t need to be that hard.

    1. Avatar photo GatorGirl says:

      Yes! People blow things TOTALLY out of proportion. Being worried you’ll look like a gold digger because you want to split expenses?? Not everything needs to be a “come to Jesus” talk. Some things are just talks.

    2. Frankly, I would also ask him to plan meals and pick up groceries because of the work this entails. It’s not cool if she always has dinner ready and he never does…

  5. kerrycontrary says:

    I would show him this letter. I think it accurately explains the situation and lets him know how you feel. Plus after 5 years you should be able to be brutally honest about stuff like money. It’s ok to say “my bank account is running low until I get paid next week” or “I just bought $40 worth of groceries to cook for you, can you pay?”. It’s only uncomfortable if you make it so.

  6. This is one of those situations where the LW desperately wants to make an awkward situation non-awkward. Yes, if you bring this up, it might be a little awkward because it will be obvious that you’ve noticed what he’s doing. You can’t tell him “you’ve really got to pay once in a while” without implying that he hasn’t paid enough in the past (and he clearly hasn’t!).
    Personally I would choose the “my place, my treat, your place, your treat” route and alternate when you go out. It’s easier than trying to split everything 50-50. A true cheapskate will then try to buy super cheap groceries or treat to McDo, but at least then it will be obvious that they are deciding to be this way.

    1. seriously, so many good things would happen if people could deal with being a little embarrassed sometimes…

  7. LW, I don’t think you know the definition of Gold Digger.

  8. honestly, i think this is on you. him saying “how are we going to pay for this?” isnt that weird. especially after 5 years, the romance part of wining and dining is a little…. gone? not that it shouldnt happen or anything, but after all that time i feel like its sort of more like the partner who still buys a birthday present using “their” money. the gesture still counts, absolutely, but the reality is that you both know where the finances are, how much the present cost, ect. so i dont think its that weird that he says that. i say that all the time, i think. so its now on you, then, to speak up if its his turn and say “you got it, right?”. dont let feminist-guilt or whatever it is stop you from saying those things. stand up for yourself and for fairness. if you guys have agreed to share these expenses, which would include actually talking to each other about it and agreeing to something, then do that.

    i think wendy’s suggestions are good ones, though. but at the core of it, YOU need to start stepping up, speaking up, and following through.

    also, you might want to look at this situation from outside of your own perspective. you are giving yourself all of the credit for always picking up the tab, always bending to the “how are we going to pay for this?” question out of i am assuming what you believe is your duty as a “good” partner. if you shift your perspective on it, you might see that he either doesnt think this a big deal at all and he doesnt give you the same credit you are giving yourself, and that he doesnt feel a duty to buy stuff for people out of love. that doesnt mean what your or he is doing is bad or wrong, but it means that as long as you keep this perspective you have, you will just keep banging you head against a wall.

    1. lets_be_honest says:

      If he doesn’t give her “credit” for paying for almost all his meals when they are together, he’s a selfish jerk, imo. This isn’t her saying ‘I do all these cute little things for him’ not realizing he may not care about those cute little things.
      When someone takes you out for dinner, you appreciate it and be grateful for it, not expect it or not “give credit” for it. That’s just common decency.

      1. im just saying, he might not see this as some big deal that you have to take into account- like thats how my life was growing up. you just never took that into account. someone just paid, it didnt matter who, it just happened and no one cared.

        and im sorry but she does kind of sound like a martyr with always paying when he asks how they want to pay for things. come on. there is no gun to her head.

      2. lets_be_honest says:

        But didn’t you at least say thanks for dinner?
        Idk, if someone pays for me for anything, I acknowledge and appreciate it and try to return the favor. Money doesn’t grow on trees.

        I agree there’s no gun to her head though. However, I couldn’t stand having to deal with me paying all the time and my boyfriend playing coy trying to get me to pay, never offering, etc. If he can’t afford his own meals, don’t go out to eat or be sure your girlfriend is willing to pay every time, not ask if she can when the bill comes.

      3. Oh well of course- not keeping tally of who paid when doesn’t negate being thankful.

        Ha, yes, all that is true, but that falls under the “communicate effectively” umbrella, which these two are sadly not even aware that it exists, apparently. Him for not establishing something *if* he does have money problems and her for never speaking up and letting resentment grow.

      4. Also, she is shooting herself in the foot again by never asking him “how they are going to pay for this” when she plans ahead about meals. This LW is a sucker for punishment!

      5. lets_be_honest says:

        Yup. My guess is she is just uncomfortable talking money (understandable to a degree) and got the feminist-guilt (as you said) drilled into her head a little too hard. She should just say its your turn, or he should just say you make more so its either you pay or we never go out anymore.
        Really though, yuck. For him to never ask beforehand for her to pay is just yuck. So he is more yuck than she. haha.

      6. Well, I mean, you can’t really hold that against him when nothing is brought up that his partner is unhappy though. And anyway, there are lots of couples where one out earns the other and so pays for entertainment/eating out. Or couples where there is only one income and one person pays for literally everything.

      7. lets_be_honest says:

        So just because she hasn’t said she’s upset, he should go about assuming she will pay for everything all the time? That makes little sense to me. They have agreed to nothing, she never said ‘hunny, i make more so i’ll always pay’ and he’s never asked ‘can you always pay since you make more.’ That’s a pretty obnoxious assumption to make on his part.

        The other couples you talk about likely HAVE addressed the issue and mutually agreed upon something. Not assumed anything.

  9. Hold the phone – when discussing your next meal he tells you he has NO intention of picking up the bill?! Then, I guess he can just watch you eat – from outside the restaurant.

  10. I like the “whoever’s house we’re closer to, pays” rule. But honestly, yeah, just be like, “Why don’t you get this, this time?” If that’s awkward to say after 5 years of apparently not saying anything, then maybe extend the sentiment so it’s not so casual: “Hey, I realize I’ve been paying a lot, do you mind picking this up?” Or even a white lie, if that helps you ease into the conversation— “my check hasn’t gone through, can you splurge this once?” And later, if you want to add, “Look, I actually pay for us most of the time, do you want to rework things so it’s more balanced?”

    After 5 years, you should be able to have this conversation. Maybe he really is cheap, or maybe he’s just not keeping track of things. You honestly are making it easy for him to NOT pay, you know? Like, maybe don’t buy cooking supplies/ingredients next time, & just ask him to pick some up on the way? Or BEFORE the check comes when you’re out, say, “Listen, it’s your turn”— I have NO idea why you would think that makes you seem gold-digger-ish? Especially since, by saying YOUR TURN, it’s a reminder that *you* paid last time (“gold-diggers” wouldn’t have even HAD a last time, you know?)

    I don’t know, what was he like in the courting stages? It is just established that he makes less money than you, so he assumes you’ll pay? And you’re getting recently annoyed by it? I feel like maybe there’s more to the story…

    1. Also, my other guess is that the guy just actually doesn’t have any extra money? Maybe ~that’s~ why the cat has caught this LW’s tongue? (Like… maybe their communication is fine, & she just knows NOT to say “your turn today!” because she knows it’s literally impossible for him to pay? And she’s kind of just wishing he saved up a chunk one day in order to be like, “My treat!!!” but since he’s like, “How do we split this?” that’s her cue to know he doesn’t even have money to cover?)

      1. I think that’s sort of too much to assume. And if he can’t even pay to have groceries at his home, then I think that’s way different than a person who can’t afford to buy a fancy meal out.

    2. i agree, there has to be more to this story. i just refuse to believe someone would be this scared and timid after 5 years with someone else.

  11. What’s wrong with just saying, “You aren’t pulling your weight here”? If I did this to M while we were dating, she would probably have said, “Why don’t you pick up a check once in a while, ya cheap bastard.” If being direct would be a problem after 5 years, then your deal is broken.

  12. Bittergaymark says:

    Maybe you two simply eat out too much. If you’re both THIS fucking broke cool it with the wining and dining. Seriously. And if you make more money than him — well, welcome to equality. God knows women pull this sort of shit all the time on their boyfriends who make more money… Turn about is fair play. Or should be. But clearly, double standards persist…

    1. kerrycontrary says:

      It still costs money to purchase ingredients to make food at home. So even if they eat at home, it sounds like she’d always been the one paying at the grocery store.

    2. I’d love to hear if she makes a lot more than him. If that’s the case, then it would be even weirder for her to be afraid that she could be perceived as a gold digger… I can’t really square that with her earning a lot more than him.

    3. My boyfriend and I always find groceries for a meal to be equally or more expensive as eating out. We don’t live together and therefore are not buying groceries for a household, so there’s no stockpile of anything. Even if you’re only using half a cup of sugar you still have to go out and buy a whole bag. Replace sugar with every single ingredient in the meal you’re making.

    4. If she’s buying all the food, then that’s not equality. Regardless of double standards.

  13. Avatar photo Addie Pray says:

    This may be a little commie of me, but, I have an idea for my own country if I ever get one, and doesn’t this sound dreamy: everyone pays a fee to the government each month relating to how many times they want to go out to dinner. Then when you go to dinner, you just go, and you don’t pay for anything, and the restaurant let’s the government know you’ve cashed in one of your dinners out. That way there is NO money exchange ever at a restaurant or bar. NO MORE “HOW SHOULD WE SPLIT THE BILL?” QUESTIONS! Oh, same thing with bars – you just let the government know how many bar tabs you’d like a month. Or something. And there would be no need for money EVER because the bar/restaurant could just scan our eyeballs and it would link to our profile on file with the government.

    I’m still working out the rules of this new government idea. Never ever having to deal with money issues when dating may be worth all this government intervention, no? I mean, I’m still stressing out about the fact that last week when I went on a first date with MG’s friend, he paid for the whole bill. Maybe this is a little drastic but come on, my country would be so fun. You’d all be invited. And all restaurants would be required to serve breakfast 24-7. None of this “oh we stopped serving egg mcmuffins at 10:30 am” honky bullshit.

    1. Addie, you are such a commie. Although, I’m gonna be honest, I could get behind the whole restaurants being forced to serve breakfast 24/7 thing.

    2. Avatar photo lemongrass says:

      I think you just want to live in an all inclusive resort. No shame in that.

      1. Avatar photo Addie Pray says:

        OMG that’s it. You nailed it. I would’ve spent WAY too much time planning this when all I needed to do was book a trip to Cancun!

      2. Avatar photo Addie Pray says:

        Basically, my new country is going to be an ill inclusive country. I can’t wait!!!! But I’ll make sure we still need money for something so I can get my picture on it.

      3. I’m just picturing people walking around city streets all day with those blue plastic bracelets you get all inclusive resorts, getting wasted all day because there are no limits and nothing they have to pay. Whose gonna sponsor it?

      4. That sounds wonderful. Will someone sponsor ME??

      5. Avatar photo lemongrass says:

        Ill inclusive, while may look like a typo, is really the appropriate term for how you feel while there. At least in the mornings.

    3. What about like in France where your employer has to provide you with a lunch ? Some of them have a cafeteria, but a lot of them give “gift-certificate” that you can exchange for meals in restaurants. And then smart people pack their own lunch, accumulate the restaurant certificates, then go on a big night out at the end of the week. No bid deal, it’s the company’s money, not yours.

      1. Avatar photo Addie Pray says:

        Oh I loved those tickets when I was in France.

    1. Hah I THOUGHT this sounded familiar.

      1. I like the specifically tailored tone of both letters. This LW knows what they’re doing and hooked both Wendy and Coquette

  14. Generosity is such an underrated virtue. Of course, the amount of money you make doesn’t make you a generous person. It’s a quality of mind that’s precious and rare in this world. Quibbling over a check is such an unattractive thing — even if you’ve been together 5 years.

  15. landygirl says:

    LW, if you can’t talk to him about this then you have a bigger issue than money. I’m not sure why you think asking your BF to pay for a meal would make you a gold digger? Who put that notion in your head? Talk to him and in the meantime, stop paying for him and pay only for yourself. Next time he comes over, don’t buy groceries or have take out ready, wait until he gets there and figure out what you want to do then split the cost. He won’t change but you certainly can.

  16. I think this is a problem more of feeling unappreciated than anything else. If he just said “Hey, I know you pay for more stuff, but I am really broke and I will help in this other way” she would be ok with it. Or, if he offered to pay something when they are at her house. I’m getting a vibe like the LW feels she’s been taken advantage on, but doesn’t want to sound gold-diggery if she stands up for herself?

    I think this is one of those things where if you don’t talk about it, you are going to really resent the other person, and you will be getting angrier and angrier. You have to either let this go and stop waiting for him to offer to pay for stuff, or have a clear discussion about everything to see where you stand.

  17. Can I just say that women need to stop being so hard on themselves and calling themselves “gold diggers” when they’ve been with a man for 5 years and *gasp* would like to be treated to a dinner? There’s nothing gold-digging about that. Why is it so hard to ask to be treated a certain way?

    Also, at the end of the day, it’s just fucking money. It’s so unsexy to be upset about who pays for dinner. At the end of our lives, I hope to god people aren’t thinking, “Oh, I wish my girlfriend paid more when we went out to eat.” But I know I might regret being with a person who was cheap prick.

    1. landygirl says:

      There are a lot of bitter guys out there that think all women are nothing but gold diggers and they aren’t afraid to express it.

      1. Bittergaymark says:

        Eh.., That’s because they often have good reason. Take yesterday’s letter and a good many of the responses. “Hi. I think my BF of a few months should split tbe rent with me 50/50 now that he lives with me AND my four kids…” •rolling eyes.

      2. landygirl says:

        No, he didn’t pay rent at all and barely contributed to the household. That isn’t being a gold digger unless you are calling him the gold digger.

      3. Bittergaymark says:

        Well, does he get paid for childcare? 😉

      4. landygirl says:

        I just hope that they don’t reproduce with each other.

      5. I’ve had guys mooch money off me before. Why don’t we call them golddiggers? Is there a word for men who mooch off women for money? If there’s not, one should be created.
        Women who are clearly not golddiggers (like this LW) should not be shaming themselves, acting like they are.

  18. This is why my boyfriend and I split everything down the middle, always. Even after 3 years. We always just get one bill and just splt the payment between 2 debit cards. It works for us!

    1. lets_be_honest says:

      Seriously! Its not super romantic, but its the easiest thing in the world to do.

      1. Yep, especially because we eat out at a variety of price ranges. One weekend dinner might be $20, the next its $100. So it wouldn’t be fair to trade off on weekends. I dunno, I like our system.

    2. FossilChick says:

      I think this is the ONLY solution that will fix the LW’s problem quickly. Obviously they need to communicate about finances, but if the BF is okay with going Dutch when he might be expected to pick up the tab, why not just do that all the time?

  19. Well, not to totally blame the LW but he’s cheap because you have set it up that way over FIVE YEARS and haven’t stopped it. Not to quote Oprah but one thing she said that I always think about it is “you teach people how to treat you.” Time to say, I’m over this!

  20. sarolabelle says:

    I’m glad I’m married and everything is shared. I could never date long term like that.

    I paid for dinner the other night with our shared credit card and he said “thanks for paying babe”…..

  21. Lily in NYC says:

    Please think about if this is how you want to live your life. Because an ingrained cheapskate rarely changes. My sister married one and honestly, I don’t think she would do it all over again if she could go back in time. Thank god she makes 3x his salary or it would be a constant fight (I know, I know, they are married and they share everything but my point is that I think her husband would put up a bigger fight about spending if he didn’t feel weird about making so much less). And believe me, my sister is not the type to spend money on petty crap. At least the one thing he doesn’t act cheap about is their daughter (but that’s another story – the man can’t so no to her). Sigh, it would be nice if his main criteria for choosing a restaurant is if they have free drink refills.

    1. Bittergaymark says:

      Honestly. If she’s so fucking obsessed with dining extravantly she should gladly pay for it. I never expected my lovers to pay for my scubadiving trips…

  22. quixoticbeatnik says:

    Wendy’s advice is spot-on! When I was with my ex, we usually split the bill down the middle but every once in a while I would treat and every once in a while he would treat. That way it felt a little bit more special. LW, if the arrangement you have now isn’t working out for you, then change it. You have to tell him how you feel and that you want to change things. Are you planning on marrying this guy? This is just the beginning of money and finance talks. Before you get married/once you get married you will have to figure out the finances for a shared household, who will pay for what bills and so on and so forth. You’ve been together five years, if you’ve talked marriage then for the LOVE OF GOD you also need to have a serious finance discussion. Do not put this off.

    Also, why does he not have very much money? Just from the letter it kind of sounds like he might not have a very demanding job. He seems content to kind of skate by in life and maybe mooch off of you – or he thinks you will be around to take care of the money stuff. That’s just the general impression that I get from the letter. If that’s the case, then I would take a serious look at your relationship and what you want from the relationship – what kind of a person you want to be with. I don’t really care how much money a guy makes, but one of my big things that I look for in a guy is ambition – a desire to grow and learn. I think you kind of want that too. I think you are looking for more equality in your relationship, and there isn’t anything wrong with that. You’re not a gold-digger. If you were a gold-digger you would be demanding that he pay for everything. You’re doing the EXACT opposite of that – he’s the one that seems like a gold-digger here.

    Maybe I am making a lot of assumptions and generalizations here, but I just get the feeling that there is more going on here than just money issues. I think you may not be happy with the relationship anymore and the money issue is just a way to avoid that. The money issue can be resolved fairly easily I think, but deeper relationship issues require more time and effort. You can talk to him about this – you can communicate with him. Don’t put it off.

  23. Apropos of nothing, I just realized the dollar bill origami thing at the top is a heart, not an airplane. Has it been a heart all along?

  24. Sue Jones says:

    There was a period in my relationship when my now husband would “forget” to bring his wallet into a store/restaurant, etc. At first I just covered it. But after enough discussions about money and his lack of at the time, I finally just started looking at him and would say “Really??? Go and get it. I’ll wait!” And this “I’ll take you out to dinner” and then asking you to pay is bullshit. I would say very clearly “You said you would pay for this. I left my wallet in the car…” We have worked it out, but my husband was a bit of a cheapskate early on in our relationship… Maybe a lot of men are these days.

    1. Sue, thanks for this! It made me feel better. My new boyfriend (of less than a month) is already talking and worrying about finances. I’m glad I’m not the only one who has experienced this and that it’s something you and your husband worked through!

  25. WWS! This is a great opportunity for you to increase your communication skills and get comfortable talking about money. This will not be your last conversation about money (I guarantee it!) so it’s best to start now.

  26. i laughed reading this letter because it totally describes this guy i was dating….he would never pay (for anything)….the best was when he came over to my place and i ordered a pizza and some wings (which i paid for)….he served the pizza and made a point of saying i could have a “small” piece….i put the leftovers in the fridge and as he was leaving he goes into the fridge and grabs the box of pizza and the container of wings that were left over! wtf? like its not bad enough you didn’t pay for the pizza, but then you gotta take my leftovers home without asking! i ended up finding out later that he had a son with another woman who he didn’t pay child support for (ugh! nothing worse than a dead beat dad!)….long story short we are no longer dating!

  27. WWS! I love her ideas (especially 2, I do something similar to that). If they do have very different income levels and he’s embarrassed about that, perhaps he could pay for meals that cost less, so that he’s treating her every so often. I’m not saying it works in every situation, but knowing that he’s treating her more of the time as opposed to with equal amounts of money might make the LW feel better about the situation.

    But mostly I wanted to respond to the commenters that were incredulous that this hasn’t come up in 5 years. They do seem pretty young, so maybe paying for meals they have together is a new thing. For instance, in college, a lot of people eat at the dorms, so that could be up to 4 years of mostly eating meals they couldn’t have paid for. Second, if they’ve done distance, that’s not a lot of meals to share either. Finances, particularly about meals, never really came up while I was long distance with my boyfriend, so this could be a problem that’s quite new.

  28. As a man, I have almost always paid for dinner out. And never once considered calling my lady “cheap”.

    She would cook dinner at home, on her dime from her refrigerator.

    If I was low on money, and she wanted to go out for dinner, I would just explain “I am low on money, and she would either offer to pay, or we ate something less expensive.

    All this young lady has to say is “I am short on money to eat out, but I will cook. Then he can offer, or not, and see where it goes from there.

    It does not always require some long winded explanation or relationship discussion. Just say you have a budget, and have reached the limit for the week. Either he decides to “treat” or not, and decide from there.

  29. So, this is another situation where a person thinks that by treating their partner how they want to be treated, their partner will automatically treat them that way. But it’s not how it works. I’m not saying you buy food for him because you want him to buy food for you, but you base a lot of this on the idea that YOU do this for HIM, and he won’t reciprocate, when in reality, the point is just that he doesn’t ever buy the food. The problem with this is that a lot of people, often men, will assume that you did a thing just because you wanted to, and that it doesn’t necessarily indicate what you want them to do. Because a lot of people, like men, assume that if you wanted them to do something, you’d communicate that.

    I think part of the issue is that you seem to think that you only deserve him to do something nice for you if you’ve “earned” it. You seem to feel like you need to justify wanted him to pay an equal share. You’re worried that you’re going to appear to be a gold digger because you want to pay for food equally? Or that you’ll be a bitch for bringing it up? Honestly, if you partner thinks you’re a bitchy gold digger for expressing your needs or for wanting him to pay for food sometimes, then I don’t think that’s the relationship for you.

    So, just tell him that you want to share food costs more equally. It may be that instead of you taking turns treating, you guys split all the meals (since you haven’t asked your boyfriend how he prefers it — splitting or alternating), or maybe you do take turns. But regardless, if doing a nice thing for your partner makes you resent them, then don’t do that thing anymore. It’s not fair to resent someone for something that YOU are doing without their suggestion.

  30. I’ve experienced a little of this with my new boyfriend and it’s interesting to read all of your responses. Unlike the LW, we have only been dating a few weeks, but money has already come up. He lives about 1.5 hours from me and always wants to drive to see me because there’s nothing to do in the town where he lives, but I live in a major city in our state where there are lots of things to do for dates. Of the four weeks we’ve been together, I’ve cooked for him 3 out of those 4, because he has expressed angst about the money it costs in gas to drive to my city. Last week, I sent him home with 3-4 days worth of food for meals during the week, too.

    I am grateful that he drives to see me and am more than happy to cook for him, but once in awhile I would love if he would take me out to lunch, because Sunday is our day together and sometimes I’d just prefer not to cook. He knows I’m more than willing to help out, and the times we have gone out we have either gone back and forth on treating or have paid separately. He’s been very open to my needs and interested in healthy communication so far, so I’ll have to broach this subject with him sometime soon. We’ll see how we go – hopefully the conversation will go well.

    Ah, dating…so much fun! Haha.

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