Should I just shut up and let him pay?

Guest post by March Adams
By: Robert S. DonovanCC BY 2.0

Recently I started seeing a guy that I had merely been sleeping with in a friends-with-benefits kind of way. The situation worked delightfully well for about half a year, but then we decided to take it a step further and start dating.

Now, maybe it’s because, save for a handful of first and second dates, I’ve been single for five years and used to making my own way. Maybe it’s because I’m inching towards my mid-thirties and my perspective has changed. Maybe it’s because he and I work in the same field and, therefore, the same income bracket and I have a rough idea of how much he makes. Or maybe it’s just my strong sense of independence and feminist ideals.

Whatever it is, I suddenly find myself in a position where after half a decade of buying my own dinners and buying my own drinks, I have a man buying them for me. And having a man buying them for me feels, well, odd.

Not just odd but a little bit uncomfortable as well if I’m being completely honest.

I’m uncomfortable even when I thank him, and he says he’s more than happy to do it, and I believe him. Even when I know he wouldn’t be buying me dinner, and concert tickets, and surprising me with fancy “just because” cupcakes unless he really wanted to because — let’s be honest — the guy went from guaranteed no-strings attached sex, to dating and feelings and all the strings attached to relationships, including the financial aspect. (But, of course, also the sex as well.) Even taking all of that into consideration, I’m still coming to terms with this new arrangement.

Not to say that I always adhere to this. I’ve taken the check out of his hands and told him it was on me. We’ve gone Dutch. I’ve also surprised him with fancy just because cupcakes.

Obviously he wants to pay and is happy to pay. If he didn’t, he wouldn’t keep suggesting dates that require money. But the offbeat, long-term single woman inside of me resists and rebels.

I’ve spent most of my adult life paying my own way and it’s hard to suddenly accept that someone now wants to do it for me and on a regular basis.

How do other couples do it? Do your partners really not care, or not see it as a burden? Am I over-thinking this?

Comments on Should I just shut up and let him pay?

  1. Hmm, this is tougher than it sounds. In general I think, unless one partner in a relationship is significantly financially worse off, there should be relative half-and-half sharing of money matters, including the cost of dates. But, on the other hand, I get how sometimes it’s nice to buy someone a present or a dinner sometimes.

    Generally, with my partner, we mix it up. Sometimes we split the cost, sometimes he pays, sometimes I pay. I think this works well, because you get the “datiness” of buying someone dinner, and both parties get the joys of both giving and receiving.

    Maybe it doesn’t feel “romantic” enough to him somehow if you split your costs, as though you were still friends. But it might feel romantic if you said, “I’m taking you out tonight, because you’ve been so great to me this week – you pick the place, it’s my treat.”

    • I like the idea of mixing it up. I’m in a poly relationship and he currently has more dating expenses in addition to regular living expenses. We agreed early on that we would pay for our own meals unless the other offered to pay (there would be no “arguing” if the other offered). We’ve adopted the same for bigger date items….recently he paid for museum tickets, we split movie tickets, I paid for a big fancy homemade dinner, he’s buying off broadway tix for my b-day.

      I think it’s all about communicating and ensuring you’re on the same page from the onset.

      • Other dating expenses in poly relationships is not something I even considered here! Great point. It wouldn’t be fair if someone felt unfairly burdened.

    • Oh, I love the idea of making it an advanced plan. Usually I pick up the check at the end of the dinner or whatever, but letting him know that it’s something special and on me going in is different. Thanks for the suggestion!

  2. When I started dating my now husband we just went back and forth. I’d pay for one date, he’d pay for the next -as long as it was something “normal” like dinner, a movie, bowling etc. If we got into expensive things like concerts or trips together, We’d split it down the middle, or one of us would pay initially, and the other would pay that person back their half later.

    • this is what we did at the start, and 8 years later we still do this. hell, we do it with groceries and everything else, too. it just works out that way.

  3. I’m not getting the impression you’ve had a real discussion about this, as of yet. That would be the first step, if you’ve not already taken it.

    I think there’s a part of the social DNA, at least in Western countries, where paying for your lady-date is expected part of being a gentleman and a way to show affection. It’s a bit old, in my opinion, but certainly not beyond a discussion.

    He may not be totally comfortable going dutch all the time, but I think there’s room for compromise here. Whether it’s occasionally splitting, doing an every-other date pay scheme or (since you mentioned a financial melding) a co-account for dates that you both contribute equal parts to, but allows him the “face” of paying for you in public (if that’s amenable to you both, of course).

    I think you also need to take a step back and think about what it is you would like to have and what would be a reasonable compromise to the situation. I don’t think it’s insurmountable, but I think a good conversation about it when money is not around — so one of the times you do something free, or are hanging out, or if you go on walks together or something like that — would be a good time to strike it up as it limits both of you from getting really defensive.

    • My hubby was raised in a conservative family (dad works, mom stays at home) AND has always worked in a conservative workplace (the police, where misogyny is RAMPANT). Luckily there were women before me that had already schooled him and made him more open-minded (though he also learned a lot from me). So I let him pay the first one or two dates, then sprung for the check, say “hey, we BOTH had fun, we both should pay” (or something like that). Since we´re both more frugal than most, we don´t really do many money-dates, but will treat the “date” item the same as the “grocery” item in our joint “running tab/monthly budget”. At the restaurant/whatever, we will take turns actually dishing out the money (even though we both know that we are really BOTH paying). We also “treat” each other out (“I´m taking you out to dinner tonight because of WHATEVER”). Because sometimes/ with some crowds it´s important to him to “save face” (though we both know it´s actually BS), I will quietly slip him the cash to pay for both of us (which I did at our last “group date”), our I´ll give him a cue and hand the money over while we are BOTH looking at receiver (aka, I “collected” the cash, but it´s obviously from BOTH of us). What is also “fun” for us is to bet on dinner out so OF COURSE I´m going to pay if I lost (I will admit to sometimes betting just to take him out! ; ) LOL!) Oh! and the “pay for your lady-date” thing wouldn´t help LGBT people, just saying! 😀

  4. When my guy and I were going out, we did the “whoever plans the date, pays” thing. So when he joined me for my weekly swing dancing group, I paid our entry fee and bought an appetizer and drinks afterward. When he asked me to see a movie, he got the tickets and popcorn. I also felt uncomfortable letting him pay for everything, so I tried to make sure that at least some of our dates were things I planned for him. But that only works if it suits your relationship dynamic for you to take on some of the planning (and if your guy doesn’t then expect you to take on ALL of the planning).

    • I think this is the standard etiquette nowadays. Whoever invites, pays. You can invite to fancy dinner or hikes or milkshakes, whatever your comfortable with (both socially and financially).
      In my longer term relationship, we still kind of do this, “Do you want to get dinner? I can pay” or “I’m hungry. I can buy pizza if you want” and we sort of alternate this

  5. I hate being payed for. If it was still a friends with benefits deal then maybe I would let it slide but if this is a guy that you could really see a future with then I would say something. For me that would sour a relationship very quickly if it wasn’t addressed (and if he didn’t listen then that would be a problem for me).

    I do understand though that splitting the bill can feel unromantic or cheep for some people-I had a bf a while ago that hated the idea. He actually did have more money than me at the time but it still felt…well, uncomfortable, like you say to let him pay all the time. We came up with a deal that we took it in turns to organise dates. He payed for his days and I payed for mine. It was nicer than splitting the bill and we both felt that we got value out of it- he spent more money but I spent more time and effort organising things.

  6. If he suggests he’s happy to pay for your dates, why not suggest you’d be happy to pay for some dates too? This way, you can split the costs by alternating the dates each of you pay, without making him feel bad and still maintaining your own sense of independence.

    I used to insist about always going Dutch at the beginning of our relationship, for all kind of reasons – the main being that on first dates, I would not allow to feel pressured to make out just because he paid for something. After some time, I allowed myself to be treated from time to time, and he’ll gladly accept that I treat him sometimes as well. Though now, most of the time, we use our joint account to pay for our dates 😉

    • “feel pressured to make out just because he paid for something”

      This is such a great point. Buying dinner for someone NEVER “buys” you anything else. You should never feel pressured to do anything you don’t want to, and certainly not feel obligated to do anything if someone spent money on you. (On the other hand, if you want to, go for it!)

    • I hated dating because of this reason! I always wanted to go Dutch on first dates and early dates, but when I was single I was so broke it ain’t no joke. Eventually, I ended up telling people that I wouldn’t mind going on a date, but that I had no funds to contribute and would offer suggestions for free things we could do. They always offered to pay (who am I to turn down a free meal?!), but it felt better being honest before the date AND providing alternatives beforehand.

  7. My husband and I have always taken turns paying for dates, more or less alternating every time unless one of us wants to do something really expensive in which case the person who suggested it usually pays. I don’t think there was even a conversation about this, just my saying “Let me get this one” a couple of dates in and thereafter until it became habit. When we travel we do something like have one of us pay for lunch and the other pay for dinner one day and then switch who pays for which meal the next since dinner will usually be more expensive. We both get to treat each other and we know it evens out over the long run.

  8. When it comes to going out for dinner my partner and I switch-off on paying: one time he will pay, and the next time we go out it’s my turn. That way we both get to feel like we’re treating each other, and it’s a lot easier than splitting the bill.

  9. Hubs and I still split dates (that are not special events) out of our personal accounts. When we were dating we took turns paying by who organized the date or just alternated if it was something we did regularly.

    But we talked about it and tried to make money (or lack of) not a big deal in our relationship.

  10. Whoever you ask will have a different take on whether it’s right or wrong for one person to always pay and more specifically what this means when the payer is male and the paid for female. This is about what it makes you feel and if it makes you uncomfortable then talk about it.

    For me it’s about equality and there is no denying that if one person always pays that there is an imbalance and powerwise it is in favour of the payer. However in relationships things just aren’t equal (incomes especially)and it takes careful negotiation between two willing partners to balance things out. For example my wife earns twice what do and therefore pays more rent, but food and bills are equal. If I insisted on splitting the rent then we would have to live somewhere else. Occasionally it makes me feel weird, if I really dwell on it I can squeeze out a feeling of slight shame that she pays more than me. However it makes total sense to do it this way, I’d do it in a heartbeat the other way around. Getting to this arrangement though was tricky and took negotiation.

    I find being paid for can be potentially disempowering (not saying it universally is) if the payer has not negotiated it with me, it sounds like there is an assumption going on in your situation that irks you. This is the time to tackle it because how you are able to deal with it together will tell you a lot about your potential together. Your guy is not in the wrong and so should not be told off but some kind of discussion, preferably before the point of anyone paying for anything sounds wise. It’s always scary the first time you have a discussion with someone you are seeing about how you want to handle things together but it’s kind of the first big couple moment. Good luck!

    • I fully agree with this comment! I’ve always found the “who should pay” dynamic to make me very uncomfortable, and find that it can create an unease no matter who is doing more of the paying. For example, in my first serious relationship I either paid for myself or paid for both of us for almost everything: I paid for meals, drinks, movies, all the travel expenses to visit him, everything. I paid for a nice steak dinner on his birthday each year, and each year on mine he made me pay for him yet again.

      In contrast, my current boyfriend and I split costs. Before I even asked him out we had discussed my ambivalent feelings towards paying for dates, and he took notes: I like the offer of being paid for, but I like to pay for myself or pick up the full tab as well. I like things to feel even, I like to feel like someone isn’t going to use the ol’ “I paid for dinner so you have to do ________,” but I also like to feel like someone values me enough to pick up the tab once in a while. We don’t have an actual system like some of these comments suggest, we just figure it out as we go along.

      Granted, that is what works for me, not necessarily you. But if you’re feeling uncomfortable, I agree with all these other lovely Homies who suggest talking it out with him. I’ve been on plenty of dates where I just outright refused to be paid for, mostly due to reasons similar to yours (especially the feminist beliefs and being used to being single). But there’s always a third option that can work for both of you, and you can only reach it through communication 🙂

    • Oh, I know he’s not wrong and I honestly think he does it from a place of chivalry which is very sweet. I think finding the right arrangement that works for everyone and makes everyone feel comfortable can take a bit of work, but it sounds like you have one that works for you guys!

  11. “I’ve spent most of my adult life paying my own way and it’s hard to suddenly accept that someone now wants to do it for me and on a regular basis.”

    It is hard to go from being independent to having someone want to pay for you, as well as going from “friends with benefits” to a romantic relationship. Both feel strange and complicated, but you’ve got some great suggestions above.

    When my husband and I were dating (didn’t go from ‘friends with benefits’), he made more than I did. Early on we’d go dutch. But as we got more serious, he’d go to pay for things, and I’d more often than not offer to pitch in, whether that meant splitting things 50/50 or tossing in $20 or whatever. Sometimes I would split or contribute, sometimes he preferred to treat. But we talked about it each time, and it all balanced out. (And to be honest, sometimes it was nice to be treated, as weird as that felt at times *smile*)

  12. I think early on it’s okay to shut up and let him pay. But after a while guys like to know that they’re not EXPECTED to pay every time. First and formost you should communicate how you feel and find out how he feels. Maybe start off by saying “I don’t want you to feel like you’re expected to pick up the check every time we go out.” To follow up you could invite him out and treat him. If he is buying you random gifts (Mmm cupcakes…) maybe you could get him random gifts too.

  13. Yes, duh. Nothing says you can’t buy surprises and shit for him, too, whenever you want to. Enjoy being respected, fer chrissakes.

    • But why is it respectful to be paid for? I don’t mean to be snarky but seriously, why is that someone voluntarily spending time with another person , sharing their body with them etc is not already a clear cut sign of respect, why does it need this financial confirmation? I’m really asking this to people in general more than directly at you Jane, hope that’s clear.

      Consequently if I go out with someone and I haven’t already talked about paying and they don’t offer does this mean they don’t respect me? Should I consider that I’ve done something wrong if I don’t get the “respect” at the end of the date? And what should I do in return for the “respect”? What kind of girls get “respect”?

      What I’m getting at here is the underlying issue with being paid for on a date as reward or more worryingly, confirmation of worthiness and the implication that one’s own validation of worthiness needs confirmation and is not sufficient on it’s own.

      In non-romantic contexts one person paying for the meal (or other stuff come to that..) is equally fraught, think about businessmen competing to pay for lunch, it’s clear that whoever gets to do it has one over on the other. It can be awkward between friends when one of you tries to pay for everything, in my experience it takes being very well established friends to be able to do this. I’m not talking about things like the common practice of a small group of friends alternating buying drinks for each other in rounds over an evening, I mean more that thing were two couples go out and one couple tries to pick up the whole tab unwittingly humiliating the other.

      I’m not saying one person or party paying is universally wrong but it does create an imbalance and this usually requires a pre-established relationship where you can take turns and even it out. When you are just starting dating someone you don’t yet know if this is going to last long enough to be something where you get to take turns, which is why in my book it’s good to be clear from the start.

      • I get what you’re asking, and why you’re asking it. I think it’s a complex thing that depends mostly on the individual circumstances.

        My current husband and I have pretty blended finances, and that is fine. We run a business together, so it was more convenient to just sort of put everything together. Therefore, it does not matter really who pays for what…because it is all coming out of the same pool. It took a little getting used to, but it works and I don’t have any icky feelings about it.

        Before, when I was young and dating, I was 100% pay my own way on dates, especially “casual” dates. I’d had it drilled into my head that men paying for dates equals expecting “something” in return, so I always carried enough cash to pay my own way even when I was broke as a joke. But when I got serious with my now ex-husband, we went Dutch. Always. Down to the last penny. And at first this was fine, because like I said, I liked to pay my own way. But once the relationship got serious…it was different somehow. I can’t even describe it. Even after we lived together, even after we were MARRIED, he insisted on splitting everything. Like, we’d go to the grocery store and get separate carts and he’d pay for “his” groceries and I’d pay for “mine.” We’d split the dinner check, split the utilities exactly by half in our shared space, if we went on vacation, we’d split the cost of hotel down the middle. After awhile, especially since he made 3x what I did, it got to be something that made me feel bad. I no longer felt like an independent feminist who was paying her own way. I felt like I was married to someone who thought I wasn’t “worth” a goddamn dinner at Applebees on him every once in a while. I kept telling myself it was stupid, because hello feminism…but when your husband wants to go out to eat somewhere nice, and he can afford the whole check but you have to give him your share out of your decidedly less income, it gets pretty annoying and disrespectful feeling after awhile.

        So, yeah…happy medium, I guess. There has to be one, and both parties have to be in agreement about it, or it WILL become an issue down the road.

        • This reminds me of one part of The Joy Luck Club… pretty much exactly. They would split everything… He would even tell her that her birth control was her expense not his. And that he shouldn’t be responsible for paying for the ice cream because she bought it. That sounds like a horrible way to be married.

          My husband and I still have separate accounts (though we bank at the same bank and can see the balances in each account), but we have a joint credit card that we put most of our purchases on. I pay the credit card bill which means groceries, house stuff (toilet paper, shampoo, etc), going out to eat, as well as bills that can be paid to credit card like my cell phone, the cable, etc. He pays all the other bills (including the mortgage).

          When we were dating, he paid for everything for probably the first month or so, but then we would split things. Not usually do split checks at the restaurant, but if we did dinner & a movie, I’d get the movie tickets and he’d get the dinner, or he’d get drinks, and I’d pay for bowling, things like that. It didn’t always work out to an “even” amount, but I don’t think either of us was “keeping score”. I also sometimes would treat him because I wanted to. He never made me feel obligated in any way because he paid for things, and I certainly hope I don’t make him feel that way.

  14. Yeah, my guy and I go back and forth. I pay for dinner one night, he pays the next time we go out. I like that because we each get the chance to treat each other.

    If we’re doing something really big–a trip or a concert–the person whose idea it was generally takes the bulk of the cost and the other person will pay for snacks, gas, whatever. As you get deeper and more serious in a relationship, obviously there are going to be financial issues that come up more often: “Hey, I’ve got that big insurance payment this month, can you pay for all our dates and I’ll get you back later?”

    Everyone just has to figure out what’s right for them. I also wouldn’t be comfortable with my guy paying for everything, even if I knew he could afford it, because of equality and all that good stuff.
    All that said

  15. I think this is less about whether he’s happy to pay, and more about the fact that you’re NOT happy NOT paying (at least some of the time). And I think that’s how you should approach it with him. Tell him how you feel, but frame it as “I really want to do these nice things for you, too,” instead of “I feel bad that you pay for everything.” Relationships have a lot of give and take, and right now he’s doing all the giving, at least in a monetary sense. You need the opportunity to do that, too, or you’re going to feel like a pet instead of a girlfriend.

    • I agree about shifting the perspective of the conversation.
      Nothing spoils a coffee date for me more than an argument over who’s going to pay. If one person offers, let them pay. Then you can offer to get it next time. Fighting over less than $10 is stupid in my opinion.

  16. Can I just say, CONGRATS on finding someone that you had sexual chemistry with and had that lovely discovery that you have emotional chemistry too! As if dating wasn’t hard enough.

    Buying the meal for a date is a gift, like flowers, but better because it’s fun times out and experience with your main squeeze. Try to see it that way, he’s buying you a gift, and maybe it’ll feel better. ALSO! Buy him the gift in return! I love saying, “I got this one,” after a wonderful date. He’ll say, “No, honey, it’s ok,” or “Are you sure?” and I’ll say, “Yes, I want to,” and we’ll both be happy. Maybe you’ll feel better about him paying if you pay what feels like an equal amount of the time.

    Then, of course, get to the make-outs.

    • The really good sex has actually gotten WAY better since we started dating and I think the emotional chemistry has something to do with that!

  17. My bf makes 3x more than me, and enjoys eating out more than me, so I let him pay for dinner. Once in a while, if it’s a smaller bill, I’ll pay, but overall, he pays. I pay for movies and concert tickets though, because they’re important to me. I also will buy groceries and cook more, because I feel better about myself when I eat a healthy real food meal, than bar food (his choice).
    I’m not a huge fan of him paying for me, but I like that we split costs based on what’s important to us, so I’m not resentful of being forced to pay for something that I don’t want to do (eating out for the 3rd time this week, ugh).
    We didn’t really talk about it though. I just started buying tickets (all beforehand, my movie theater has an app, so he didn’t realize I paid until after we got in, and now it works for us) and pointing out that he paid for dinner. And I like to coupon, so I was paying for groceries anyways.

  18. When I first started dating my now husband we had an unwritten rule that if you suggested the date then you paid for it. It worked really well because it meant that when one of us was a little tight for cash they suggested doing things that were cheap or free, but when we were feeling flush we suggested doing things that cost a little more. It also meant that we never had that awkward situation that you go to a really fancy restaurant and only order salad because it’s the only thing you can afford.

  19. I feel like you’re not really upfront and into this guy (besides the sex).

    Most of my relationships started off with casual sex that led to long term relationships. I’ve been the same throughout keeping my independence with finances.

    Just be upfront and say your not used to having your meals paid for. Offer that you’ll take/plan a date that you’ll pay for. Or do the obvious and split down the middle.

    If he can’t handle the spilt bill or you paying for some meals, you probably won’t be lasting long with him anyways.

  20. My husband and I are in the same income bracket, so we split everything 50/50. Sometimes I treat him, and vice versa. No conversation needed. Men are no longer the primary breadwinners nor widely expected to pick up all the checks, and we can do more fun things together if we both use our incomes.

  21. I would suggest that if you are hoping for this relationship to continue into something with potential permanence, staying quiet about things that bother you and make you uncomfortable is not a good strategy.

    Relationships need to be able to withstand a few tough conversations because as life goes on, the tough conversations are inevitable. And money conversations are hard in general. Seeing how you each react to having this discussion will help you figure out if this is the right relationship for you.

    That being said, it doesn’t have to start out as a tough conversation. You could just casually mention at the end of a date when you thank him for paying that next time you want to treat him, maybe even suggest where and when next time could be. If he accepts it easily then the transition may not be that hard to make.

  22. When I was in college, my boyfriend had more money than I did and consequently he paid for more things than I did. But since then I’ve always shared the cost with whomever I’m dating. Not in a ‘split the bill’ kind of a way but more of a ‘you paid last time so I’ll pay this time’ approach. I think I would feel uncomfortable otherwise.

  23. I typically alternate on paying for things, but I also like being paid for from time to time. I’ve also dated someone that made a lot more than I did…and so I had no problem letting him pick up the cheque at certain restaurants while being the one to cover cheaper dates. I made peace with it.

  24. I think every couple needs to strike their own balance. And BALANCE is the perfect word I think.

    You don’t need to be like other couples. You don’t need to give up your offbeat-ness. But you don’t have to be not like other couples – or uncomfortable either…just talk with him about it and strike a good balance that works for the two of you…

    Best Wishes for you!!

  25. Thank you SO much for all of your comments! I want to make it known, though, that in the original letter I sent it I made it clear that I do sometimes pick up the tab or do the surprises or whatever like he does. He still pays about 2/3s of the time — but reading this with that omission gives it a totally different tone than what my original letter had.

    • WHOA! You’re right! That section totally got deleted, and I don’t know why! Seriously, I edited this myself and there’s no reason why I would have cut that. Definitely got cut my mistake. I added it back. WTF, Megan.

    • With the new information in mind, I want to amend my earlier advice since it changes the dynamic. Still talk, but I’d recommend looking for a good solution for the two of so that you don’t feel like he’s dominating the paying aspect of the dates.

      It sounds like you have a great amount of emotional closeness, which should help the discussion along a bit (knowing more about how you talk and any quirks in how you speak when you may be emotional/stressed about something).

      I’d still recommend a neutral-ground time and place for the discussion given that this is a sensitive topic for you and may be a chilvaric position for him (in the classic sense, not in the strictly-sexist way).

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