I have a good friend and every time we go out for a drink or dinner, he always insists on paying. That sounds good to have someone pay for you but it's actually not. For a start, it's kind of condescending.

He is very successful and has a lot of money and I have a feeling that he does it because he feels like it would be an insignificant expense for him and a costly one for me.

I know he does it with other friends as well so I'm sure it's not personal. However, it isn't something I feel comfortable with. It comes across a bit like he's showing off and trying to shift the power dynamic.

There's also the annoying ritual at the end of the meal where we fight for the check. This is probably the worst part. It's probably quite comical to others seeing two grown men almost come to blows over trying to pay.

I've spoken to him about this. One time, I told him I would definitely pay for the meal. Halfway through the meal, he said he had a phone call and secretly paid for the meal.

At this point, I have to say he is a good friend in every regard except for this. I would like to keep the friendship. Basically, he is very insistent on paying and treats it almost like a game whereas I really just want to pay for my share.

My preferable option would be to just split the bill each time or have an informal arrangement where I pay sometimes, he pays the other times.

I mean, if he really does insist on paying, I guess I can probably live with that. I just don't know how to do it without it being awkward.

I REALLY don't want to get into an argument at the end of each meal. However, the objecting to paying is almost a ritual at this point to show that I'm grateful. I think it would be weird and disrespectful if I just assumed he was paying each time without kicking up a fuss.

How should I approach this situation next time I'm with my friend?

My friend and I are both Canadian.

  • Is there a significant difference in age?
    – user4788
    Dec 26, 2017 at 0:46
  • 2
    Maybe this is a cultural thing. I have several Iranian friends and getting in to a physical fight for the bill seems to be standard procedure for all of them.
    – Orbit
    Oct 18, 2021 at 9:04

8 Answers 8


Jimbo, a possible solution depends whether you want to stay within the competition or redefine the rules.

I really doubt that winning over him will work more than once, as you say it is a game, and he likes to play it by his rules. He even tricked you after you explained that it was important to you.

If you consider it a kind of sport and would like to win, you could talk to staff in advance and...

  • pay in advance („I‘ll pick up the change before leaving“),
  • have your credit card pre-charged before you even order
  • arrange to have the bill sent to you by email/mail and pay it afterwards (please consider I live in Europe and don’t know what payment options are possible in Canada).

As an upside, you would probably take him by surprise and be able to enjoy his facial expression at the end of the meal, at least once.

To play hard would be to refuse going to restaurants with him if he refuses to respect your desire, but is this worth it?

Here’s another thought:

I mean, if he really does insist on paying, I guess I can probably live with that. I just don't know how to do it without it being awkward.

This opens the door to another game.

One of my mentors used to share the secret of happiness with me:

Take what you get when you get it, and don’t take what you didn’t get when you didn’t get it.

You could practice to take what you get, and learn to let go of having to give back.

Obviously your friend doesn’t expect anything in return, and it might be his way to justify his wealth by being generous and sharing it.

A simple

Thank you, I really enjoy our time together, as well as your generosity.

might be more than enough.

You could try it.

I’ll predict from reading your post that probably part of yourself will criticize the rest of yourself.

You might want to listen carefully to this criticism and even write it down for yourself. Why?

These thoughts are often automated thoughts that cross our minds involuntarily and quickly. By carefully observing and writing them down, you’d give yourself a chance to actually question and check the truth and the usefulness of these thoughts.

If they are neither true nor useful, do not act upon them. This will feel strange in the beginning, but will improve with training.

If you want to pay for your meal nonetheless, you could do so by letting him pay and donating the money you wanted to spend to someone who has less and then can have a meal, too.

This way, you would expand the game and let others enjoy it, too.

  • As a non-native speaker I did not understand the "don’t take what you didn’t get when you didn’t get it." part. Care to elaborate? Jul 16, 2018 at 12:31
  • 1
    @ThorbjørnRavnAndersen It essentially means that "if you weren't given something, don't try to take it anyway", with the implication that trying to take something that wasn't given to you in the first place will bring you trouble
    – user18495
    Oct 5, 2018 at 18:10

Try investigating the reasons why he pays for you every time. If his answer will be just "because I can afford it", push the enquiry a bit further until his feelings about the topic show out. Probably the final answer will be something along the lines of "because it makes me feel good, it's a pleasure to pay for a friend". Your reply can be:

I'd like to have the pleasure of generosity as well from time to time. Let me pay this time, let's share the pleasure!

This way, you'll reframe the problem as a matter of feelings and not only of money.


This is what I would do. A real human with social skills may well do something different :-)

You have made it clear in the past that your friend's behaviour is something you're not comfortable with so it appears they are ignoring your wishes. You then just have to decide the following:

Which is more important, your wishes or your friendship?

If the latter, suck it up and let them pay. I'd make it clear that you would prefer a more equitable arrangement but that you're tired of arguing about it. Maybe at some point they'll realise how much money it's costing and back off (you could record every meal and just deliver the running tally at the start of the next one, that may get their attention after a few dozen meals).

If the former, make it very clear one last time that this makes you uncomfortable and that a friend would not be putting you in this position.

Then deliver an ultimatum (tactfully, of course): either they allows you to pay your fair share of the costs, or you stop having meals with them.

To be honest (and this may well be contentious), this seems to me little different to a man continuously "hitting on" a woman who just wants to be friends, and has made that clear. A smart woman wouldn't stand for that, nor should you (male or female) stand for someone disregarding your clearly expressed wishes.


Here in Quebec you can ask for two separate bills and it is socially acceptable.

However, whenever I visit friends in Toronto it seems to be customary to have one bill between friends and one person takes care of it. In that case, you can always try this method, but this may be a faux pas in your area. If this is the case, when you are ready to pay and you see the waitress, tell her you will take the bill and be firm on this. Your friend may say that he will take the bill, just tell your friend "I insist." and look at the waitress and say "I'll take the bill. Thank you." without giving your friend a chance to respond to her. When she arrives with the bill, she should hand it to you.


If this friend will not let up about paying for the check, offer to cover the tip. Make sure you have cash on you whenever you go out to eat with him and when he insists on the check, say you'll cover the tip, take your cash out, and set it on the table.

You could make it a point that if he wants to continue picking up the tab, you'll make sure to cover the tip each time, hopefully alleviating that awkward check dance at the end of the meal.

I believe this is a good way to allow both parties to "get what they want." Your friend clearly likes to pay for the meal for whatever reason and you want to feel like you're contributing so let him pick up the tab but cover the tip so you contribute to the overall bill.

  • 2
    Hey! Can you please edit this answer to explain why you think that this a good thing to do - like, how exactly does this solve the OPs problem? What effect will this have? Why does this have that effect?
    – Mithical
    Dec 28, 2017 at 23:07
  • If the friend has 10 times more income than OP, then the friend paying 10 times more than say a 10% tip seems quite reasonable.
    – gnasher729
    Oct 17, 2021 at 21:31

As you have mentioned that your friend pays every time you go out together and it has become annoying for you, I get the feel that he is a very good and close friend of yours. While it is normal for close friends to insist on paying the bill, I think this has gone one step too far. Perhaps, your friend wants to save you the cost of a restaurant meal which he can easily afford and thus chooses to do so.

If you feel annoyed and perhaps insulted by this attitude of his, then, I think the best option is to tell him in clear words, "pal, I appreciate the fact that you are willing to pay for our meal but this has gone for way too long and by now, I am annoyed and in fact insulted by this. Please refrain from doing so in the future." Or something along those lines. Doing this will probably help him realize he is not doing you some favour by paying the bills. Rather his actions have caused you much annoyance. If he is a good friend, obviously he would try to make you feel better and maybe allow you to pay the bill sometime.

If that doesn't work, the second best option according to me is to say that you won't go out with him anymore if he continues to pay the bill every time. He definitely wouldn't want to lose a close friend too and perhaps might soften his stand.

  • 1
    While I disagree with the downvote, the answer is missing a different point of view. The OP would need to explain why he would no longer be going out to dinner, and give the friend a chance to change. Saying "because you pay the bill everytime" isnt a good reason because it doesn't address the OPs original comment. It might also leave the friend confused and they might not see anything wrong with paying the bill each time. So why would that be something the OP is upset about? Your answer needs a little more clarity
    – Chillin'
    Mar 1, 2018 at 10:36

I mean, if he really does insist on paying, I guess I can probably live with that. I just don't know how to do it without it being awkward.

You friend wants to pay and you don't really care, so just let it go polity. When the bill arrives, say: I think it is my turn. If you get turned down respond: should we just split it. If that is turned down, just say thanks, I will get it next time. If the bill never arrives, just say you seem to always win this game, are you sure I cannot pay (likely followed by thanks, but let me get it next time).

If you don't play, your friend will either stop, or feel good about themselves. Either way it is no skin off your back.


I'm one of those guys.

While I'm trying to save for a big investment (so what I do is actually a sacrifice), I feel I'm blessed with greater success than some of my friends', therefore I genuinely feel to share a part of it with them. I try not to show off, but sometimes I realize this can be the feelings of those who accept a meal or something to drink.
It has happened to me to fight over a bill, and let me tell you once again, it was not about showing off, but rather about being generous.

So unless you have a serious reason (e.g.: him boasting about his job and/or bottomless wallet) to think that he is showing off, I'd suggest a "return-the-favour" policy, which is what I have with my friends:

Basically, if they get annoyed by me paying the bill and especially if they offer me money (which I won't accept), I say that I'm accepting liquid refunds only, and that's final. Provided it doesn't need to be the full amount of what I paid, they can offer me a beer, a coffee, a cocktail, whatsoever. In this way I'm allowing my friends to repay me up to a certain extent and I spend more time with them (which, at the end of the day, is the thing I enjoy).

Could you propose/accept a similar policy and allow your friend to "show off"?

  • 3
    'It has happened to me to fight over a bill, and let me tell you once again, it was not about showing off, but rather about being generous.' But why cant you allow other to share in that feeling? Why does your need to be generous trump theirs?
    – user9837
    Jan 19, 2018 at 17:10
  • It doesn't. Your question is misdirected. I already explained the motive already Jan 21, 2018 at 20:06
  • 2
    yes you explained your motive, I asked why your motivation to show generosity trumped the desire of your friends to do the same.
    – user9837
    Jan 22, 2018 at 7:33
  • 3
    You've lost me. All I want is to understand why you would rather argue with your friends than accept that they may also feel blessed (if to a lesser extent by your standards) and wish to share that with you. If you feel it is justifiable to insist, could you tel me why it is.
    – user9837
    Jan 22, 2018 at 15:49
  • 1
    I don't understand as well, it's not because you win more than another that he cannot pay his part. If you do that occasionally, why not. But if you do that every time, I would personally take offence and think of you as boasting. You can be generous by so many other ways as a friend than with money.
    – Fanie Void
    Nov 19, 2020 at 10:37

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