Paying for It

In which some of the mysterious social aspects of money and its exchange are respected.

That clatter of china and glass and silver, the chatter of a hundred conversations, none of which you have to follow, light bouncing off walls and faces and brass things and glass things and wood things and bottles of wonderfully poisonous things. Stunning hosts, waiters in black and white with clean faces and neat hair. Dark spots where snuggling is overlooked, bright spots where cynicism is almost appropriate. Big loud places, small loud places, the elusive quiet cafe that is still warm and alive. I love restaurants.

And yet there I am, as seldom as I can arrange, surrounded by this sure magic, choosing not to eat. Does this happen to you?

It’s about money much of the time. Worse than sex it sometimes seems. I would feel more comfortable even now discussing the details of safe dallying or the effect of controlled breathing on orgasm than the ins and outs of money between lovers and family and friends. And the very people who are looking at this page saying to themselves, “What is with this girl? Why is she so wound up about money? Clearly she has a bit of a problem and should resolve it rather than projecting onto the rest of the world,” are the very people who offend others so deeply on one occasion or over the course of many that they end up with friends who will not go out to eat with them, and if forced to, won’t order anything, will pick at what they did order, go home and eat leftover tikka masala from the night before when they shared one of those warm bright, careless and safe evenings with others. Perhaps even in the same restaurant.

The trickiest thing. Or not tricky at all. Or extraordinarily tricky for one person and just another meal to the other. And you have no way of knowing if your companion is in the former category if you are genuinely in the latter. Some people simply refuse to eat with more than three other people at any one time, and then only with those people who they know to have compatible attitudes about money and restaurants. Or they dine out only in such situations as they will be able to simply pick up the check themselves and be done with it. Others go about their lives and never notice that some people dread eating with them and avoid finding themselves at a restaurant table with them except in the narrowest of circumstances.

Yes, well, what do I have to say about all this? Not much. I have seen friendships wither over stinginess. Other entanglements dismissed for the opposite reason. Too generous. Frantically so.

No matter what approach to money and the sharing of food one chooses or finds oneself inconveniently possessed of, it should be acknowledged that others notice and are affected. One way or another. Good, bad or indifferent. Sometimes it will match, sometimes it will be in opposition. In any situation, seek resolution that maintains dignity and good humor. It can require a sort of social and economic self-defense.

Are there any rules of thumb? Unfortunately not. The rules of behavior that one group considers written in stone comprise for others heinous and unforgivable comportment. The only safe way out of this dungeon of discrepancy between what might otherwise be very close friends is often very taxing on both your pocketbook and your stores of goodwill. It might involve picking up the check discreetly, demurely and often. It might also include on many occasions a bit of improvisational skill as you explain why you are picking up the check. It won’t do in most cases to say frankly you do not care to undergo the humiliating process of dividing up the check,1 that you simply cannot bear the idea of listening to people you otherwise love try to claim they only drank a half a glass of wine, that their salad was a dollar less than someone else’s, and who even cares because they never add a reasonable tip nor the appropriate tax to what they think is their share. You end up paying twice what you would have if you had come to the restaurant on your own, you begin to wish you had, and your evening is severely soured by listening to this gibberish.

Another equally miserable resolution, endured most often by women but any light eater is a potential victim, is to good-naturedly agree to split a check equally when one has barely eaten at all, has shared a pasta with another at the table while some of the other diners had grilled sea bass, salad and dessert. Unwilling to ruin the rhythm of the evening by discussing the check, the light eater is in terrible danger of feeling abused and resentful of their brutish and gluttonous companions. What’s worse, there are those who consider this a reasonable way to behave at a table of dutch diners. They will even tell you that when the check is to be split equally, they just order whatever they want, and aim for the most expensive stuff at that. You look at them and wonder if you should tell them they can lose friends that way. People are quirky about money. People notice what you do. The only time they don’t notice is when they come out ahead. Then they are mercifully blind to what has transpired.

I swear money is more difficult than sex, although the routes through the various impasses are strangely similar. Unstated generosity to the degree you are willing and able, and then the graceful but complete extraction of your own self from abusive situations when you are no longer willing or no longer able. At some point, in either realm, it might be right to let your companion or companions know you are having trouble with a particular thing, are trying to resolve it, but that if they keep up the same behavior it is possible you will simply slip from view. No threats, no ultimatums. Just honesty, honestly owning your own frailties that contribute to the problem. They in turn can choose to modify their approach to whatever it is, or they can choose not to. Later, when you call up to say hello from your new home in the outskirts of Barcelona, they won’t be able to accuse you of having been uncommunicative, of not having warned them, of neglecting to give them an opportunity to make the small or gigantic alteration in their make-up. It is some solace.

Back at the restaurant, it is best in many cases, and if at all possible given your finances, to come up with some plausible reason for buying the others dinner. Don’t do this all the time, mind you. You do not want to go broke, nor lose all affection for your penurious friends, nor make them feel you have some odd agenda.2 Another often successful strategy is to be assertive and fair in splitting checks.

As it turns out, people end up eating out with others who match them philosophically at the table.

Light eaters congregate, allowing only the extremely polite glutton to join them more than once. They will be most elusive in their movement from place to place, knowing nobody is loathe to dine with them. They split the check amongst themselves, sensitive to small discrepancies. They err on the side of generosity. And why not? The check is always pathetically small. A wild boor could easily join them, order a fabulous meal, split the check with them, utterly blind to the structure of the group, and find they have eaten extremely well for extremely little. For this reason, light eaters leave for dinner early and without announcement, or after everyone else is gone.

People who like discussing the bill and deciding who owes what down to the dime, those people who carry little plastic cards for figuring out the tip exactly; they, too, end up dining together. It is difficult for people not raised with such habits to stand them. It seems ridiculous to them not to figure out the check to the minute, and it is ridiculous to everyone else to be so fanatical about a matter of cents. Especially when it is the waiter who most often suffers. However, if one is going to be a fish out of water, this group is not so bad. You will only end up paying a bit more than your share to make up for the small tip. A little meditation while they figure out the details of the check, or a trip to the restroom can alleviate the small discomfort of watching people you otherwise admire become briefly monstrous.

Meanwhile, people who are careless about money, who eat all they want and then are happy to split the check, knowing they ate as much as anyone and that they will not be caught with the short end of the deal, they also end up eating together. This is generally because no one else wants to eat with them. No one else can afford it. No one else wants to spend so much money on food they don’t eat without the pleasure of actually offering a gift to another. This group is usually quite open with invitations to join them, although they are as unwilling as the first group to include a second time someone who has shown themselves reluctant to play by their rules.

The worst possible position in terms of courtship is to be dining with people who contribute to a check in a miserly fashion, forcing you to make up for their close-fistedness surreptitiously or suffer a scene of money changing. Rather than having made others feel taken care of and honored, rather than feeling good about having given a small gift to others for no reason, rather than having avoided the check squabble entirely and all that that implies for the magic of the evening, you are instead in great danger of feeling resentful. Poison to all courtship, and the antidote is capricious and rare. I’ve never seen it myself. If the culprits persist in their penny-wise ways, or allow you to pick up the check more than twice before saying Oh no, it is my turn, you have several options and none of them are great:3


Stop discussing the check entirely and let the others figure it out. Pay what they think is your share, and then discreetly leave extra to make up for the invariably meager tip. It is most important that the waiter think highly of you. Otherwise you might get hideous service at a later date when you are with less scurvy friends or colleagues.


Grab the check and say, “I used to wait tables. Let me figure this out,” and then do, including a generous tip. Inform each person of exactly what they owe, rounded up to the nearest dollar. One method is to divide the check equally and then add a couple dollars or subtract according to each person’s meal. A girlfriend who was a waitress in Manhattan and is good at this sort of thing recommends this, but adds that you have to do it in a very forceful and authoritative manner. If anyone criticizes your math or claims they owe less, you can chastise them good humoredly about being cheap.4 The rest of the table should rush to your side in support since to reduce that person’s share by even a dollar would increase their own share, and they surely won’t want that.


Stop eating with those people. If you are forced into going to a restaurant with them, and you know you will be made unhappy by the resolution of the meal, refuse to eat for one reason or another. You already ate. You have a date later where you will be expected to eat. You aren’t feeling well. Or get whatever you want, but come up with a reason to leave before the rest of them are done, paying for your own meal and tip on your way out. Don’t ask for separate checks. It makes the waiters nuts and they still don’t get a good tip.5


Unless you are tormented by such colleagues on the road, you can step lightly around the whole thing by suggesting dinner at your house instead and then tell everyone what to bring. Don’t wait for them to ask. “You bring two bottles of wine.” “You bring a green salad.” “You bring dessert.” Contribute something yourself. The end. Or offer the meal to them as a gift and forget about it. It will not be returned. Don’t ever mention why you do this. Only agree to go to a restaurant with these monkeys when you feel as though you can withstand the assault on your good graces and your bank account, cheerfully and without remark. Ever. You’re an adult. Do what you want to do and don’t do what you can’t do happily.


If it is just a single person who drives you nuts, try to invoke a pattern of alternating who picks up the check, trying as well to be the person who gets the check on the more extravagant occasions so they do not feel, as they are apt to do, that they are getting a raw deal. One day, pick up the check and announce. “I’ve given up arithmetic for good. Let me get this. You get it next time.” On the next occasion as you enter the restaurant announce, “Oh boy, you’re paying this time. I think I’ll have the escargot and chocolate soufflĂ© for dessert!” Wait until they turn white, laugh, and then order your usual sandwich on rye, no pickle.

Enough already with how to negotiate the herds of wild boars roaming the planet. There are plenty of people who are aware and flexible and generous and fair, and as willing and able as you are to pick up the check with a brilliantly fabricated excuse or honest expression of spontaneous generosity if need be. Plenty of people accept a broad spectrum of possible attitudes and behaviors without judgment. Find them and hang around with them.

Those you eat with are those you are closest to. Best to be forgiving and come up with solutions which entertain you rather than throwing out perfectly good people just because their parents missed a couple beats.

paying for all of it

There are also plenty of people whom you really and truly do want to take to dinner, who are precious and delightful and who will fight you for the check. Or people whom you must take to dinner for one reason or another. Whatever the case may be. Buying someone or a bunch of someones a meal can be a lovely thing to do, but just as a resentfully prepared meal can be worse than no meal at all, you can easily pay a check in a way that makes others wish you hadn’t. Think of all the ways others have made you uncomfortable and don’t do any of those things.

Now, how to go about paying for a check so that the gift you are giving is received in that glow of good humor so conducive to any kind of courtship, be it professional, political or personal.6 Before we start, let me remind you that your underlying motives for picking up the check must be genuine and irreproachable, or you will have to be a better performer than I am. If you are acting from a point of sincere generosity, either from spontaneous or premeditated good-will, you are on your way to doing it well. There are still a number of traps. Everyone’s parents should have taught them these skills, but unfortunately everyone’s parents do not possess them themselves. Fortunately, they are not so difficult to pick up.

At some point the check comes. Do what you want to do, naturally. But if you want to feed someone, try some of the following approaches:

Invite another to dinner. “I want to take you out to dinner tonight,” you say to them. “Humor me,” you can add, if they look at you sideways. Unambiguous, and the evening should go just fine as long as you behave magnanimously and not tyrannically. Do not undertip nor be precise about it. Do not be rude to your server. Do not chew with your mouth open nor talk with your mouth full. If there is a problem with the bill, address it discreetly and professionally. Do not embarrass your companion. Do not make a big deal out of buying them dinner. It is not a big deal, unless you do it in such a way that they feel very very cared for and complimented and you do not make a big deal of it. Your gift is for naught if they have even the barest suspicion of owing you something. They should feel instead that they have done you a great honor by allowing you to take them to dinner. That they have made you extremely happy by agreeing to spend the evening with you. Of course, that should actually and obviously be the case and you shouldn’t have to make any effort to convince them of it.7

In the event that there is no reason for you to be taking them to dinner, and you fear they might hesitate to agree to such a thing, you can deploy one of a number of techniques improvisationally at the restaurant.

One possibility is to get it over quickly with the very casual comment as you open the door to the restaurant for them: “By the way, my treat.” Or later on, if it is just the two of you, be the one who asks for the check. Do not do it so early so your companion thinks you are trying to cut the evening short. If they appear to be trying to capture the waiter’s attention to get the check, outstrip them. Say something like, “Are you ready to go? I’ll get the check.” When the waiter appears, and without being silly, ask for the check yourself. When the check is placed in front of you, pull it toward yourself possessively or discreetly place it even further out of reach of the other. If the check is not put in front of you, for whatever reason, reach for it immediately and gain possession. Do not let it sit on the table unclaimed. Say in a selfish tone of voice inappropriate in any other situation, “That’s mine.” You don’t have to look at it right away—in fact you probably shouldn’t, thereby making the dramatic point that it doesn’t matter what it is, it is yours. You certainly don’t have to destroy the rhythm of conversation to accomplish this. But you do have to take possession of it immediately. The longer it sits there, the less convincing you will be when you try to claim you really do want to pay for dinner. “Right,” thinks your companion. “Whatever.”

Meanwhile, if you are planning to take someone to dinner but you suspect they are not ordering freely from the menu,8 make it clear it is your treat tonight. Encourage them to order what they want by recommending items on the menu which you have noticed are particularly extravagant. Say, “You should try the abalone! It is delicious here.” Remind them it is your treat and encourage them to take merciless advantage. Few will bleed you at the opportunity, and you will set an excellent tone of generosity regardless.

Another trick is to ask for the check, get it and pay it while your companion is away from the table. When it is time to leave and they ask about the bill, you say, “I already took care of it.” When they protest, smile and tell them it had been your despicable secret plan all along and now they are your plaything, ha ha ha!

Of course, it is possible that someone does not want to be taken to dinner, is unable to accept a gift freely offered and will insist upon paying their share. If they really do insist and it seems there is some quirk behind it,9 let it go. Underestimate slightly what they owe and insist that you are right. That gesture should be a gift which they can accept and which they will silently appreciate. Or suggest you were hoping to linger late in a cafe down the road and that if they will let you buy them dinner you would be honored to accept a drink from them later in the evening.

There are so many lovely ways to be generous. All you have to do is think to yourself, “If I were sitting across from myself, what would make me comfortable?” Say and do whatever would make you think, “This is the sort of person I would like very much to be around.”

And now we come to the most fun part about buying dinner for others. Buying dinner for lots of others. Here’s what you do if you have any reason to think others at the table will try to thwart your generosity: At some point during the meal, surreptitiously let the waiter know the check is to come to you. One good trick is to drop by the wait station on your way to the washroom, give them some plastic money and ask them to write up the whole thing before bringing it to the table. Then if there is any dispute, you can claim possession is nine-tenths of the law.

If a meal is leisurely enough and the waiter is not prompt with the bill, you will have plenty of time to excuse yourself for any of a number of reasons, make your way to the host station where you can wait for the bill to be added up, check it, figure the tip, pay for it and return to the table. When it seems to be time to go, or when someone mentions it is time to get the bill, you reveal that it has been taken care of. Nothing anyone can say will change that, and in the end they will be forced into accepting your gesture. However they may insist and seem to refuse, everyone is always delighted to not have paid for dinner.10 The more nonchalant you are about the whole thing, the more content you seem at having outwitted them in the who’s-going-to-pay-for-dinner competition, the more they believe you are truly happy and that they owe you nothing, the warmer they will be toward you and the world at large.

Of course, if it was always understood that you are to pick up the check, you should do away with all such devices and simply be sure to ask for the check and take possession, underscoring your generous intention with graceful action.


1 Sometimes you can be that frank, though, and to wonderful effect. Very advanced stuff, mind you.

2 Another extremely rare possibility is that you might make others feel as though you don’t think they can pick up the check. This would only come up if you are fabulously rich and already so generous you pick up the check too often. As faults go, that is not so bad and darned forgivable. But be sensitive to the egos of others nonetheless.

3 I am making the broad assumption that you do not want to cut off all contact with these peoples, or cannot for business or family reasons. Also, money is a strange thing and does strange things to most people. Surrender. Unless you are tied closely to someone, money quirks usually can be side-stepped. You shouldn’t dissolve friendships over it unless it seems to speak of other things.

4 Assuming they are not financially strapped so that a dollar does matter. Be flexible and compassionate.

5 “What is with this author and tipping?” you are thinking to yourself. It is the first rule of romantic and probably all other courtship. Never undertip. It exhibits stinginess which is a very undesirable trait in a lover or friend or colleague. And if the other ever worked for tips themselves, which many people, especially women, have done, they may, unbeknownst even to themselves, take it as a personal affront and your chances for a successful courtship are scuttled.

6 And while the professional and the political are certainly interesting arenas for courtship, it is the personal which has the fiercest reputation. It might seem that you are simply sharing an evening together or a lunch or coffee, and it has become normal to simply divide the check and think nothing further. Yet sometimes, I would venture to say often enough, it is the desire of one or the other or both to feed the other. And splitting a check does not translate into each feeding the other. The impression is that each has fed themselves. Love does not work that way, ever. Each must always be willing to give entirely, carry the whole burden in any situation, and sometimes insist on doing so. Proof? No, not really. But it is not enough to claim you would caress your lover. Not enough to insist and insist upon being believed that you love deeply and unto the ends of the universe. Either you do it or you don’t.

7 By the way, all this is true for the oldest lovers as well as for the earliest moments of courtship.

8 Women, who tend to be frugal for a variety of reasons, many of which make me so mad I could spit, do this all the time. Keep an eye out for it whether you are a woman or a man.

9 Honestly, why else would someone refuse such a lovely thing as to be taken to dinner? They couldn’t possibly be worried about your intentions, could they?

10 With the notable exception of some business or political sorts who have very strict and convoluted rules about whom they can accept food from. In the company of such people, it is sometimes entertaining to surreptitiously buy them a meal and then watch them squirm. Mind you, it might be devastating to your greater agenda.

No comments: