I'm not trying to be cheap, but our resources are also finite...

September 11, 2012 6:56 AM

Let's say you have a friend who you can never ditch (think: sibling) who does not contribute to events/outings? What's the best approach to deal with this?

What do I mean by don't contribute?
-If I cook dinner for my husband, me, and sibling, the sibling never offers or shows up with anything to add to the meal. We provide the food, drinks (wine, beer), etc.
-If we have a place to go (drive), sibling never offers to drive. In fact, sibling says that he doesn't want to drive to avoid the wear on his car & spending money on gas.
-If the three of us are out at dinner and forget to ask to have the check split, this sibling never reimburses.

This person doesn't have tons of money, but he does have plenty of disposable income that he uses for video games or other media (tv shows on iTunes, etc). Thankfully, he never asks to borrow cash money from us. And, sibling is older than us (read: not a kid starting out in life, but a grown-up adult).

The real problem here is that my husband thinks we should (1) ignore the issue (we have enough means to cover these imbalances), or (2) joke/tease him into paying his fair share. I feel that (1) is making me want to avoid this sibling and that (2) is passive aggressive and weird. My solution is (3) just tell him that he needs to contribute equally. My husband doesn't like (3) because he thinks it's a confrontation he prefers to avoid.

What did you do in this situation? Are we missing an exciting (4) or (5) that's better than any other solution? Should I just be the bigger person and ignore this sibling's non-contributions? Help us solve this marriage stumper!

posted by Kronur to human relations (38 answers total)

(4) Don't invite this person anymore.
posted by matildaben at 7:00 AM on September 11, 2012 [11 favorites]

you can probably have the relationship or the money, but probably not both. You might want to determine which is more important to you. Once you decide, let the other go and enjoy your choice.
posted by HuronBob at 7:01 AM on September 11, 2012 [2 favorites]

Did you talk to him? You don't need a confrontation, just talk.
posted by devnull at 7:03 AM on September 11, 2012

I'd use your direct approach, but not in a "Come to Jesus" talk, just in each instance when he needs to be contributing.

"We'd love to have you over for dinner. I need you to bring a bottle of wine/dessert/beer/appetizers."

"Yes, we'd love to go with you apple picking! It's your turn to drive, so we'll meet you at your place/you can pick us up at 2pm."

"Your share of the bill is $X."

Each of these would be said with a friendly smile and no further explanations. If he balks, just keep repeating the same thing, with no further explanations or invitations for excuses (e.g., "Oh, well, I didn't bring my wallet." "Well, your share of the bill is $X.")

It sounds like you're magically expecting him to change. You need, instead, to make your expectations clear and make it clear that he's required to live up to them. (Which means that step two is, if he fails to bring wine/beer/dessert, you stop inviting him for dinner; if he invites himself, tell him it won't be possible.)
posted by jaguar at 7:04 AM on September 11, 2012 [59 favorites]

My solution is (3) just tell him that he needs to contribute equally. My husband doesn't like (3) because he thinks it's a confrontation he prefers to avoid.

Honest communication /= confrontation. It's communication! Honest communication up front prevents confrontation later.

When you invite your sibling to dinner, say "pick up a 6-pack and a bottle of wine."
When you have a place to go, say "we'll take my car but I need $20 for gas."
When you go out to dinner, say "we got the check last time, tonight's your turn."

If he balks, then you drink water with dinner, or you travel to the place in separate cars, or you don't go out to dinner.
posted by headnsouth at 7:04 AM on September 11, 2012 [7 favorites]

...the sibling never offers or shows up with anything to add to the meal.

"Hey, we still on for dinner tonight? Great. Can you please pick up a six-pack?"

If we have a place to go (drive), sibling never offers to drive.

"Hey, we still on for the mall? Great. Can you give us a lift?"

If the three of us are out at dinner and forget to ask to have the check split, this sibling never reimburses.

"What would you like?" "The... oh, wait, can we please get separate bills? Thanks."

None of this of course guarantees that he will do any of it, but it sounds like not explicitly asking guarantees he won't. Asking him to "contribute equally" doesn't really work because this is all social nicety and not commune living.
posted by griphus at 7:05 AM on September 11, 2012 [1 favorite]

This is totally the sort of person where, if you ask, "can you bring a bottle of wine or a dessert from the pastry shop?" will just point blank say, "no," and give some lame excuse for why he can't.

I realize you can't "ditch" the person because he's family but... is there any reason you have to be inviting him over, going out to dinner with him, and driving him around regularly? I suspect that if you didn't invite him out, he wouldn't invite you out, and everyone would be happy.
posted by deanc at 7:05 AM on September 11, 2012 [2 favorites]

Instead of having a big talk, can't you just mention it at the time? Normally, I wouldn't offer to host someone for dinner and ask them to bring something in the same breath, but with a sibling, I think the rules are different. Just say, "Hey, do you want to come over for dinner on Sunday? Great, could you pick up some wine/bring dessert/make your famous bread?"

And even if they don't split the check, just say "Your share comes to $X." Even if you're both paying with a card, most places can split the bill onto multiple cards.
posted by amarynth at 7:07 AM on September 11, 2012

I was going to suggest specific ways to force/remind him to contribute, but the car thing is so egregiously self-centered that he has apparently decided that the sum total of his contribution to your get-togethers should be his presence. Either he resents the amount of money that you and your husband make, or he really doesn't want to hang out with you anyway.

So go with matildaben's (4) -- stop inviting him to things.
posted by Etrigan at 7:08 AM on September 11, 2012 [1 favorite]

You guys need to be way better at setting expectations.

"Hey, sibling, what can you bring to our potluck? We're all pitching in and we sure could use a great side dish!"

"Hey, sibling, can we go in your car? I know you are worried about wear and tear on your car, but we drove last time."

As for the check splitting, take cash from him at the table. Split it up right then and there. Or don't forget to ask for a split going forward.

It's not wrong to ask for fairness.
posted by inturnaround at 7:09 AM on September 11, 2012

Oh, and when you're splitting the bill, split it three ways instead of two. That way, what he'll be looking at is two people each overtly paying their share and it'll be a lot more awkward for him to ask one specific person (rather than you two as a couple) to cover his share.
posted by griphus at 7:10 AM on September 11, 2012 [2 favorites]

If he's just a bit clueless, you can train him. Tell him exactly what you want. "When you come over tonight, I want you to bring six beers and a bottle of red wine. That's the price of admission."

But could it be that he's just too hard up? Make sure you aren't expecting a poor relative to contribute things he can't afford just so he can see his family. And if that's the case -- if he's too poor to share the costs -- either stop inviting him or accept that you're footing the bill.
posted by pracowity at 7:13 AM on September 11, 2012

There are some family members that are just very frugal. You can ignore it, but I don't think that's healthy for your familial relationship especially because it will probably lead to resentment.

There needs to be some sort of give and take in the relationship. Sometimes, people give and take different types of things, but ultimately it needs to balance itself out.

You should address this without making it into a confrontation. In order to do this, you need to act relatively casual about the situation, maintain a friendly tone, and ask rather than demand.

For instance, if your brother invites himself over to dinner then you could say: "Yeah, we'd really like that but can you please go to Whole Foods to buy dessert. I think everyone would enjoy it if you could bring something sweet to cap off the meal."

If you're having a picnic or a potluck kind of dinner then you could say: "I'm bringing roast beef with potatoes to the dinner tomorrow. What are you bringing?"

If you're going somewhere together then you could say: "Is it cool if you drive? I can get us coffee."

The important part is that he feels like contributing will be appreciated because you're doing something for him too. Your own family needs to feel appreciated by your brother and having him contribute might improve the relationship for all of you involved.
posted by livinglearning at 7:14 AM on September 11, 2012 [1 favorite]

4a) you either accept that you're feeding your sibling with nothing but their company in return, or you tell them straight-up they need to bring something (people do this all the time, it's not rude: "hey, I'm making X, can you bring Y side dish?")
4b) meet at the location and drive separately
4c) never forget to split the check; if it happens, make it clear you're going to split at the table (so bring enough cash to cover your bill+tip, but don't put out enough to cover sibling's).

You're not going to magically turn your sibling or anyone else into a generous person who reciprocates unless they want to change. If you want to involve them, you're going to need to either tell them how to meet their share or accept that your generosity will likely not be met in kind.
posted by asciident at 7:15 AM on September 11, 2012 [1 favorite]

-If I cook dinner for my husband, me, and sibling, the sibling never offers or shows up with anything to add to the meal. We provide the food, drinks (wine, beer), etc.

This is pretty normal. If I cook dinner for people, I don't want them to bring stuff. (Well, alcohol, fine. But if they don't, that's reasonable too. I assume you're not talking about a potluck.) The issue might be that your sibling never reciprocates by inviting you over.

-If we have a place to go (drive), sibling never offers to drive. In fact, sibling says that he doesn't want to drive to avoid the wear on his car & spending money on gas.

"Oh, that's too bad, we can't drive this time. I guess we'll go another time." Stop driving.

-If the three of us are out at dinner and forget to ask to have the check split, this sibling never reimburses.

So, you get the bill and what? You just don't ask him for his share and pay up without saying something like "Okay, 60$ plus tip, so that's 70 total which is about 23.50 each"? Because that's weird, otherwise.

He sounds cheap as anything, but you're also setting things up that make it seem like you're cool with it.
posted by jeather at 7:16 AM on September 11, 2012 [6 favorites]

The biggest problem is that you've set expectations by allowing this behaviour to continue for awhile rather than tamping down on it right away (like one would normally). Changing the parameters of the relationship now is going to involve some pain whereby the expectations are altered.

The best way to do this is to be up front about your feelings in a person-to-person talk, and then opening the floor for possible solutions. This is how adults approach differences in expectations: by having a simple, non-argumentative discussion about fixing a problem.

My advice is to attempt to approach it like adults. If you get a good solution, then yay -- pain minimized, change effected. (It may be that the sibling starts carrying a fair share of the load, or that the sibling doesn't hang out with you any longer by their own choice.)

If you are unable to find a resolution through adult behaviour, then -- to my mind -- that's a resolution in itself. I would not want to hang around someone who is unable to act as an adult. So would simply stop inviting them along.

Perhaps this is optimistic. I think it is better to approach problems optimistically, but with a contingency plan. Try being an adult about it together. If that doesn't work, be an adult about it by yourself.
posted by seanmpuckett at 7:18 AM on September 11, 2012

Nthing the whole "be direct or stop inviting" above.

I actually have/had a similar situation -- my boyfriend and I often invite our roommate (she now lives with us in a new place, but it used to just be she and I living together + him visiting) out to dinner, drinks, etc. with us. Bill would always fall to us, and typically he and I take turns paying for going out when it's just us. She would suddenly be looking around the room like she didn't know what to do with herself when the check came.

We tried "OK, we got the bill this time, next time we all are out together it's on you", which seems to be a reasonable thing, but can be awkward to bring up again during that next time, as people often forget/"forget".

We decided instead of just looking at the bill, we would discuss it out loud: "Well, the total is $X, and here are our entrees/drinks/bowling shoes/whatevers, so we need to put in that plus some tip, so $Y should cover it. And here you go JorlyRoommate, just subtract $Y... and now all you have to do is put in $Z!"

Also, things like "OK, this round of drinks is on me... JorlyRoommate, you got the next one, right?" She apparently did not understand how this fairly standard back-and-forth thing goes when friends go out to drink together.

Just make it super easy for them (no "oh, I had no idea how much I owed/that I should contribute things") and be as pleasant as you can... this makes it super awkward for them to refuse. Similarly, I like griphus's idea of splitting it three ways, even if you and hubby would naturally pay together normally.
posted by jorlyfish at 7:28 AM on September 11, 2012

I favor an "All of the Above" approach.

You need to cajole, you need to address directly, and you need to limit the ways in which this person can tick you off.

In situations when this person says something patently ridiculous ("I don't want to put miles on my car or pay for gas") you can just say something like "Oh, neither do we. Guess we will all just walk then."

You need to help this person see appropriate times to contribute by addressing them directly. As others have suggested, clearly your friend's internal barometer for when it is appropriate to contribute is... off. Lacking completely, possibly. Direct suggestions for contribution, when appropriate, are good to help along someone in this predicament.

And finally, instead of limiting these situations by not inviting this person, you need to limit these situations by reforming your expectations. If you issue an invitation, make it a true invitation. And if you can't issue a true invitation without the expectation that your guest will contribute, then don't issue the invitation.
posted by jph at 7:39 AM on September 11, 2012 [5 favorites]

You need to help this person see appropriate times to contribute by addressing them directly. As others have suggested, clearly your friend's internal barometer for when it is appropriate to contribute is... off. Lacking completely, possibly.

This. Your sibling might not even realize what's going on on your side of things. "Well, they invited me to dinner, so I don't need to bring anything/pay." Or, if you're not always inviting, it might just be "They usually just pay."
I'm pretty sure this was the situation with aforementioned roommate -- it was not malicious at all, just kind of derpy social skills. You're potentially doing them a favor... methinks there is a likelihood he is doing this to other friends as well.
posted by jorlyfish at 7:47 AM on September 11, 2012 [2 favorites]

Is this your sibling or your husband's? Maybe it doesn't matter that much, but I guess to me it would matter in who is the person who handles the situation, and might have just a bit more say in how it is handled. For example, if this is your husband's sibling, then he is the person with the long-standing relationship, and in some way it is more his business if he wants to pay for the sibling. I say that because you mention it is not about the money, that you have enough to cover him without it being a big deal.

If it is your sibling, then I say you should handle it the way others have recommended above, because he is your brother, and you need to straighten out the relationship on a deeper level, in a way you are comfortable.

You don't mention whether you enjoy the sibling's company, what he brings to the table besides cash, that would also have a big bearing for me, and I also think that would be your business to have input in even if this was your brother's sibling (who you choose to spend time with).
posted by nanook at 7:56 AM on September 11, 2012

Is this the whole story, because there really is no need to hang out with him just because he is your brother? What do you get from him? Does he have an area of expertise that he shares with you? Do you get enjoyment from his company? Why are you hanging out with him?

My expectation when I invite someone to dinner is that I will be serving dinner, and they will be eating. At some point in the future they either 1) return the invitation to a dinner in their home or 2) take me out to dinner. If neither of these things happen, I have to determine if the pleasure of having them at my table is worth the effort/expense of preparing dinner. I feel the same about a dinner invitation or event invitation, if I am doing the inviting, then I am taking on the cost/effort. There are some friends who do not reciprocate, but add value to my life in other ways, so I am willing to continue inviting them. There are other people, who used to be friends of mine, that did not reciprocate, and I realized that they did not add enough value to my life to warrant the effort/expense.
posted by hworth at 8:01 AM on September 11, 2012 [2 favorites]

I have found that some of my relations-in-law are slightly clueless in these regards, and if I want them to share the responsibly / costs of our gatherings, I have to tell them. They aren't intentionally taking advantage - they will help in whatever way they are asked, when they are asked.

I think this is a partly a function of different family cultures and partly archaic but entrenched gender norms. These fellows don't have spouses and in their family, women are responsible fir family gatherings.

If your sibling can't contribute as much financially, but it still sticks in your craw that he doesn't bring anything, ask him to bring dinner rolls.
posted by Heart_on_Sleeve at 8:12 AM on September 11, 2012 [1 favorite]

I have friends who do more than their share of paying, partly because they make hecka bank and I don't, and partly because they hate eating alone. The difference is that I always initially turn down an invitation and explain that I'm broke, and then let them offer to treat me if they want. Usually it's "Oh, ok! Next time, then!" which I'm fine with, but sometimes they're okay with paying.

Warn him before you start charging him suddenly. He might have money for video games on Oct 1 but by Oct 10 be broke til payday or something. Sibling/Friend is used to you floating him. If you invite him out the day before payday, and then spring a bill on him, it will be bad feelings for all involved.

If I were you, I'd say something along the lines of "Husband & I are working on getting more responsible about money and keeping track of it. We're going out to Restaurant tonight? Want to come? You'd have to pay for a third of it, if you do, though."

He answers Yes/No and you two do exactly what you want regardless. Meaning, don't change your plans if he decides not to come, and don't press him to join you.
posted by small_ruminant at 8:18 AM on September 11, 2012 [1 favorite]

Oh, and a couple inviting someone over to dinner is easier than a single, as I'm finding out, now that I'm part of a couple. I always felt awful about not reciprocating dinner parties, but as a single, in a relatively small and not well stocked apartment, it was DAUNTING figuring out how to entertain more than one other person. I don't know what the magic is, but now I'm part of a couple and have a regular sized kitchen at my disposal and we've had people over for dinner every month or so, it seems like.
posted by small_ruminant at 8:20 AM on September 11, 2012

If this is your sibling, then you have to just talk to him. Tell him that this is making you uncomfortable and work out a mutually satisfactory solution.

But I get the feeling that this is your husband's brother, not yours. In which case this is a more complex problem. It's really a problem you have with your husband, not a problem with his brother. You want your husband to put his foot down and he doesn't want the family angst. Personally, were I in that situation I would try to just make peace with it. It can be hard, even for a spouse, to really understand everything that is at play in family interactions. Your husband may have pretty good reasons not to want to raise this issue directly with his brother. And, in the end, none of what you're talking about is actually a significant financial burden on you, is it? It's not as though the six pack or the bottle of wine for dinner is anything other than symbolic--and the same goes for the odd unsplit check and the gas. Just look at it as a minor charge for family togetherness, and be happy that you, your husband and your brother in law are all getting along harmoniously.

Maybe, one day, the brother in law will get his life together better and start seeing ways to even the score. But if not, well, you're laying up treasure in heaven, as they say.
posted by yoink at 8:46 AM on September 11, 2012 [1 favorite]

You need to do this instance by instance.

Don't forget to split the check for instance--I am generally scrupulous about paying people back, but will forget if too much time goes by.

Ask the sibling to contribute a bottle of wine or a salad or whatever if you invite them to dinner.

Tell sibling that if you are going to carpool you need to alternate cars.
posted by mlle valentine at 9:06 AM on September 11, 2012

I have a dear friend, I love her to pieces and she is the WORST tipper ever. I cringe when she offers to treat because I know that she's going to undertip. Undertip is an understatement, she's basically going to stiff the server.

I used to leave a separate tip on the table, give her a head start and then hang back to leave it under a plate, or slide it onto the credit card tray or something.

The other issue was if we split the check it was always screwed up somehow that required me to pony up extra money.

One evening it came up and I told her to her face she's a terrible tipper, her daughter and son-in-law agreed, now she hands us the bill and we help her calculate the appropriate tip.

Turns out she's just terrible at math. (I don't know how someone could be THAT bad at math, but there you have it.)

She doesn't love us less because we told her, she's aware now, and asks for help.

You don't have to be mean to bring up the issue. I agree that you and your husband should have the conversation during a neutral time (not when the waiter brings the check.) "You know sib, can't help but notice that you don't contribute as frequently to our little get-togethers, what's up with that?"

The other thing is when you issue an invite to dinner, you can say, "Hey, we're barbecuing on Sunday. If you want to come, we'd love to have you, can you pick up some dessert on the way over?" Just be matter of fact about it.

Or have a pot-luck and let the Sib know. "We're providing ribs, Lisa is making potato salad, Mom's doing her famous beans. We've got dessert or beverages left, what would you like to handle?"

As for dining out, just be SURE to split the check.

He may just be out there, not intentionally trying to stick you for the expense. Don't assume the worst.
posted by Ruthless Bunny at 9:13 AM on September 11, 2012

This person is cheap and selfish to the core. I would outright tell them "look, we love hanging with you but either contribute for YOUR eatings to the bill or bring something small to our dinner outtings."

Sometimes, with family, just say it like it is. They're older than you and need to grow up.
posted by stormpooper at 9:59 AM on September 11, 2012

Oh wow - I totally feel your pain. My husband's brother is a pro at this. We're pretty sure he knows what he's doing but just.doesn't.care. He's gainfully employed, older than my husband and appears to have a busy social life in the city - i.e. he's not sitting at home night after night eating beans out of a tin worried about the lights being shut off.

He expects to be picked up and driven to our place (when there's a frequent-service city bus that is close to his place and deposits him at the end of our street) and pouts when he has to take transit. He shows up empty-handed for family dinners and then observes that there doesn't seem to be enough beer in the fridge. When we get tired of cooking during longer family visits and head out for dinner - oh, the awkwardness when the bill comes is legendary. Sometimes my in-laws, visiting from out of town, will pick up the whole bill to make the awkward go away, but they seem to enable him too, and we sometimes find ourselves stunned into picking up the tab ourselves. We snap back to our senses afterward and say WTF? to each other.

What we've been doing with differing amounts of success is what has been suggested already in the thread. We are trying to simmer down and forget about the history and just casually say "hey - can you bring a bottle of wine when you come for dinner on Friday?" or "hey - you noticed last night that there wasn't enough beer...mind grabbing some for tonight?". But then we will get blindsided by his protests sometimes - it's disturbing to hear a 40-something man whine like a young Luke Skywalker just because you asked him to take transit. We often wonder if he treats his friends like this, and sadly, the answer is probably no. It seems as though he's decided at some point that his money and time are more important than ours.

We realize too that we've "spoiled" him in the past and confrontation in this WASPy family is simply not done.

We are going to continue with our casual, situation-by-situation approach and so far it seems to be working - he did buy a case of beer when my husband and he went to a family cottage - we're not sure if it's because my husband asked him to, after realizing that he genuinely forgot his wallet in our car while they were in the beer store, or whether brother-in-law felt a twinge of conscience, but we're happy with the result, however slight, and hope to keep using this approach.

The biggest battle for us is to stay engaged and continually set those boundaries and have the presence of mind and, yes, courage, to ask for separate bills, or tell him he needs to take transit, or ask him to bring wine/beer etc when he's coming over for dinner, and to say no to requests for cab fare, etc.

And, yes, we realize that it's unfair that we have to monitor him like this and that polite adults don't need this kind of constant reminding, but that's just the way it seems to be shaking out in this family dynamic. I'm mainly writing this to let you know you are not alone, and it's okay to be really frustrated and angry about this, but I'm also glad you're talking about it and interested in changing the pattern.

Still, I love and plan to make this my family-thing mantra, from inturnaround's answer:

"It's not wrong to ask for fairness."
posted by champagneminimalist at 11:03 AM on September 11, 2012 [1 favorite]

Some of these replies make me sad. Sure, just cut him off! Obviously he's doing this on purpose and in spite of all the loving parenting he had that prepared him for life as an adult.

What you do, is ask him to bring something. You can start with wine/beer, sure, but start to leave it open-ended. "Can you bring something? We have the meat and potatoes, can you pick up some stuff for salad?" and eventually I bet he starts seeing this kind of thing elsewhere and starts to ask if there's anything he can bring. I was well into my 30s before I realized that my brother bringing wine to dinner came from anything other than his liking wine.

Restaurantwise, just split the check evenly and tell him his share, which is what adults do. No, don't micro-calculate shares unless someone's share is way out of scale (in which case they will likely have already volunteered extra money in some way), because that kind of thing usually ends in your early 20s.

Drivingwise, be blunt. "Hey man, we *always* drive. Either you drive or you pay for the booze." Something like that, with an edge of informality. He doesn't need more parents, just some friendly prodding to make up for their apparent failures.
posted by rhizome at 1:44 PM on September 11, 2012 [2 favorites]

4) Talk with the sibling, find out what his thought process is, share your thought process with him, and see if you can come to an agreement.

I say this because you seem to feel that fairness means everyone contributes equally, but the sibling may have a different definition. You write:

This person doesn't have tons of money, but he does have plenty of disposable income that he uses for video games or other media (tv shows on iTunes, etc). Thankfully, he never asks to borrow cash money from us.

I'm inferring from this that while he isn't destitute, he has a lot less money than you and your husband. So maybe you and your husband can spend as much disposable income as you like on personal entertainment, AND have money left over for socializing, while the sibling has to pick and choose.

You also emphasize that he's an adult - implying that "adult" trumps "poorer sibling" when it comes to everyone paying for themselves. Most people would probably agree with you there, but keep in mind that this is a culturally specific idea and not the only "right" way to look at things. When AskMe gets questions about financial imbalances in romantic relationships, things look different: a lot of responders say that if the wealthier partner can afford to pay for the poorer partner, then why shouldn't they? Is it possible that the sibling is applying this guideline to sibling relationships?
posted by Mila at 2:58 PM on September 11, 2012 [1 favorite]

Be blunt. We're having dinner, you bring beer. If he shows up without it, no beer for him. "Sorry, last two bottles." If he whines, keep repeating, "Sorry, we told you to bring beer."

Tell him you're going out. If he want to go, he needs to drive and meet you there, or pick you up and you'll all go together. If he doesn't want to drive, fine--sorry, he's uninvited/guess we won't bother to go (with you along.)

ALWAYS split the check. Or just roughly divide by the number of people at dinner. If you forget, then suck it up, but tell him he OWES x dollars in tip. Ask him if he wants to go out, and BEFORE you leave tell him it's his turn to buy.

You need to be right up front in telling him what you expect prior to meeting with him. Don't tease, don't cajole, and don't spring any surprises on him.

It doesn't sound like an ask vs guess thing, it sounds like a mooch. He can only mooch if you let him. Only give what you're willing to give, and if it doesn't get better, stop hanging out with him so much.
posted by BlueHorse at 4:26 PM on September 11, 2012

Is this your husband's brother? And what are we talking about here -- an occasional six-pack, gas money for an outing, and only the checks you forget to have split? Jesus, let it go. Let your husband enjoy his brother.
posted by palliser at 7:03 PM on September 11, 2012 [2 favorites]

I know I'm going against the grain here, and I'm not trying to suggest that anyone is wrong in any way for applying these standards, but I'd like to point out that these expectations are not universally shared.

I am part of a couple, we're doing relatively well. If we invited a less-well-off close friend to dinner with us, I would be mortified if they brought something that was expected to be part of the meal. The implication, for me, would be that we were too poor to be able to adequately plan for guests, and too stupid to realize it.

So I almost never bring food gifts when I visit people for dinner. Instead, I reciprocal-invite them if I can. On these occasions it is my job to treat. But again, as I said, I'm fairly well off.

You say that you see your friend spending disposable income on video games. But do you actually know down to the dollar what he spends? He may be spending on used games. The total budget may actually be less than an eating-out budget would be.

And here's another thing to remember: who is doing the asking for these excursions? Is it possible that these are excursions that friend/sibling would normally never engage in or spend money on, but is going in order to go with you? Perhaps at home he lives pretty frugally, but you have nice dinners. Or perhaps he wouldn't drive or use gas to go by himself, but if you're going and are willing to take him, then he's up for it. Or maybe he doesn't have a large eating-out budget.

I think that before you can think of how to change his behavior, you need to think about these questions. And also some more for you:

Would you be happy if he started issuing reciprocal invitations, even if they weren't of the quality that you generally engage in?
Would you be happy to eat the food he generally cooks for himself?
Would you be happy engaging in the entertainment he enjoys on his own?
posted by corb at 7:12 PM on September 11, 2012 [1 favorite]

Change the way you socialize with the person?

I don't meet all of my friends at the same restaurants. Some people are fine with $20-30 per person, others would prefer dollar menu options.

I don't invite everyone into my home. If they never invite me to their place (for whatever reason), then I just stick to meeting them in public.

Some people host 100%, so I don't bring anything to their place and they don't bring anything when coming to my place. Others host by potluck, so I keep some staples on hand to bring to their place and incorporate whatever they bring to my place.

If they never spend any money, only socialize with them in ways that do not involve reaching for a wallet -- public libraries, parks, free concerts, fairs, people-watching at the mall, etc.

If they never travel more than XX miles out of their way, then pick acceptable locations or times when they are already in your neck of the woods (and likewise).

Basically...just socialize with them on their own terms. Let them set the pace. With some friends, that might involve being given half a bag of microwave popcorn and a plastic cup (originally from a convenience store) filled with generic cola poured from a 2L bottle. I give them something similar when they are visiting me.

In summary: I have no issue socializing with people who are dirt poor or simply want to behave frugally. But if people don't want to socialize with me on these even terms, then they were not interested in my company and only wanted a free ride.

Caveat: Sometimes a relationship is clearly not on even footing but for whatever reason it is important to one person that it be maintained. For these times, I simply treat them and consider the whole occasion as a gift. There's no mental tally or expectation of reciprocity. But I also don't consider these purely "fun" occasions -- more like keeping lines of communication open, limited to once a month.
posted by 99percentfake at 8:06 PM on September 11, 2012 [2 favorites]

Oh my God, let it go. It does sound like you're talking about your partner's sibling, not yours. If your partner wants to be indulgent, so be it -- who cares?

You're not the sibling's mother and it's not your job to police his behaviour or to ensure he's appropriately socialized. Maybe he has Aspergers or was spoiled or deprived as a kid or has significant expenses you don't know about. Sure, he probably doesn't, but how does it hurt you to assume the best about him, and to be generous? (Maybe read this, if you haven't already.)

You are lucky. If you were broke you would need to nickel-and-dime him, but you don't. So why do it? Just be kind, and let your partner enjoy time with his sibling. Don't make up problems where there's really nothing wrong.
posted by Susan PG at 1:43 AM on September 12, 2012 [1 favorite]

Change the way you socialize with the person?

I want to highlight this because it is an awfully good answer. I stand by my own observation -- that he's not going to respond to "subtle suggestions" that he change his behavior. However, instead of having social gatherings with him that are the sort of things you would expect from an adult peer, do stuff with him that's more "on his level" and closer to his financial/social limitations-- eg, invite him over to play video games with your husband, go to a street festival, or go to some free local event in the park.
posted by deanc at 6:19 AM on September 12, 2012 [1 favorite]

I second the 'change the way you socialize' answer.
I had a lodger who took the p so much it was insane.
She never once, in two years, offered to even help cook or clean up after a meal she shared with us. She never bought a drink, offered any help, offered any contributions, or even thought about doing so as far as I could see.
I did the 'can you bring a bottle?' thing, and she didn't bother.
I felt embarrassed, annoyed, angry, bemused, and in the end, just really fed up, and I asked her to leave.
If someone can blatantly ignore basic rules of etiquette, you either just have to tell them, on the spot what they have to contribute, or you just stop inviting them to take the p. Or accept that they're way too self-absorbed to give a shite.
posted by MonkeySoprano at 7:16 AM on September 14, 2012