I used to have a good mix of both - friends that made about the same as me and friends that made way less. As the years went by, I found that the friendships with those that made way less faded. We just ended up with less in common. I wanted to go to swanky clubs, they wanted to go for $2 beers. I send my kid to one of the best private schools in the state, they argue that the public school system (ranked in the lowest five in the country) offers a great education. I live in one of the nicer areas, they argue with me that they're fine living next to a crack dealer. I'm not comfortable bringing my kid in the area they live, they call me a snob.

I never had an issues with who picked up tabs, partially because they knew I'd do it if I had the money. Meaning, if I didn't offer don't ask. My bills are probably in proportion to theirs. Yes, I make more, but I also have a mortgage, two car notes, private school for my son, healthier foods for him, office expenses, etc. They have cheap rent and lots of credit cards. In the end, I probably ended up with a bit more discretionary income some months but about the same others (I work on commission). Our income allows us to afford better things for our family, not for our friends.

If they were expecting me to pick up the tab every time, I'd say something. I'm really blunt and honest though and that's just how I go about things. I'd probably say "just 'cause I make more doesn't mean I need to pay for you" and however it went over it went over. Doing stuff like that doesn't work for most people. Maybe something like that, but a lot more gently.

Alan & I have always bounced back and forth on both sides of this fence and it's always been a sticky situation from either side. On the well-off side, I never minded helping out friends or paying the tabs because it was usually our idea to go out (or lend them some cash) in the first place. But when a few of them started acting like they expected us to do that all the time, it was a different story. They didn't feel as much like friends any more as they did leeches.

On the poor side, I always felt that if any of our friends were too snobbish to accompany us in places that we could afford, or come for dinner/drinks at our home, they weren't any better. That felt like they were more interested in their high opinions of themselves and their statuses than being friends.

I have the same problem. I end up paying for wayyyyy to much. I can't even count how many people I've helped out and paid for. I make it a rule now not to pay for anything for anyone.

My friends all are probably making about as much as me. We never pick up the tab for anyone else when we go out, and no one does it for us. We do have one friend who was doing pretty badly for a while, but he declined offers for lunch or dinner.

Tell them to pay for their own shit.

I used to be able to pay for friends' dinners, but things have gotten tougher for me. Thankfully they've all been understanding and usually pay for their portion without talking about it. They seem grateful for the times I payed in the past, instead of expecting it to be routine.

I say speak up and insist everyone pay for their share, especially if it's not even a special occasion or something and just hanging out.

Say something,its your money you earned it.its one thing if you offer 2 pay but its another when they dont offer at all 2 help.

I can be in both positions.

I think you're being too nice. Even when the person makes 10x what I do, I at least offer to pay or at least help.

On the other hand, I've paid for things for others, but it's never been "expected". It's something we talked about before hand like, "I wanna go to X place" - "I can't afford it, sorry" - "It's okay, I'll pay for it", or just random annoying acts (regardless of incomes) of kindness or whatever.

Honestly, I would think the best option is to STOP going out like this instead of risking your friendship. You guys don't HAVE to go out to eat do you? Just have them over. If you're tired of paying the bill don't go. Ask them over and cook for them... unless you don't want to pay for it. Come up with other plans of hanging out. You could all have a get together at home and just bring it up, make plans and say "hey, if you cook dessert, I'll do the hamburgers." or whatever. We have a lot of parties at my house and that's kind of how it goes. For a long time, everybody expected us to do ALL the cooking, buying and everything and finally we called ahead and asked each of them to do something. I usually say "I have to work and only have time for making the dessert, can you buy the drinks?" Of course you have some people that bring a can of damn corn and green beans at your christmas party, but hey. It usually works out.

Maybe it's just me, but I have this "if you can't say it or do it 100% nicely then you shouldn't do it at all. Of course that doesn't mean there aren't times to let someone have it or stand up for yourself, but it seems there are plenty of other options you can try before hurting feelings. They truly may not realize that it upsets you so badly. It does depend though... are you the one making the plans and asking everyone to go out each time? If so, that is probably one main reason they expect you to pick up the bill. If they are the ones making the plans to go out, simply say "I just don't have the extra cash this week, I'm saving for something or catching up on bills."

If your friends do this to you all the time, any time you go someplace and seem to carelessy take and need and want then I'd be pissed. We have a friend of the fam who my sister kind of brought into our family years ago and she's... well... a serious damn bum! She comes in the house and will take anything and everything from the entire can of coffee to every Dr. Pepper in the house or cleaning supplies. Once she saw some gardening supplies and said "I've always wanted a garden.." she took everything we had to make her damn self a garden. Then decided it was time for a new washer and dryer so she chunked hers and went to the church and before the month was over with, she had herself one hell of a nice washer and dryer. Her husband makes really good $ too! That is a user. If that's how your friends are treating you, I wouldn't say anything to them about helping out, I'd get rid of them before they suck the life out of you... and your wallet. I guess it's hard to really say unless you know the person. Only you know them. I hope everything does turn out for the best though.