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Dear Sugar
Whenever I go out with a group of friends, one of the gals in our crew never contributes to the bill. She always keeps her hands in her pocket or she pretends to be searching around in her handbag for her wallet until all of the cash has been collected.

We know that she makes a great living, so it's really awkward that she never offers to pick up so much as a round of drinks...ever This behavior is getting old quickly and I think it's time to confront her, but it's always so funny when you're talking about money. Do you have any ideas on how to approach this? Chagrined Cheryl

Dear Chagrined Cheryl
Keep your distance from the check the next time you are out. See what happens when the time flies by and the bill just sits there. After a fair amount of time if she still says nothing or doesn't pull out her pocketbook say something like this:

"Ok, girls, let's settle up this check. Everyone owes "X" amount and that also includes the tip. If you (point to your friend) don't have cash on you and you want to pay with a credit card, that's ok."

This will put her on the spot and once everyone's shares are all out and paid, she'll have no choice but to dig into her wallet. If you are feeling frustrated, you could even ask her to cover your portion since you payed for her drinks the past several times you've been out. It's a little passive aggressive, but at least it's out there.

She will probably get embarrassed. She may even get angry, but that's the price to pay for being cheap. After all, nothing ever comes for free! If she claims that she doesn't know what you are talking about then just call her out on it. At least now you've brought the issue to the table.

Ms_Magnificent1 Ms_Magnificent1 10 years
DearSugar's advice is on point!
lickety-split lickety-split 10 years
marci, that is funny! :ROTFL: i had a friend that always assumed i would pay for her if we went somewhere. hello, it's not a date! i'm bringing naughty back :naughty_elves:
Marci Marci 10 years
It really is surprising how many people will try to get out of paying anything when a group goes out. I just never understand that. My group had one girl who would order appetizers, drinks, an expensive entree and dessert, and just after finishing her dessert would start talking about how tight her financial situation was. Then when the bill would come she'd get a pained expression on her face and people would feel sorry for her and ask her for like $10 and leave it at that. But she never hesitated to buy herself anything. After awhile when we'd were making calls to get everyone together again, I mentioned to her that we'd love to have her join us but we couldn't keep paying her way, and if she couldn't afford it, we'd understand. She was insulted and has never come again. And no one has missed her.
Vsugar Vsugar 10 years
Yeah, I think that everyone should pay for what they bought - There are some people who will whittle that down to pennies, like, "YOU owe $26.32, including a %20 tip", which I think is STUPID, but I once went to a dinner thing at a restaurant where everyone else was ordering $50 appetizers and "keep-'em-coming" cocktails- I had a salad and ONE glass of wine, and they tried to get me to pay my portion - $80!!!!! I HAD to put my foot down. It was EXACTLY like that Friends episode, where they all fight about money... I think it should be a given that everyone pay for what they ordered.
lolak lolak 10 years
Yeah I had two GUY friends who would do this all the time, I mean I know we asked you if you wanted to tag along but if you know you don't have the cash to pay your part then say so or at least casually decline. One of them is a teacher now and we have been best friends for a really long time so now that he has the money he pays for a lot of our dinners and outings so that's great, I always offer to pay my part regardless of what he says and if he won't let me I'll at least pay the tip. The other guy was slowly forgotten, no one wants to feel like your taking care of a grown kid. It's not your responsibility
JessNess JessNess 10 years
Whenever I go out with friends we always just pay for our own meals- that way everyone is responsible for what they ordered. Then everyone just contributes a couple of bucks to the tip. If you are going to a place that does family style meals then you divide the bill up equally between everyone. But it honestly is as simple as just having everyone pay for their own meal- do separate bills if you have too
justjaime27 justjaime27 10 years
Good advice, dearsugar! I used to have a friend like that...we'd all go out with a bunch of friends, and my husband is very generous so he prefers to pay, but when it came down to just the 2 of us going out without my hubby, it's as if he spoiled her, so she'd never even offer to pay her drove me NUTS! So finally, I would just give her the bill, and ask her "what I owed", I pretended to be bad at math...ha ha. That way, it casually forced her to pay her part... :) It's not like I CARE so much about taking care of friends' drinks/food once in a while, but when they start to ASSUME and EXPECT it, that's what ticks me off, you know? Oh, and don't forget the friend who thought her "BIG BOOBS" would just take care of the bill...she'd order whatever she wanted, thinking, "Oh, I'll get some guy to cover it"...and while yes, it worked for her sometimes, the other times I ended up paying for her, because "She was broke". If you're BROKE you shouldn't be ORDERING like a crazy rich lady!!!! lol It just amazes me. lol
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