I hope she knows it’s there and doesn’t send the coat to the dry cleaners!
True that CC settings present unique challenges by their nature.
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When we’re out with the kids, we usually pay but lately my oldest and her husband have been picking up a fair share of the tabs. The caveat is that my DH does not drink and he gets a little salty when there is a bar tab from the kids (& me) that he picks up. He doesn’t say anything in the moment, but laments to me later. My response to him is always to have the kids pick up their own share of the bill (which they are totally willing to do) but he would never do that - he just likes to vent about it.
As I said in the other thread, my DH is a chronic picker-upper of the bill - especially when he sees his tablemates struggling to split the bill (drives him nuts) so he’ll just get out a CC and tell the server to take care of it. Drives ME nuts. Also, when he’s visiting his parents, who are very well off, he picks up every restaurant bill.
My algorithm is this: I pick up the bill when I am out with my kids (without DH). Older D reciprocates and I am hopeful that once younger D gets situated in her adult job next month, that she will also start to offer to occasionally pay. When I’m with friends, we usually agree to split checks equally even if the meals weren’t exactly equal - a few dollars here and there isn’t a big deal to us. It helps that pretty much every restaurant has the capability to split one bill to different credit cards. Doing it evenly (I think) is less of a pain for servers. Trying to break down a bill with everyone throwing cash in is maddening.
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I know I’ve mentioned this before, but we (almost) always and will (almost) always buy meals for our kids. They’re my kids and I want to always take cafe of them, even when they’re 70. They’ll always be my babies. My parents and in-laws do/did the same for us.
The almost in parentheses is because of course it’s not a 100% rule. When my Dad turned 80, I wanted to have a big (for us) family celebration. My sister and I split that bill. My kids haven’t been around for our birthdays since becoming adults, but I could see them doing that someday. And now we do pay for FIL when we take him out for breakfast. But those meals only happen because H calls him up and says “we are coming to take you out for breakfast.”
We don’t host hardly ever and vice versa. We have stayed with one Gf’s family a few times and they’ve come here once. With them if we go out, we pay. We also try to take them for ice cream. When they were with us, we went out more often because I don’t cook like they do! They paid once and we insisted on the rest.
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I also wanted to add that I get uncomfortable when people offer to pay for something FOR me and I therefore assume that they also get uncomfortable when I (or my DH) offer to pay (except for my kids, who love it - lol). I realize in all or most cases it’s a nice gesture, but it still makes me feel uncomfortable. I wouldn’t agree to go someplace, if I couldn’t afford to pay for my share. This is one of my toxic traits and I own it 
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My DIL used to be really uncomfortable because we paid for all meals out. My son will throw out his credit card occasionally but we almost never let him pay. For Mother’s Day their gift to me was supposed to be flowers and they were going to pay for brunch. But it was an expensive brunch I picked, and we wouldn’t let them. My son tells her “I’m going to inherit it anyway, and it makes them happy.” The one time I remember them insisting is when we had Christmas Eve dinner at their place, because they really wanted to host it. They would not let us pay.
It was funny when we took the kids on vacation last year, with a new to travel with us SO. At the start of the week he’d order a burger and didn’t want to pick any special beer or whatever he drinks. At the end he was having the double lobster tails, an appetizer and dessert.
I did give my step-d a little lecture after the fact when we bought her expensive shoes ON Father’s Day, and we’d taken her out to a nice dinner the night before. After shopping for her shoes, we went to a little sandwich shop. She didn’t even offer to buy her dad a cookie. I told her she really should offer to pay occasionally, especially in a situation like that. I also told her she should treat her mom occasionally.
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My husband is that person who will order the least expensive entree if someone else is paying.
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My father-in-law has long since passed away, but his practice of inviting us was with caveats.
He picked his favorite steak restaurant and he would pay.
(My family traditions were very different. Because of our income, my parents could never afford to take us out.)
So I was a little bit surprised when I was not allowed to order what I wanted the first time I went out with my FIL.
I’m not much of a steak eater, so I was unfamiliar with the cuts and how to have my meat prepared. My parents had steak, infrequently, but prepared it perfectly at home
Plus, I had been schooled, by my parents, to never order the most expensive thing on the menu. I happen to like chicken, so I always ordered a meal with chicken. Imagine my shock when the following occurred.
My father-in-law heard me order the chicken and told the waiter, “no, she’s having the prime rib”. My husband flinched and grabbed my hand with a gentle squeeze under the table. I told the waiter, “I really prefer the chicken and won’t be eating any prime rib if it is served”.
The table went silent. My husband said, “I’ll take her prime rib”. I looked directly at the waiter and said, if you could just start my own separate check, I would be happy to pay for it on my own”. The waiter smiled awkwardly, said “as you wish” and immediately left the table.
My father-in-law was really angry. So I looked at him and I said, “I have no intention of disrespecting you. It was nice of you to order the prime rib, but as I am unaccustomed to ordering certain meats, I would just prefer the chicken”.
My father-in-law was accustomed to telling people what to do in his company, and did that with his family. He had a significant income. He also knew that I was from a lower income bracket.
My mouth has gotten me into a lot of trouble at times. My parents always taught me to speak up for myself because no one else would.
My father-in-law was from a different generation and I now understand how he ran his family. But I was 28 years old and I had never had anyone reject a meal for me. If I had had common sense I probably would’ve just said OK.
But my husband said one of the reasons he married me was because I always spoke out for myself.
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@aunt_bea - I think you were right. You knew what you preferred ordering (the reason doesn’t matter) and your FIL had no right to override that. I’m glad you stuck up for yourself.
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He was quiet for a while and then when the meal came he started talking more.
After that, he took us out often and learned to “suggest” favorites.
My husband thinks that my father-in-law had to process that I didn’t come from a lot of money.
Later, my husband told me that his father said that I was his favorite daughter-in-law.
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My MIL and FIL cooked quite a few meals for is but didn’t go out to each much. We had them come to a few meals for celebrations where the menu had been pre-ordered.
I’m not fond of anyone ordering for me most of the time but will quietly put up with it if it’s an initial meeting. I am happy to discuss the options with folks who have been to the restaurant before.
This describes my husband. But if I dine alone with my D or S, I let them pay. 
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As I am kosher style, I can’t imagine someone ordering for me. That’s different if it’s someone I know well. Even in a fish restaurant, I don’t like swordfish or such.
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A friend just stayed with us for three nights. In part to visit, but also to attend a wedding that did not involve us. We cooked one night and went to brunch which she paid for (we offered to split the check). At lunch the other day we each paid for ourselves.
At times I have visited her because she was not able to travel due to family challenges. Because she wanted me to come and I paid for a flight and rental car, she covered the meals we had out (although I always offered to pay).
It really depends on the circumstances. If we are staying with friends, especially at a vacation home, we would pay for at least one meal and pay for groceries. If someone visits us, I don’t tend to pay for the entire meal out (since we are typically cooking at least once and providing breakfast, lunch, snacks) but would always offer to split the check.
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We had friends (not close ones) come last year. We took them up to our cabin. Ahead of time, they said they would pay for groceries, but they never brought it up during the trip, and I wasn’t going to ask. They paid for one meal out, but we split the check the rest of the time.
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That wouldn’t sit too well with me. Especially if it is people we don’t know that well, we would make an extra effort to show appreciation, and if we’d said we would buy at least some groceries for example -which we always would in this situation- we definitely would!
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I guess my guiding principle would be that no one should walk away from the meeting/vacation/meal/etc thinking “Gee, if it’s going to be like that I don’t want to do it again”.
A lot of it is simply the financial situation of the couple/family/group. Which can also be a point that drives where you’re going for the meal. If someone invited us to a dinner at a nice restaurant I would go into it expecting to pay my portion of it but not the whole bill - and if someone else picked up the whole bill “no, no, we invited YOU” - that’s fine.
Neither of my kids have hit “adult money” status yet but even when they do I find it unlikely I’d do something with them and let them pick up the check for a meal. Will I pay for their family vacation when they get to that point? Likely not.
We have close friends that we pretty regularly go to dinner with and 80% of the time we do a 50/50 split or occasionally one will pick up the whole thing… we figure over time it’s likely all washing out close to even.
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I’d like to think I could be assertive enough , when at market, to nicely ask , “is this the time you are buying the groceries?”
Said in a way like “bless your heart”.
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That was probably part of the problem - I bought groceries before they arrived. I should have just said, “Hey, if you could pitch in $X for the groceries I bought, that would be great!” Oh, well, I will the next time something like that happens.
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Close family members are a confounding factor; I think it’s whoever gets their credit card out the fastest. Life-long friends? We generally try to keep track of who’s “turn” it is. One big mistake I will never make again is pay for a neighbor’s meal in return for gas money which made her (it was a woman) feel like we were on a date (we weren’t.) I’ll never forget the annoyed look she gave me.
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We don’t keep track. We just divide the check. It all comes out in the wash. Sometimes they have more expensive options and sometimes we do.
I’m not an alcoholic beverage drinker, so I just get a fancy dessert.
It all works out with close friends.
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