I like having wine with dinner and a nice main course. If I go out with someone who is a water and salad person, and I clearly spent a lot more, I would generally just pick up the check rather than trying to split it.
It is awkward sometimes when I go out with another couple and I am single, when the bill comes the guy would pick up the check. I would either pay for it next time or I just carry cash with me so I could throw enough on the table if they were paying it by CC.
My extended family often go on vacations together and it would be 15+ people at meal time. We would have one person pick up the bills and then true up after the trip. We all know each well enough that if one person wants some expensive wine then he/she would pay for it (and then we all get to drink it too 
)
Just boggles the mind.
We took our extended family on a weeklong Alaska cruise (staterooms with balconys). As olders s’s wife was too pregnant to go (the cruiseline’s rule), DS invited his old college roommate (from 10 years ago, now very gainfully employed) to come, since the stateroom cost was the same for one vs 2 (except extra taxes, etc). You guessed it, the roommate never even offered to buy us a drink, or a cup of coffee before we went to the Rock N Roll museum in Seattle after the cruise (Great museum, by the way). Oh, and he managed to dovetail a business trip to/from Seattle from his hometown some he didn’t even have to pay his airfare to get to/from the cruise. I am not even sure if he thanked us for the free weeklong Alaska cruise. Does this one win the prize for ultimate tacky cheapskate?
Let me repeat one of my favorite lines. I read it in Dear Abby, but I’ve been corrected here before as to the original source. Anyway, it goes like this:
“No one can take advantage of you without your permission.”
Sorry, but someone taking advantage of me to the tune of $250 is someone I would no longer consider a friend. And if the question came up, I would be up front. And even if they did eventually be shamed into repayment, I would consider the friendship irreparably destroyed.
Who needs friends like that?
Perhaps their card was maxed out at the time. They did an incredible amount of shopping while with us including no less than 11 new pairs of shoes from DSW. If they were to visit again and ask me to pre-pay for something I would say -no, I didn’t get paid back last time and am not comfortable doing so again.
That would be my response to OP’s friend- look you keep bring up the fact you owe us money but don’t follow through. What’s up?
My parents once loaned money to an adult nephew who was starting a business. The business failed, and he started avoiding my parents ( something that irked them considerably). I believe they sent him a letter indicating their disappointment that the relationship was suffering. He eventually responded with a plan to pay back the loan in increments with substantial interest penalty should he fail to deliver. He failed to deliver.
Much later ( 5 + years) he sent a heartfelt apology, complete with a check for a sizable amount – much more than he could afford. My parents made the decision to return his check and mark it “loan paid in full.”
He has been an involved and loving nephew ever since, providing caring emotional support to my children and assisting me upon the deaths of each of my parents.
He remains enormously grateful that they were able to forgive his failures and welcome him back.
That’s the bad part IMO. If the guy was invited, he was invited and shouldn’t be expected to buy everyone coffee or whatever (though a gesture like that would certainly be nice I wouldn’t expect it). Combo with work trip to get free airfare is just smart 
But not saying thank you? That’s bad.
@OHMomof2 - while I have no idea exactly how my DS worded the invitation with his former roommate, everyone on this cruise was our guest (there were 12 of us). We were clear with the guests that we covered their airfare and the cruise stateroom (and one additional private meal in an upgrade dining room was included). We were not covering any additional cruise ship expenses (no incidentals, onboard purchases, etc). Some (well, DS #2) bought rounds or drinks or a bottle of wine on more than one occasion on the ship. When we ate out on the excursions we chose to be clear that each was responsible for their own food. We did pick up the cost of museum entrances for everyone, but any selected excursions were paid for by the guests themselves.
I am sorry, but its just rude/cheap to not even offer to, as a thank you, to offer, at the very least, to buy a cup of coffee or a snack at one of the ship snack places or on an excursion or what have you. I wasn’t raised that way. If someone does something nice for me, I turn try to repay in some way or at the very least show my gratitude. Oh, and the roommate/guest not only signed himself up for a few massages (his expense), he knew that I’d gotten an extra coupon for a discount on a massage that I wasn’t going to use, so he asked me for it. Really, its rude not to even offer to buy someone who has spent thousands on a free trip, a cup of coffee. I would be mortified if my kids didn’t show their appreciation for such an offer of kindness. And it’s not like this roommate was 12. He was 31. Has a nice apartment, a good job, etc.
My husband and daughter just took a spring break trip and stayed in a condo just bought (so there was no lodging expense to speak of). She brought a friend who constantly offered to pay her own way or chip in somehow. He never let her, but when he was dropping her off on the way home she had her mom waiting with a thank you card and gift card waiting for us. That was very gracious I thought and we wouldn’t hesitate to host such a thoughtful girl again. We have three kids and their friends never pay when we invite them somewhere although it is nice when they come to our cabin and bring something to eat - it always gets eaten!
EXACTLY, @threebeans. That was very gracious of your daughter’s friend, and her mom. I thought at the very least, with no offer of any kind, that maybe we’d get a thank you note or something. Nope. Nada.
At the coffee shop after the cruise (HE selected the coffee shop) there were 4 of us. DH, DS#1 his roommate and me. Not even offering to buy a cup of coffee after this cruise? Really?? Sorry- thats cheap, tacky and rude.
@jym626 - you probably paid for the cruise because of a special family occasion. It would have been nice for the young man to order few bottles of champagne to celebrate the occasion.
Thank you, @oldfort Yes, this was a family occasion/celebration and the roommate/guest knew that. He bought himself plenty of drinks on the cruise.
And @OHMomof2 , I never said I EXPECTED him to offer to buy a drink or a cup of coffee, but was, TBH, surprised that he never even offered. Terrible manners, IMO.
Do you think he wanted to come on a family cruise? No offence but that all sounds like torture to me, but I would just have declined. This was someone in their 30s, right, not a kid?
It really wouldn’t be that big of torture if it is mostly young adults. When we go on a family vacation, it would be 6 parents, and rest of them from 25 to 30. Not exactly torture, especially if they don’t have to pay for anything.
@Sybylla - 6 of the 12 were DS #1, guest, DS#2 and then fiancée (now wife) and 2 nephews of the same age as my kids. So 6 of the 12 were all the same age (late 20’s-early 30’s). They had a BLAST, did much of their own thing, hung out in the hot tub, went to shows/watched movies/watched game of thrones on my ipad on one of the stateroom balconies. Torture? Hardly!! Good heavens.
The ship was huge and aside from dinner, occsaional lunches together and signing up for some things like wine tastings on the ship, we didnt see them all that much. Saw DS 1&2 in the gym. The guest was having one of his massages. SIL and her friend the at the earlier dining time so we didnt see them at dinner. So dinners were 6 of the 20-30 yo’s and 4 older folks (us and BIL and spouse). The guest was a big photography nut, and we did walk around the decks with him as we cruised through the glaciers. He is perfectly pleasant (if not a tad full of himself, but oh well). And he had a great time. I think he came on one excursion with us (whale watching) as DS#1 and 2 came with us on that. And all of use went to see the totem poles in Ketchikan.
(The other 6 were Myself/DH and his siblings/spouses. Actually. SIL is single- she brought a friend who insisted on paying her own way).
@jym626 - maybe you should have paid for the young man to go. Oh wait, you did.
If I don’t plan to pay for others, and no one says ahead of time that they are picking up the check, I’ll just suggest separate checks when the waitstaff arrives to take our orders. Saves a lot of hassle.
My mil would say EN-TI-TLED! 3 syllables, drawn out. One of her favorite words for ungrateful guests.
Agreed. a thank you, coffee, whatever, is what I taught my kids to do.
However, I haven’t been in your place, bringing along kids’ friends on a family vacation, so I’m not sure what I would expect. They’re my invited guests so I suppose I’d plan on paying for everything (or whatever was arranged ahead - sounds like in this case you provided lodging/cruise and they were to pay for all else).
I’d certainly expect a thank you. From an adult, a bottle of wine or something similar would be nice.