Well not really where she comes from but where we still are?
Background, a group of us, 5, have been mates since school, now late thirties. We are all very close and regularly socialise together, nights out, weekends away, tea at each others houses. Financially we are all on the same level. Over the years all of us have been on benefits for short periods of time, worked, been unemployed, been SAHM and WOHM. Currently we are all 'comfortable' by that I mean bills are paid and theres a small amount left over for spends.
One of us, i'll call her Jane, came into an awful lot of money 4 years ago. Like lottery type money (she didn't win the lottery but the number is in the millions). A lot changed for her, she moved out of the area, quit working etc etc. But we all stayed mates, we still did the same things we've always done, she was still Jane but with a fuck load of money 
Roll on a few years and Jane seems to start forgetting that whilst she now doesn't have to worry about money, we still do. So she suggests to go away on longer holidays, different places we would usually go, weekends at more up market spas etc. Mostly we explained that we couldn't do that and she was fine with it.
More recently though she seems to be forgetting/sulking that we can't do it. So lots of 'god its not that much money' 'cant you just save' 'what about if we book it early then you have longer to save up'. We've explained over and over that it doesn't matter how long we've got, you can't turn centre parcs money into Ritz money
But she seems to be pretending or genuinely has forgotten what its like to struggle for money. For example tonight we are going out for drinks as we do on a monthly basis. Mate 1 mentioned on group chat she didn't have much cash so wouldn't be out late/would be getting the bus in. Jane has text to say 'surprise girls, managed to get a table at x for cocktails, meet you all there at 8'. X is a cocktail bar/resturarant that we would usually go to for a big once a year celebration as its bloody expensive £14 cocktails and upwards. Mate 1 replied on group chat saying are you having a laugh I can't afford that, Jane said 'ofgs its not that much, come on it will be a laugh i'm bored of y place'
Its the constant requests to do stuff that she knows we can't afford. I get that shes , by her own admission, bored. But we still need to work and look after the kids and parents and pets etc. Its getting hard to know what to say other than 'you've completely forgotten where you come from pull your head out'!
Mate 1 has text me privately asking if she can borrow and extra £20, which is fine we all lend each other money occasionally, but she feels like crap about it.