We have some friends who are tight with their money- think the type that wear designer clothes, shop at m&s for their food, but never go out or on holiday. We are reasonably well off compared to them because both DH and I work, whereas they are less well off because the DW has been a SAHM for 16 years at least! Yet they spend their money on designer stuff, whereas we don't but enjoy eating and drinking out and foreign holidays.
DH doesn't want to go out with them because he says he always ends up buying all the drinks or paying for dinner. They have form for accepting the first round of drinks which DH pays for and then declining a second drink. DH will also offer to pay for dinner, thinking they will pay next time, but this never happens. I don't understand why DH just doesn't say lets split the bill but he's not used to people like this- all our other friends just reciprocate.
He says he doesn't want to socialise with them because of this, I can't see why he just doesn't pay for our drinks and let them pay for their own- eg. "shall we split it mate?" instead of paying for everything and feeling offended when the DH says he doesn't want another drink.