We're having a group holiday, eleven of us. Just a few days to do a shared interest activity. A very laid back group, most have been away together before but there are a couple of newcomers this time. Arrangements are very relaxed and easy. Everyone books their own flights, a couple of people will offer to drive to the airport and we'll share the cost of parking. Then someone volunteers to organise an AirBnB.
This time I'm doing the accommodation. Suitable place has been found and all agreed. I've said I have no time this week unless it's done today, but I'm happy if someone else want to do it. Because there are a couple of people in the group without a track record for these things and because it's a lot of money, I've said I need payment before booking. c. £150 each. I've had 9/11 payments, plus mine today, just one left.
The missing one is a man who hasn't travelled with us before but we know well. He's ultra reliable and not tight with his cash - first to offer to buy the coffees etc, thoroughly decent all round but he lives an unconventional life, left school at 14, works as and when as a labourer. He's already booked his flights and the event we're going to. If he's tight for the money I'd lend it to him, I'd treat him if need be, he's done me loads of favours (I'm sure it won't be) but how do I go about offering without offending him?
I wasn't prepared to advance 10 x £150, but £150 isn't the end of the world for me, if it helps someone out and means I can get the booking done.