You are a cheapskate.

Oh man. We would all gather in advance and collude on not having Bob pay for anything in any clever way we could. We wouldn't be uncomfortable about it. Just clever and firm. We want Bob to be relaxed and let him know we have his back.

Why would they pay for you?

Anonymous wrote:My family would not cover me unless I asked. I would just ask to go to a cheaper place in advance saying you are on a budget and they might offer to pay. They might think its a source of pride for me to pay for myself and losing a job doesn’t mean you suddenly have no money.

this!

you should pay your own way. Surely you have some net worth that didn't disappear. Dont be cheap.

My family would not cover me unless I asked. I would just ask to go to a cheaper place in advance saying you are on a budget and they might offer to pay. They might think its a source of pride for me to pay for myself and losing a job doesn’t mean you suddenly have no money.

My family would 100% cover for me, but I'd have enough emergency savings that I can definitely cover the expenses of my travel.

In DH's family everyone pays their own way. We'd have to speak up about not picking an expensive place to eat.

Anonymous wrote:

Anonymous wrote:Eat alone as then there is no issue.

This.

Loudly announce that you are going to sit alone in your room and eat granola bars and peanut butter you brought from home. Tell the rest of them to enjoy that lobster feed or chateaubriand and not give you another thought.

Hilarious

Be honest about your financial situation and ask them to cover you. Say you'd be happy chipping in for the tip (or whatever) but you're worried About your financial situation. The truth shall set you free. (I speak as someone from a family where no one talked about money freely)

Entirely depends on the situation and the people involved.

Anonymous wrote:Eat alone as then there is no issue.

This.

Loudly announce that you are going to sit alone in your room and eat granola bars and peanut butter you brought from home. Tell the rest of them to enjoy that lobster feed or chateaubriand and not give you another thought.

Eat alone as then there is no issue.

Did you lose your job OP? I would not go on the trip if you don't have enough in savings to cover your expenses. Which, as an adult, you should.

They'd let me pay. Losing a job doesn't mean I'm moneyless. It means I'm taking a break, enjoying family, and getting back to work when I feel like it.
They also know I'd speak up if I didn't have money to spend or would like to borrow.

And were on a pre-planned/sunk cost trip with your parents or well paid adult sibling, would they let you buy them dinner or would they insist on covering you?