Lets pretend this current dilemma exists with "Getbigger X:"
Getbigger X is a multimillionaire. Getbigger X has a girlfriend. Getbiggers X's girlfriend also has a sister who has a boyfriend. Sister's boyfriend does not make a lot of money.
Getbigger X is going out for Fathers day with the following people:
Girlfriend
Sister
Sister's boyfriend
Girlfriends mother and father
Getbigger X, the multimillionaire, wants to pay for the whole Father's Day Dinner (even though Getbigger's X girlfriend wants to pay for it, but Getbigger X will not allow this). However, Getbigger X is hesitant to pay for the meal in front of everyone, in an effort to avoiding making the sister's boyfriend feel bad, who cannot afford to "chip in" for the meal.
What should Getbigger X do? Have the girlfriend pay for it, then give her the money on the side?