Wife wants to pay for her 35 yr. old sons trip to Alaska.. He quit his job to do theatre. I said No?

Excuse me!!!! WOW!! It is ok to pay for the sons that the two of you share but not the one SHE has from a previous marriage (that is not yours)???? If I were her, I would pay for all of MY sons and you could just put on a smile and deal with it or stay at home. The bottom line that you are missing is that your wife WANTS to pay for her son and she WANTS all three of HER boys there on this FAMILY trip! Geez!!

If your wife has monies separate from yours or what you both have jointly...then let her waste her money. If she expects this to come out of mutual funds...then no. He's a big boy. He pays his own way or his Significant Other does. That is, if the two younger boys are MINORS...if they are adults and supporting themselves, then all three pay their way. period.

Well, at 35 the man is an adult.. i suppose this is a decision you and your wife need to make together.

Somehow, it seems that, if we invite a person to take a trip with us, we ought to foot the bill.

You are right. The last thing you want to do is enable him. Somehow he needs to learn that he has to WORK if he wants to be able to take vacations and do other things that require money.

If it is a family trip then you should consider floating him a "loan" with the realization that it might just not ever be paid back. The price of that ticket might just be worth the avoidance of marital headaches and drama with your wife.