Dear Jewish Fairy Godmother:
I’ve been in relationship with Malcolm for three years. He’s twelve
years older, has two boys, and used to be employed and self-
supporting, got involved in a stupid venture, lost his shirt, had a rough
patch when I started supporting him, and is now on his way back to
solvency. I’ve paid for rent, food, and even part of his child support for
the last two years. A friend of his gave him, repeat gave him, four
tickets to the college championship game for his birthday, saying you
haven’t had any fun for a long time. It will still cost a fortune I don’t
have to get us there and back, put us up and feed us, not to mention
souvenirs etc for the kids. I just want to give them back. He wants to
sell them, or maybe sell two to pay for a trip for just the two of us (the
kids would stay with his ex). I’d love a vacation but I still think we
can’t afford it. I’m also not sure I want to keep supporting him, but
that’s a bigger problem.
To Go or Not to Go?

 
Dear To Go or Not to Go:
I agree that the prospective vacation is probably the least of your
problems. I also happily note that your email is not littered with the
usual I love him so much that generally peppers emails from people in
troubled relationships. That’s how they justify any number of
egregious lifestyles, supporting someone you’re not married to for
several years among them, though not the worst.

 
A vacation is a bad choice for this time of your relationship and
finances. I don’t think you get to sell the tickets and pocket the
proceeds. I think you owe it to the donor to tell him you will not use
the tickets. Ask him if we wants two or four of them back. Or offer to
sell them for him, and ask for some share of the proceeds as a thank
you for doing the work. If you’re really lucky he’ll tell you to keep the
tickets and the money from selling them. But to just act as though
you’re going and then keep the cash seems rude. It also should give
you another window to look at your boyfriend’s values.