Dear Jewish Fairy Godmother:

How do you suggest dealing with a significant inequity in
income in a dating situation? We are both middle-aged and
started out life with a similar middle-class trajectory: stable
home, college, even both taught (me math, her English)
though not on tenure track. Then I went into business and
made a good living after risking a significant part of my then
life savings in a tech firm that did well. I’m not a millionaire
but I have a nice home and can regularly eat in restaurants,
go to theatre, etc. But my love life was not successful and I
divorced twice, both non-acrimonious and each ex happily
remarried.

Now I have met a woman I think I could very
much enjoy. But she is poor as a proverbial church mouse.
She says she lost everything in the recession, but there are
big holes in the story she told me. I haven’t pressed. I don’t
mind treating her when we go out (my generational
training). But I am reluctant to set up a pattern of paying for
everything to keep her life afloat, though it is clear that she
would be less stressed with an infusion of cash. I don’t think
I am ready for marriage, but I she’s the most fascinating
person I have met in a decade. Is there a middle path I can
walk for a while?

Not Miser

 
Dear Not Miser:

You don’t say how long you have been dating, but short of
an actual proposal, engagement, and wedding, I’m cautious
about suggesting you undertake large financial
entanglements. Many people suffered in the recession and
lost a lot. Teachers were probably already more vulnerable
on the financial food chain. But you cannot rescue them all.
Financial inequity in a relationship almost always becomes a
source of stress between couples, dating and even married.
Some work it out with various cost-sharing plans. Others
ignore it. But biting your tongue now is not a good recipe for
a long term balance.

 
I would do two things. First have a serious conversation with
her about money. Say you’re concerned by her past but
want to hear her history and really understand. Then say
when you go out on a date you are happy to pick up the tab.
That means meals, tickets, and various treats. But that you
are drawing the line on actually lending money. If that’s a
deal breaker, she will search for a more generous date and
you will lose her. Only you will know if that is a bigger loss
than money.