Dear Jewish Fairy Godmother:
I just had a deeply personal and deeply disturbing conversation with
the person I have been dating. He misunderstood something I said,
brooded on it for a week, and called prepared to end the relationship if
it “isn’t good for you and more.” I love this guy though there are
certainly reasons that it might not work. How do I find the lines
between honesty, self-protection, keeping the relationship going,
making him know what I need, not undercutting myself?

Dear Hurting:
You need to be as honest as you can, with yourself and with him. That
also goes for what you say to your closest friend(s) and your
counselor, which, if you do not have, I am going to recommend that
you consider finding. There is no easy, single, sweet spot to balance all
the concerns you have named. Relationships are also a very dynamic
equilibrium. That means what’s chocolate for it one day might be rat
poison the next. But if you cannot be generally honest about what you
are feeling, or if you cannot express yourself, feel heard, and feel that
your fellow cares about your feelings in the way you want him to, this
may not be a good long-run fit.

You do need to ask yourself the tough Valentine’s question: is he
trying to tell me he wants out of this, and looking for a non-hurtful
way to say it? That’s a hard question to ask. And you shouldn’t do so
unless you’re prepared to hear either a Yes or a No. My advice is to be
true to your own heart, and hope he hears you and responds the way
you want him to.