Dear Jewish Fairy Godmother:

My husband and I had a rocky divorce. The boys stayed with me until
each turned 16, then fled to their dad’s. The eldest, Aaron, is now a
college sophomore and our relationship has improved immeasurably,
so much so that I invited him to spend spring break with me in Costa
Rica. I was looking forward to a week of bonding time, and a chance to
reestablish the closeness that I had and would like again. He asked me
if he could invite along his girlfriend of five months. Other than my
disappointment about not having one-on- one time with him, I am
cautious because this girl (who seems nice but who can tell much from
a meetings at restaurants) is still a high-school senior. Senior, as in,
under 18. I don’t want to disappoint him, don’t want him to back out
of the trip, and don’t want to set up a situation where things are worse
after the trip than before. What say you?

In the Crosshairs

 
Dear In the Crosshairs:

You’ll need to thread this needle very carefully. While I understand you
have high hopes for your renewed relationship with Aaron, you’re still
the parent. If he withdraws again, know that he’ll come back again.
It doesn’t sound like you know this girl’s parents at all. That where I’d
start. Ask for their contact info and interact with them directly. Explain
the trip’s location, logistics, accommodations (including proposed
sleeping arrangements), and costs. Ask them explicitly if their
daughter has permission to go, and assuming you’re not footing the
bill for her, if they’re willing to pay for her part of the trip. Tell them
that you would like them to negotiate agreements with their daughter
about behavior, and then get a copy of the agreement, as well as a
written release from them about your personal liability if anything
happens on the trip. Get a copy of her medical/insurance info. Check
with the airlines to see if there’s anything else you would need being
the adult traveling with a minor who is not your own child and with
whom you do not have a legal relationship. If you’re lucky, someone
external will intervene and you’ll look like the good mom. If not, be
prepared to have a very different vacation than you were planning,
with lots of chaperoning.
PS – an alternative is to say, not this trip, but once she’s 18 we can
all go for a weekend together. The odds are only 50/50 they’ll still be
dating.