Dear Jewish Fairy Godmother:

I had lunch last week with the agent who provides insurance to my
firm. I’ve been the risk manager for fifteen years and seen him
through a divorce, substance abuse, car accidents (related to too
much drinking), and other traumas. He’s done the same for me, but I
have never abused anything except caffeine. We’re friends in a
professional way and he has absolutely made me look good at work so
I value him. At lunch he had three glasses of wine, flirted egregiously
with the waitresses, and was generally too loud and bright-eyed. I’m
worried about him. How can I ask if he’s headed for trouble again?

Concerned

 
Dear Concerned:

This is a conversation better had on the phone than by email or
voicemail or even in person. Why? Leave no evidence for anyone else
to read or hear; don’t get trapped in a sticky web of effusive denial.
Your goal is to let him know how he’s acting, and that you care, no
more or less.
Leave a bland message saying you have follow-up from your meeting
last week. Ask when’s a good time to talk for just five minutes. If you
don’t get an answer in two days, call back until you connect. Start and
end with a few sentences that go something like this: We’ve known
one another a long time and seen each other through thick and thin
and I care about you. The middle is: I’m worried about you because
last week I saw symptoms that I also saw during your bad period
before you got clean. You were too loud and too bright-eyed at lunch.
I don’t want to think you’re headed for a slide. You don’t have to
answer me if there’s a problem. But if you are headed for trouble I
want you to know you’re more transparent than you think you are.
And if I am noticing, other people probably are too.
Then listen to what’ll likely be profuse denials. No matter what he
says, just reply with bland platitudes. You’re not going to save him
from himself if he’s careening off the rails. But if there’s a chance to
stop his slide, you’ll have done your part to rescue him.