Subject: Condolences

My primary boss's cat had to be put to sleep this week, which led to a surprisingly complex workplace etiquette dilemma: clearly, I didn't want to be all business-as-usual, but at the same time, she and I are not what you'd call confidantes, so I didn't want to be intrusive, all, "Hi! It's possible that you would prefer to mourn privately, but I will nonetheless bring up your recent loss in a professional setting! I heard your cat died! That really blows!". I thought a minimally intrusive sympathy card would probably be best, but that would take awhile to get to her (she's out of town), which would leave the business-as-usual e-mail I'd sent 30 minutes before hearing about the cat (but about two hours after the cat actually went) just hanging out there making me look like a callous asshole for several days. Emergency action was required, i.e.:

1. Frantic composition of sympathy e-mail; that the subject line was "Condolences" really tells you everything you need to know about how hilariously awkward and inadequate it was.

2. Hasty excursion in search of a reasonably sympathetic, yet professional card; no reflection on the fantastic Changing Hands Bookstore -- I think the range of available sympathy cards is just uniformly bad -- but it took me about 45 minutes to decide among some really deplorable choices:
a. Outside: Watercolor cat on cloud with halo and wings. Inside: Some kind of tear-jerking sentimental poem about loss. Sure, if my goal was to make her cry more.
b. Outside: Night sky with cat-shaped constellation. Inside: "Heaven is a little bit brighter now". Sweet dancing Christ.
c. Blank card with pen-and-ink drawings of frolicking cats. Relatively inoffensive, but will depiction of happy cats make her feel worse?
d. Blank card with black-and-white photo of sleeping cat. But does sleeping cat have unpleasant visual associations with dead cat?

... and so on. I ended up with a pretty good one with a simple non-cat design and a positive message about having a good life, but it was a tightrope ... a fucking tightrope.