How do you hit on someone at work?

This is complicated enough when you're a guy hitting on a girl. It's very complicated when you're a closet bi guy hitting on a guy.

It's even more complicated when the "work" is a client organisation.

Anyway. Very attractive guy is a contractor at my client.

So after a while I came up with a brainwave: how about a polite anonymous email?

Of course this could still all go horribly wrong. He could see the anonymity as cowardly. He could play along and then expose me. Or he could be scared and think this is someone playing a practical joke on him.

Or he could just be straight.

Sadly, he and I were both on leave this week. So I got the "XXX is out of the office..."

Let's freaking hope he did not set his work mail to auto-forward to a colleague...