Whaddya' do?

I have a parenting issue on my hands that has me completely stumped. You'd think after 24 years and 4 kids, I'd have most of the answers, but not this one apparently.

My older three are amazingly independent creatures. They are all eager to try new things, meet new people, go new places, etc. And then there is my youngest. Brilliant guy. I mean, SMART. So smart in fact, that as we have been going though this issue, he went and got a book (Overcoming Anxiety for Dummies), read the whole thing and then proceeded to inform me that he had a "classic case of separation anxiety disorder". He's right--he does.

Four years ago, when he was about 8, he didn't have much trouble with my leaving now and then. I was out on book tours then, plus several companies I work with flew me to their headquarters for special training/projects. Although he missed me, he was fine with it.

Now, I am trying to go away for three days and two nights with Nicole and the boy is in tears every day over it. He has gotten progressively worse over time, refusing to spend the night anywhere and hating it if I go away overnight. In January, I had to leave for 6 days to go to Indiana and be with my mom and he really had a melt down. He begged me to not go or take me with him and the emotional pain of going through that was almost as awful as losing my mom. I had hoped that trip would help him--he'd find out that he was really ok without me and coped fine--which he did--but it hasn't helped at all. In fact, I think it's worse.

I tried talking to him about it last night and he did mention that he was somewhat worried about me when I was gone, even quoting statistics on how often people have car accidents, but we both came to the conclusion that fear for me was not the cause of his anxiety. He says, "I know my subconcious mind knows why I feel this way but my concious mind doesn't have a clue". See, smart!

I have wondered if death is bothering him more than he lets on. In the last 6 years, he has seen one of his favorite homeschooling moms die unexpectedly, my dad died, my mom died, and my sister in law died. (Heck, I think death is bothering me too, at this point). He doesn't seem to have any preoccupation with death and never asks me about it . . . although we generally avoid him watching any movies where something bad happens to the mom.

So anyway, the weekend is approaching and I am worried about it. I don't want to walk out if he is sobbing and asking me to stay. I also don't want to cancel my plans and miss this opportunity with Nicole. I am so torn. I've thought about finding a counselor for him, but it has to be someone who won't go the "Buck up and be a man!" route or "If you hadn't homeschooled him. . . " route.

I love this boy so much and to cause him pain hurts me. I just don't know what the answer is or the best way to respond to his feelings. Any experts out there? Any ideas? Any suggestions? Any anecdotes? I'm lost here. I want to help him and I don't know what to do!