In and Out Revisited

"You're so in, and I'm so out!"

Aggie's brilliant In and Out posts reminded me of something a boy wrote in my year book ages ago.

Dear Woodsy,

When you're in, we're out.

See 'ya around,

(signed) Tall, Brawny Guy

For years I have been perplexed by what he meant. Was he being crude? Or, was he being dismissive? Maybe he saying I was cool and he was passé.

What do you think he meant?