Just as Afinkawan did in this thread, here is my little effort which I submitted to the one page play contest
TEN DOWN NINE LETTERS by Mikey Jackson
HUSBAND:
I'm stuck on this one, dear. Ten down. Nine letters. The fifth letter is an S.
WIFE:
(WEARILY) And what's the clue this time?
HUSBAND:
An unhealthy follower.
WIFE:
An unhealthy follower? Um. A fat fan?
HUSBAND:
Don't be so absurd. Not enough letters. And, like I said, it's got to have an S in it.
WIFE:
I'm only trying to help. It's the crossword's fault. It shouldn't be so cryptic.
HUSBAND:
It's supposed to be cryptic. That's the whole point.
WIFE:
Oh, darling. I'm tired of this now.
HUSBAND:
But we could win a thousand pounds.
WIFE:
Oh, you and your competitions. Every contest you see, you have to enter it.
HUSBAND:
You've got to be in it to win it.
WIFE:
But you never win anything.
HUSBAND:
We won that year's supply of baked beans once.
WIFE:
Yes and we're still trying to get through them.
HUSBAND:
And we could win that cruise. You never know.
WIFE:
I don't think the sentence "I'd like to visit the Caribbean because I love entering competitions" stands much of a chance of winning, do you?
HUSBAND:
Oh, come on. Help me out here. Nine letters. An unhealthy follower.
WIFE:I can't dear. I've got to make our beans on toast. Oh, I don't know. This unhealthy obsession of yours...
HUSBAND:
Aha! That's it! Nine letters. An unhealthy follower. Unhealthy obsession. Obsession. Thank you, dear. I don't know what I'd do without you.