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World's Worsest
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Start with World's Worst Chat Up Lines, till it wears out then start a new topic.
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Ahem... Aren't those Miss Pendergrast's pantyhose lying in a heap under your desk? She does go beyond the call of secretarial duty, doen't she?
We're practically family for I've been having a liaison with your wife. But that's not the half of it, your daughter is 7 weeks pregnant.
Badges? We don't need your stinking badges!
Of course I've been taking off early most days at 4PM. I didn't realise until just now that when you hired me you said there was a compulsory "forty hours a week" policy that employees must abide by, I mistook it for a "four tea hours a week" mandate.
I know I came in late, but I'll leave early to make up for it.
Oh, when the application form asked for any previous criminal convictions, I thought it only meant in this country.
"Have you ever danced with the Devil in the pale moonlight?"
Time for another topic, I think

World's Worst Thing To Say To Your Child's Teacher
He's very advanced, you know - he knows how to use Log Tables.
No I haven't taught him to walk or talk, that's your job!
We don't believe in constraint or restricting his natural creativity. So for the last four years he's been running wild in the garden, learning from nature.
(To a kindergarten teacher:) Are your lessons intellectually rigorous?
Forgive me, I've heard it's true my child has to share a class with those of inferior races. This surely isn't true?
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