Well I had a fairly uncomfortable one, although nowadays it's just humorous.
Anyways a little back-story:
So it was when I was in 7th or 8th grade I believe, around 15 years old. We had a week when you went spent a week working at a real job, to feel what it's like or something. Anyways, I was at a restaurant which was like an half hour bus ride away. Not too bad, but I had a friend that lived just next to it, he was maybe 21 at the time, living in his own place.
So I tried to argue (that is nag, nag and nag) to stay at his place cause it would be easier and I could sleep longer, but they would have none of it "school day's aren't sleepover days", they pretty much just said no on principle.
So I don't stay there and that week I fall asleep with my computer on, and MSN messenger running. So my friend sometimes has a special kind of humour, I'm woken up by my father who is pointing at the screen and asking: "What the fuck is that?" My friend had written to me: "If you don't watch out, I'll break up with your dad!"
So this isn't too harsh, but my dad has noo reservation for gay jokes at all. He instantly believes that this guy is 100% super gay and has corrupted me and that my nagging to sleep at his place was for whole other reasons that to just be close to work. So I'm forbidden from ever seeing him again, asks me how you can even say something like that etc. etc. I try to explain to him that it's his kind of humour and that it's just a joke, but dad can't fathom it.
But after a couple of weeks it has cooled down a bit and I'm going up to him to play some D&D, something we did once or twice every couple of weeks. Anyways, I'm standing at the station waiting for the train to go up there and my dad calls me and says: (and this is the real price winning conversation)
Dad - "So, I'm not sure I want to let you go up there!"
Me - "Dad, I've told you a million times! It was a joke okay?"
Dad - "Ok, but if I find out in a couple of years that you've had some kind of fucking gay club up there, I'm removing you from my will. Ok?"
#Click#
Suffice to say my only thought was "WHAT?"