I cringe when I think about this one...
My boyfriend had recently started a new job. It was a tradition at his work to have a couple of beers after work on a Friday night, and I was invited to join in.

By the time I arrived, it was just my boyfriend and one of the younger ladies left. She asked how we had met, and I explained that we had met over ICQ (of all things). We had to explain what it was and the whole business of talking to strangers over the internet. This should have clued me in to the fact that she was not the most internet savvy person, but sadly I was oblivious...

In the course of the discussion she ended up asking him, "do you talk to many people over the internet?". Mistaking her shy tone for a certain measure of cheekiness and familiarity, I replied, "Yes, he has certainly seen his fair share of boobs over the internet!" She made an incredibly awkward reply and my boyfriend shot me a murderous look. Not content with this, I followed up with, "Haha, he's kicking my leg now to tell me to shut up!".

I don't think he's ever going to forgive me for it.

P.S. I work in HR and really should know better than to engage in saucy conversations with people I barely know, let alone people with whom there is a working relationship.
(ridethefader, Sun 6 Nov 2011, 8:57, Reply)