Going back a few years, in the location I previously worked there was a Pret-a-Manger. I'd usually nip in once a day for a snack mid-shift. One day I walked in for breakfast, place deserted, with a beautiful girl behind the counter. Early twenties, petite, great hair, piercings - exactly my type, hadn't seen her before. Struck up a conversation and got good vibes. I left to eat my breakfast in the company staff room and decided I'd have to head back and chance my arm - rare for me, I'm not that direct and prefer to play it quietly. En route to the coffee shop I had to pass one of my company's branches. Colleagues called me over and I made the dire mistake of telling them what I was up to. This was about ten metres from the coffee shop and the object of my affections was outside by herself at this point, clearly on her break.
As I walked over to her, I could feel the eyes of my colleagues burning into the back of my head as they were practically straining their necks to watch the show. Totally threw me off, I walked up, chatted some **** and then compounded it by swearing (not at her). She clearly thought I was a great catch

. Safe to say it didn't go any further, and to make matters worse she was a family member of the partner of the girl I frequently worked with - she'd often come over to my workplace to chat to my colleague as I sat there, mute, quietly hoping for a sudden sinkhole to envelop me.
Another one, back in 2006 I was on a year's trip around Australia. To set the scene, partway into the holiday and myself and partner had just finished a 3k mile self-drive from Cairns to Darwin in three days. Decided to take a break at this point and signed up for a guided group adventure down to Alice Springs. There were 9-10 of us, all early twenties except for an Irish lady perhaps twenty years older, named Hilary. To be charitable, she 'wasn't my type'. Nor was she anyone else's type as she was a bit of an oddball and most people shunned her. But I can't be like that with people and as the days passed we got into conversations. One day we had a free afternoon and the option to do whatever. So myself and partner decide to kayak the Katherine Gorge. Sitting in the kayak enjoying the blazing sun, beautiful scenery - life is good. Then a tour boat approaches. I pay no attention to it until I hear: "Cooooo-eee, woooooo-ee. ANDY. RAAAAAANDY AAAAAANDY". I look up startled, and it's Hilary at the front of the boat, standing up, shouting, waving furiously, with the entirety of the boat now looking in my direction and snapping away. Safe to say she had never been the object of my affections and I'd have quite happily the boat capsized and her dragged off by a stray croc. Nor was there much conversation between us for the remainder of the trip!
Another one, more funny than embarrassing. I part-organise a yearly seminar. Last year's event is going well, no dramas and it's getting towards afternoon refreshments. In my usual location at the back of the room avoiding as much contact as possible, I am first out and into the catering room. I ask the barista for a tea and then engage in conversation with one of the tutors. I am too engrossed in the discussion and as the barista hands over the cup, I do some sort of open hand gesture and it falls straight through my hand, right as a bunch of other professional tutors wander in to see the cup hit the floor, leaving it awash with Earl Grey.
Finally, a couple of recent ones, cringes for someone else:
My son is 18 months old, goes to a local nursery. We have had an occasionally frosty relationship with said nursery as they come across quite disorganised. Fast forward to a recent parents evening and they are clearly keen to impress. They keep a picture book for each child, with the activities they have been involved with. So the head of the nursery is proudly showing us our son's logbook until we get to a few pics which aren't our child. No biggie, but the staff member is clearly embarrassed. Keen to make amends she then flips to a "gorgeous picture at the pack, you'll love this one". Nope, that's not our son either. I have never seen anyone turn so red...
Lastly, I have an acquaintance who works in the media. Not a friend or colleague, just someone I know in passing through my employer. He asked his company for time off, didn't specify why. Rejected. It was for a job interview, so the guy calls in sick and attends the interview. His prospective employer had no real affiliation with his current employer; same industry, but no links. It was a panel interview and he turned up to find his boss sitting on the panel....
He didn't get the job and was fired shortly after. In a double case of karma, before he left he defaced his company's website. He now needs a reference from said company to be able to supply certain details to my employer to be able to potentially progress his career.
