I have a number that would qualify for this but I'll start with this one. When I was about 20- a few years ago now(!) - I was asked out by a bloke on my course at Uni. He lived at home and was very old fashioned and I felt sorry for him so always included him when we were going for coffee between lectures etc. Anyway, I was horrified when he asked me but not quick enough to say no or make an excuse. He was delighted, in a 20yrs going on 75yrs kind of way. We arranged to meet outside a cinema in Newcastle- called The Tyneside; art deco, cool films , my sort of thing. When I arrived it was pouring an he was standing outside on grey crimpelene trousers, a red and grey striped tie, a white shirt and a grey V necked buttoned up cardigan like my grandad wore, topped off by a short tight blue kagool with the hood up. He was short and chubby and had a terrible hair cut and wore old fashioned glasses. I saw him from across the road ad contemplated just going home but felt guilty. I thought I would go for a drink or 2 and then leave. I went across and he said we were going to one of his favourite places- not the cinema bar as I had hoped- and wouldn't tell me where. We walked in the pouring rain, me in a blue velvet jacket and jeans, to Eldon Square shopping centre and ended up at the the indoor bowling green where there were about 50 men in their 70s playin carpet bowls. I was stunned into silence. The 'bar' sold soft drinks and we had to sit on white plastic picnic type chairs around the bowling green. He told he often went there and then spent an hour providing a non- stop, mind-numbing running commentary on the games. He didn't seem to notice I wasn't listening. I was desperately trying to think of an excuse to leave. In the end I said, pathetically, that I had to be back at the hall of residence by 9 because my mum was ringing because my grandma was ill. I walked back in the downpour and the blue dye ran out of my velvet jacket and dyed my white shirt. I was wet through. My friends in the hall all thought I was mad for going in the first place but laughed themselves silly when they saw me.
He asked me out at least once a week for the next term. I had split up with my boyfriend and we got back together and this bloke still kept asking me out. One night me and boyfriend were at a party and this bloke turned up. Boyfriend went to loo and I was cornered and told he thought we were meant for each other and I should dump boyfriend. Boyfriend returned and told him to leave me alone or he would flatten him. Took the hint.
I should have just said no in the first place!