When I was 15, I asked out the most terminally shy Guns n Roses fan in Luton. I thought it was going to be ace having a rock n roll girlfriend, but our one and only date was depressing, we were obviously underage so I had to take her to an Irish social club my parents occasionally went to - at 5PM - because I knew the bar staff wouldn't throw me out. I tried to defuse the weird silences by taking the piss out of the old blokes at the bar, but she just seemed to get more uncomfortable and couldn't stop blushing, and her voice went really squeaky. I had a half of cider, she had a coke, then an hour later I made up some shit lie about having to go home, and we never saw each other again. Apparently she's a successful entrepreneur now.
Apart from that, taking a Norwegian girl to a Millwall match in my 20s was, er, 'fun'.