alison.... i think you just need to open your mouth. my impression from here is that you are a bright woman with good ideas. yes you have an issue with confidence, but sometimes the best solution is to pretend to be confident, you may find you start to believe i
whats the worst that could have happened? you come out with the brilliantly dorky 'i like your bike' and he either thinks you're a wierdo for liking his old pub bike ( unlikely) or he is pleasantly pleased to bump into someone with a similar llove for old junk and you have a nice 5 minute chat and someone to pass the time with next time you pick up the boy.
if we all made the effort to start a conversation the world would be a better place.