DS is very sociable. He has been in nursery full time since he was 2 year old. He has never had any reported problems socialising but there has never been a special friend. He is an only child. Cousins live far away. We occasionally see some friends with children but most week-ends and holidays are spent within the family i.e. mum and dad. When we go to the park DS tries to play with other children. He is not clingy or shy. He goes out there and tries his luck. Inevitably he is not always successful especially when he "targets" older children. Until now I have avoided offering help or tips on how to make friends thinking that it would be best if he worked it out himself. After today I am starting to think that I may be expecting too much from a 4.5 yrs old. Today we went to the park, my son approached some children who looked a bit older than him. They all run around together for a bit but then the other children went off to do other things. DS and I played together for a while and then he saw one of the boys he had been playing with and went off again. I heard him saying "hello I am the same boy you had been playing with before" which did not cut any ice with the other boy. I tried to suggest that the other boy may prefer to play on his own but DS would not hear of it. I went up to him again after a good 10 minutes of watching him following this boy around. He broke out in tears and I felt terrible. Clearly he could not understand why the boy did not want to play with him any longer and that following him around was not going to help. On other occasions I had seen him going out of his way to try and please some older children with very scarce results. I know I need to say something to him and I did sort of start tonight before bedtime, but it did not sound too convincing even to me! Help please!! Thanks