Q: My 5-year-old begged me to sign him up for soccer, but he broke into tears as we left for practice across the street. I told him, “Let’s just go and watch,” but he remained weepy and clingy, saying he was scared. After 40 minutes of watching other kids while he complained about being there, we left. He plays well and makes friends at school, but this has happened for every extracurricular activity we’ve tried. I’m feeling frustrated and unsure how to respond.
That sounds like a very difficult and upsetting situation for both of you!
The good news is that you've recognized a pattern: your son gets scared when he enters new activities. It's always easier to make a plan when we have an idea of what to expect. Your idea of having him watch first before trying seems like it will be helpful. The problem was probably he was already too worked up to embrace your very sensible suggestion! It's a good sign that he plays well with friends at school.
You have a choice now: