I'm going to go against the grain here a bit. I think it depends. We live close to the city (about 12 mins to Flinders Street on the train) so for us the city seems pretty local. My DP was completely comfortable about SD (who was 13 at the time) going to the city with friends - during the day for shopping. Would have been a totally different story at night.
He did cop a bit of flack from SIL about letting her go on the train without an adult but he was confident that a) trains aren't that dangerous and he should know, he's a train driver and b) that she was going to do what she said she was going to do ie. shop.
So for us, the city is not much different to her going anywhere else unaccompanied during the day because it's close. We might feel differently if it was a big trip and if we weren't sure that she had enough street smarts to not put herself in dangerous situations.
But it also depends on how comfortable you feel with the whole idea. We were, BUT that doesn't mean that you should be and I'm not saying let her go.
I don't like the chaperone idea. I would have HATED it and I think you either trust her or you don't. But I do like the idea of gradually working up to it and establishing groundrules about contact while she's out. Break the rules and it's off the agenda. I think that's fair.
Or you could always do what my DP's parents did. He was a geeky trainspotter who used to go to the city when he was 14 and photograph trains from the Spencer Street bridge every Friday night and this was WAY before mobile phones were around. Anyhow, they got a little concerned that maybe they were being too trusting so one night they let him go as usual then jumped in the car and went to Spencer Street to check. There he was in his anorak photographing trains like he said he would be. They didn't tell him that story till years later!





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