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[quote=Anonymous][quote=Anonymous]I personally would be glad about the fostering friendship between the kids because my kid doesn’t have the easiest time making friends. Can you reinforce the end time and express that she will have to take extra care when she sets up play dates like this? (And to be clear it is still a play date even without the other mom.)[/quote]

OP here.  Normally, I would be glad about fostering friendships, but DD and this girl get along just so-so.  They tend to fight a lot and DD got really upset after their last play date - talked about how sad it made her for weeks after, something she NEVER does - and said she didn't want to see this girl anymore.  Babysitter was on this last play date and others so is aware of this.  She is a kind, generous person and I think her impulse to offer the play date had more to do with her wanting to help the other mom and less to do with helping DD make friends.  As I'm writing this, I'm realizing that if sitter had offered a play date with one of DD's other classmates, I wouldn't be half as bothered.

Reinforcing end time is a great suggestion and I will do that.  I am also going to ask her to run play dates by me in the future because of what I described above and because there might be considerations such as schedule that she is not aware of.

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