For my birthday, my mother-in-law bought me tickets to see the musical Wicked. It was amazing, and I highly recommend it. She was supposed to be our babysitter for the event, but the hurricane kept her away, and we had to find someone else. We asked a newly married couple in our ward that know our kids (he's happy to quietly play with them at church), because we knew we'd be out pretty late, and it was a school night. The kids were very excited to have babysitters, and were thrilled to have someone new to tell all their stories too.
They played with them for a bit, then put them to bed. We had put their jammies on, and told the couple that when it was time, they should read them some stories, then put them in their beds. I told them that I assumed Kiddo would just go to her bed and put herself to sleep. I also said that Babs might be a bit harder. I suggested they could just put her in her crib, and close the door and let herself cry it out. But, I am quick to assure babysitters that they are the ones with my kids, so they should do whatever they can live with.
Babs tried multiple ploys to not go to bed. She informed them that her mommy wanted her to be up. She asked for a bandaid. She tried every excuse she could think of. They tag-teamed rocking her, and trying to get her to peacefully go down.
Which she eventually did, because she was asleep when we got home.
Our friends are good people.