Last night was Evan's first evening with the new babysitter, and it went well. I guess we'll know how well, the next time I check her availabilty! She played with him, fed him dinner, and even put him to bed. We were gone five hours and it was great! We went the standard "dinner and a movie" route and stayed close by just in case. I was leery of bedtime, but she said he only put up a small fight (lucky!)
The babysitter is sixteen and really sweet, plus she's got a lot of experience taking care of her younger siblings, so I felt confident that she'd do a good job. I was completely new to babysitter etiquette, though. Do you leave them dinner? When do you give them their money? How much do they need to know? With friends and family you don't have to worry about etiquette. But, I think we figured it out, and now we're good to go for next time.
We were preparing Evan all day for her to get there and he was so excited. I could tell he must have had a good time, because the first words out of his mouth this morning were to ask where she was. Apparently we won't be the only ones looking forward to next month's date night!