We've very rarely had a babysitter for when LO (28 months) was awake. DH and i want to get into the habit of leaving her with a regular sitter a couple of times a month. We have an event to attend next month that will require the babysitter to put her to bed.

I don't necessarily want the babysitter to put her to bed the first time she meets LO. I figure a 2 hour trial run would be good. What would be the best time of day?