Many toddlers fight bedtime -- often they just want to be where you are. Don't cut his nap to wear him out. Most kids this age still need an afternoon nap. Cutting it can make him cranky or too wired at bedtime because he's overtired.Instead, stick with a consistent, relaxing bedtime routine every night. Give him a comfort object like a blanket or stuffed toy and read him a book. Does he need extra reassurance? Try a night-light or leave the door cracked.

Younger toddlers do mostly play "next to" each other rather than with each other. But don't give up on those play dates. Early play is important. It helps kids learn to make friends. Make play dates toddler-friendly by:
Keeping them short (less than an hour is good)
Keeping them one-on-one
Putting away special toys that might cause battles