I have two cats & we had to keep then apart for about a week when we adopted the 2nd. (just to make sure he didn't have anything he could pass to her) He would cry everynight when it was bed time. He'd cry until I got up & laid in the room w/ him for a hour or so. After that week we keep both of them in our room @ night. If you have time I would play for @least 30 minutes w/ them before it's time to go to sleep. On my husbands nightstand you'll find a basket w/ Bernie in it & on my side you'll find a kitty bed w/ Squeak in it. They both put themselves to bed now when we turn out the tv. Cat's are such creatures of habbits I even catch Bernie sometimes during the day taking a little nap in his bed I should add the food/water & litter box is in our room.