Cat waking you up in the middle of the night with his singing? Chances are you don't find that very amusing. Rather than screaming at Kitty like a maniac at three in the morning, figure out what he's trying to tell you so you can fix the problem.
Identify the cause of the crying if you can. Could Kitty be lonely? Or maybe he's crying because he's out of food or water. He could also be crying because he can hear other cats outside and he wants to go out -- either to join in the fun or to fight with the intruders. While it might seem that way to you, Kitty is not meowing just to annoy you -- so identify the cause to fix the problem.
Spay or neuter Kitty if you haven't yet. All that crying and meowing could be due to hormones. If you have a girl, she might be pining for boys, and if you have a boy, he could be crying because he wants to go out in search of females.
Let Kitty into the bedroom with you. One of the reasons cats cry at night is because they're lonely. Sure, there's always that chance that he'll keep you up by attacking your toes once he's in the bedroom, but give it a try. Or consider adopting a second Kitty so they can keep each other company.
Make sure Fluffy gets plenty of activity during the day. Cats are nocturnal creatures, but you can help change that -- at least slightly -- by keeping Kitty busy during the day so he can't nap all the daylight away. Get a few toys, play "chase the laser light" or simply wake him up when he tries to take his twentieth nap of the day. By the time you go to bed, he might be just as tired as you and sleep through the night.
- If the nighttime meowing is a recent development, consider taking Kitty to the vet. He might be trying to tell you something.
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