Can I file a 1099-MISC if I paid them under $600?

Hello, I have been looking for an answer to this and haven't found one.

 

If I pay a contractor of mine, for example, $300 in a year, and they request that I file a 1099-MISC for them, can I? I know I'm not required to, as it is under $600, but if I receive a request from them, is there anything wrong with filing one?

 

Thanks in advance.