<prompt> Human: I want to do the legally correct thing. My understanding is that I should issue him a 1099 for this payment because its over 600...or is that only for small business employeesprivate contracting?EDIT: Seriously, 1,600 is not that much and is completely worth it for the long-term health benefits. Also, I never mentioned how many months this is for...  <response>: The personal trainer should be giving you a receipt or an invoice for the services personal training rendered, and his copy of that receiptinvoice will be his proof of income when he does his taxes. 