<prompt> Human: I mean hey, why not - its the internet! I have a friend who helped me out big time at work and Id like to give him a gift of 1000 from my small business. Can a business gift money like that or will I have to give him a 1099 since its over 600? Nothing worse than a gift that comes with a tax form later in the year. Well the only thing worse is getting a huge tax bill because the IRS doesnt like my way of saying thank you.  <response>: The rules of UnderhandCloak-and-Dagger dealings state quite clearly that an under the table transaction doesnt actually have to have a table involved, but the money DOES have to be contained within a brown envelope or briefcase for larger amounts 