As interesting as that is, it has nothing to do with the law or the IRS guidelines.

http://www.irs.gov/publications/p526/index.html

The only way you could deduct a gift given to a specific person is if it is done under the auspices of an organization. For example, if you participate in Big Brothers/Big Sisters, you can deduct your out-of-pocket expenses for caring for your assigned child.

As wonderful of a thing as it is to donate money to a specific person, you cannot legally deduct it on your taxes.

While I'm sure that many people do deduct whatever they feel like hoping to not get caught or hoping to plead ignorance if they do get caught, that (1) is wrong and (2) isn't an answer to the original question, which presumably was seeking information about what legally could be deducted, not on how best to cheat on your taxes.

Quote Originally Posted by DonHo-kieHi View Post
The deduction is for charitable donations ....which is what you have done. Nuff said.
My take on the "formal charity" is to require organizations who get a large portion
of their funding to prove that they are utilizing the money in a charitable fashion ......protects you as a giver and requires the organization to follow certain guidelines. Small stuff to help someone are certainly "charitable". JMHO