Thats a question for the professional man - YOUR CPA!
I dont trust H&R Block people......sorry! I have a CPA do my taxes. Call them up , ask for their fee and do it!

Not unless you are in the weight loss business and your loss is part of an advertising campaign. Even then it would be questioned.

A weight loss program that is treatment for a specific disease or diseases including obesity that are diagnosed by a physician are deductable.
Christine EA Master Tax Adviser
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This advice was prepared based on our understanding of the tax law in effect at the time it was written as sit applies to the facts that you have provided. http://www.hrblock.com/taxes/tax_tips/in...
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Yes. Weight loss programs as specified in IRS publication 502 qualify as a medical deduction on schedule A.
Richard K
Master tax Advisor
HR Block
This advice was based upon my understanding the law in effect at the time it was written as it applies to the facts provided by you. See my profile for more infromation.

Only if your doctor specifically ordered the program as a medical necessity, and it really was, and the IRS recognizes the program as a valid deduction and you are able to document all of the above.
Otherwise...prolly not.