Two questions. 1) I am divorced and pay my ex-wife's and children's Health Insurance directly to my ex-wife in the amount of $400 a month. Is there anyway that can be deducted? 2) I have a 23 old son who lives with me. Even though I cannot claim him as

[SeanE1 · Accepted solution]

Unfortunately, the IRS only allows us the ability to deduct the medical expenses, including health insurance that we pay for another person if we can and do claim them as a dependent on our income tax return.  So if we cannot claim someone as a dependent on our income tax return, we cannot deduct any medical expenses that we pay for that person on our income tax return.