Can I deduct medical expenses that I paid for my girlfriend's medical bills? She has about $1000 a month of medical bills (prescriptions etc) and is in between insurance. I've been covering it for the past couple months. Is that deductible on my taxes? Or can she claim it as a loan and deduct them on hers?
It's not deductible on your taxes unless you can claim her as a dependent according to this definition, and then only if it's more than 7.5% of your AGI.
Unless you consciously drew something up as a loan prior to paying for the medical expenses, I think she'd have a hard time convincing an auditor that she paid for them. Even more so if they're your checks.