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Tax Q&A: Can a Bad Date Ever Be Deducted as a Charitable Donation on Your Tax Return?

April 15th is right around the corner so I want to take the time to answer a question that a lot of women have, one that the IRS website simply doesn’t address:  Can a bad date ever be deducted as a charitable donation on your tax return?

It probably seems like the answer should be an unequivocal “yes” when you recall some of the dates you went on last year that felt more like extraordinary acts of altruism than the beginning of romance. 

You might be thinking “I tried to teach that guy basic social skills out of the kindness of my heart!  Doesn’t that count for something?” or “I kept that scary dude off the market for six weeks while I dated him.  Isn’t that sort of like law enforcement?” 

It seems like women often have to step in and help out where a man’s parents have failed him, the educational system has failed him, or worse yet, psychiatry has failed him.  But unfortunately, despite all of these acts of giving that we do each year, most men do not qualify for the 501(c)(3) status that would make them a tax-exempt charity.  So, the time we spend dealing with them is not deductible. 

Someday, when more women work for the IRS, I fully expect this rule to change.