Yes, tax season can have some pretty funny moments. After nearly 30 years of the annual ritual, I've seen a few funny moments.
One woman, a prospective new client, came in one year. She was part of a traveling musical group and the show involved some nudity. She wanted to know if her breast implants could be claimed on her tax return. I told her that I'd have to do a little research on the matter but asked her a couple of things to consider. 1) What portion would she consider to be of a personal nature and how much would be for "business use." 2) since some expenditures are considered to benefit more than a single fiscal year and would therefore be claimed over a number of years, what was the expected lifespan of said implants. After a fairly lengthy discussion she ( and her implants ) left, never to be seen again.
A woman came in one year with the tax slips for her and her husband. Hers was pretty straight forward - T4's, RRSP, etc. Her husband was a cabbie and had a fist full of T4 slips. I asked about his tips for the year. She thought about it for about half a second, looked me straight in the eye and said "my husband doesn't get tips, he's an asshole ! "
One woman told me how much of a tax refund she wanted for that year and would appreciate it if I would prepare the return accordingly.
Most of my career was pretty serious stuff but there was always a chuckle just around the next corner.