Tax Conversation

[Despite my procrastinating nature, I managed to file my taxes ONE FULL DAY EARLY this year. Nonetheless, the process was not smooth. What follows is an exact transcription of a portion of my evening.]

ME: So, I’ll just take that student loan interest deduction …

TAX-PREP SOFTWARE: Sorry, buddy. You’re not eligible for that.

ME: The hell you say! I’ve taken it for years.

TAX-PREP SOFTWARE: Yes, but you’re married now, so I can’t let you do that anymore.

ME: Say what?

TAX-PREP SOFTWARE: As long as you file a separate return from your spouse, you’re no longer eligible.

ME: …

TAX-PREP SOFTWARE: If you want to file a joint return, I could help you out.

ME: If I file a joint return, my spouse’s income will count towards my loan obligation, won’t it?


ME: And I would pay quite a bit more through increased loan payments than I stand to gain from this tax deduction, right?


ME: Are you smiling?

TAX-PREP SOFTWARE: I am a piece of software. I cannot smile.

ME: But you’re talking …


ME: Is there a whisky-related tax deduction?

TAX-PREP SOFTWARE: You don’t qualify.

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