It happens to the best of us: you get bored of filing the same W2s year after year. You want a break from your nagging tax burden and dip a toe in the waters of tax infidelity. Next thing you know, BOOM, you’re trying to balance your old books and a sexier, completely illicit book at the same time. Eventually, you get sloppy and the IRS finds whiteout all over your 1040.


It may feel like life’s over, but don’t give up so easily. In many cases, American citizens and the IRS can come out the other side of a cheating scandal with a healthier, more sustainable relationship. There are plenty of ways to show contrition for your acts, prove to the IRS that it was a one-time mistake, and avoid bringing in the lawyers to move along audit proceedings.

  • Start a clean slate by revealing all previous tax infidelities. This includes offenses such as writing off Jet Skis as a business transport deductible because technically you could get to your office via a complex network of urban canals.
  • Make a thoughtful gesture for the IRS. Consider sending flowers or writing a romantic letter in which you report any suspicious cash-only dry cleaning businesses in your area.
  • Show the IRS that you don’t want to end things with an audit. Agree to start seeing a therapist an effort to better understand why you cheated as part of a reasonable plea bargain with a local judge.
  • Remind the IRS of simpler tax days. Create an apology collage out of all the old receipts you filed when you first entered the workforce.
  • Do something drastic. Why not stand outside of IRS headquarters for 24 hours with a boom box blasting Peter Gabriel’s “In Your Eyes?” You know for a fact the IRS loves Say Anything references.
  • Reestablish healthy communication channels. Check in with tax officials every few hours by calling or texting and declaring any recent income or 501(c)(3) charitable donations since you last talked.
  • Be open to change. There are tons of ways to get the job done besides Turbo Tax. If you’ve thought about spicing things up, experiment with new loopholes in the ever-changing tax code or consider getting an accountant involved as early as January.
  • Let them know you’re thinking about taxes all year round. Even if it’s not tax day season, send a cute homemade gift to IRS headquarters in Washington like a personalized “IOU” for $12,000 in back taxes.
  • Prove you’re serious and rededicate yourself to honest tax filing by listing all 80,000 IRS employees as dependents.
  • Plan a surprise, last-minute tropical vacation to the secluded Cayman Island or Swiss Alps. Be careful not to mention how you learned so much about the exotic areas because of your trips to stash income in tax havens.

If that urge to cheat ever comes back, consider paying an accountant so you can cheat legally and without repercussion!