Legal Dare #1: Use Wingdings in a Letter

Gregory Luce Lawyer, Legal Dare Leave a Comment

It’s time for Bitter Lawyer’s weekly legal dare, a challenge to lawyers who remain a bit bored and jaded at the office. For #1, we legal dog dare you to send opposing counsel a letter, complaint, or interrogatory reply using only Wingdings or Dingbats as the font. Some basic rules are below (e.g., e-mails don’t count).

If we can verify that you actually completed the dare, we’ll happily send you a $25 Amazon gift card, but we won’t vouch for you in any subsequent ethical proceedings. That’s not within our paygrade or jurisdiction.


Some Rules

Listen, we don’t want to litigate over a lousy $25 Amazon gift card, so here are some basic rules.

  1. It’s in Bitter Lawyer’s sole discretion to award a gift card. We thought about adding “sole and exclusive” but that’s overkill. Just us. We the man.
  2. For this particular dare, only items printed and sent by mail on real paper count. Wingbat emails are too easy—lawyers do that all the time already. Yes, you can address the envelope with Times New Roman or some other appropriate postal-approved typeface
  3. The first lawyer or paralegal human being to send us proof of a completed dare is eligible for a gift card. Notice how we said “eligible?” That means we still have the ability to verify whether you really did the dare or not.
  4. Proof must be forwarded to us by email to and could come in the form of an image, affidavit, blood oath, deposition testimony, or crowd-sourced verification by at least 10,000 people.
  5. If there is a tie—and we’re still not exactly sure how that would happen—we will use traditional trial by fire rules to break that tie. We may also consider any available Monty Python method of tie-breaking. We choose.
  6. We can change these rules at any time. This always seems grossly unfair but, hey, everyone else does it that way. We asked.
  7. If you have a suggested legal dare, we’re all ears. Send it to us by email ( or send/post it on Twitter with the hashtag #legaldare.

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