8 Ridiculous Drawing Challenges to Send Your Friends

The quick answer: pick a prompt below, open its link, draw it, then send the same link to a friend and make them do better. Every prompt is a DrawDick challenge link, so whoever opens it lands in the editor with the challenge already set. No account needed.

A prompt does something a blank canvas cannot: it gives the drawing a job. "Draw a dick" gets you the shape. "Draw a dick at a job interview" gets you a tie, a nervous sweat drop and a résumé with one line on it. The joke is in the situation, and the prompt hands you the situation.

1. The job interview

Everyone has sat across a table from someone with a clipboard. Give it a tie that is slightly too long, a folder clutched to its chest, and a face that is trying very hard to look like a team player.

2. The midlife crisis

A convertible is the classic, but consider the alternatives: a leather jacket, an earring, an electric guitar it cannot play. Bonus points for a younger, cooler friend it is clearly trying to impress.

3. The tax return

Paperwork is funny precisely because it isn't. Surround it with receipts, a calculator and a single desk lamp. The expression is the whole drawing: try exhausted, defeated, or suspiciously cheerful.

4. The medieval monk

Medieval manuscript painters filled the margins with things that had little to do with the text, as the history explains. Draw it in that style: flat colors, gold leaf (yellow will do), a decorated first letter and a rabbit that looks slightly menacing.

5. The film noir

Black and white, a trench coat, a hat pulled low, rain on the window and one long shadow across the floor. Stick to black, white and grays, and on a computer let the spray tool do the smoky light.

6. The weather forecast

A presenter standing in front of a map, gesturing at a cloud that is suspiciously shaped. Add the little sun and rain symbols. This one works because the setting is so ordinary.

7. Leaving the group chat

The quietest exit in modern life. A phone screen, a stack of unread messages, and a small figure walking away with its back to the reader. Sad, dignified, slightly smug.

8. The magnificent moustache

A moustache changes a whole face, and on this one it is the main event: waxed tips, a curl at each end, or a walrus that hides the mouth entirely. Give it a comb, a mirror and an expression of deep, unearned pride.

How to turn it into a game

• The relay: one person draws, then sends the link on to the next, who has to draw the same prompt better. The last one in the chain picks a winner.
• The timed round: everyone gets the same link and sixty seconds. No undo. (There is an undo, but agree not to use it.)
• The swap: each person sends a different prompt to a different friend. Compare the results at the end and argue about them.

Frequently asked questions

Does my friend need an account?

No. A challenge link opens the editor for anyone, and they can download what they draw without signing up. An account is only needed to submit a drawing for review, so it can be published and rated.

Can I pick a random challenge instead?

Yes. The Challenge a friend button on DrawDick's home page picks a prompt at random and makes a link for it.

Is there a new challenge every day?

Yes: the Daily Dick sets one prompt a day for everyone, and shows yesterday's winners.