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There is a literary technique in comedies where a person says something intending for it to be reassuring and confident, but their words are humorous because when interpreted differently, the phrase could mean the opposite.

An example: In an adventure story a character Joshua is known for being clumsy and causing accidents. He convinces the captain to take him along on a journey. The captain says, "Okay, but you'll have to keep up, we can't have anyone slowing us down." Joshua says:

"Don't worry captain, with me along that will be the least of your concerns."

As you can see, Joshua meant to say "You shouldn't be concerned about me slowing you down," but he also somewhat implied "I'll cause greater concerns for you than slowing down."

Is this an example of irony? Is there a more specific term for this kind of humor that is accidentally self-deprecating?

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    It can't really be irony, or any figure of speech for that matter, since it is unintended. It is perhaps best described as a faux pas (false step). – WS2 Jul 29 '17 at 17:44
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    @WS2 You'll notice the OP mentions 'a literary technique in comedies' - sounds purposeful by the comedian, just not by the subject of the story (maybe dramatic irony in which case?) – marcellothearcane Jul 29 '17 at 17:59
  • Wikipedia allows the broader sense of 'double entendre', which, however, still does not demand the element of self deprecation: <<A double entendre ... is a figure of speech or a particular way of wording that is devised to be understood in two ways, having a double meaning. Typically one of the meanings is obvious, given the context whereas the other may require more thought. The innuendo may convey a message that would be socially awkward, sexually suggestive, or offensive to state directly.>> – Edwin Ashworth Jul 29 '17 at 23:47
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    humblebrag--trying to brag about yourself while tacking on a remark affecting humility. Example: 'I'm a legend...in my own mind'; 'I've always had a restless urge to lie down'. – user3847 Jul 30 '17 at 4:32
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    User3847: That's not what humblebrag means, quite the opposite. It's people using false modesty as a context to tell you just how great they are. Definitely not the case here. (E.g. a boring one, but typical at job interviews: "my biggest flaw is being a perfectionist...") – mick Jul 30 '17 at 18:05
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As stated above, the basic device is double-entendre.

It might also be dramatic irony, but only if the reader/audience is aware of the full implications of the double-entendre, while the character being addressed is not aware. http://www.bbc.co.uk/schools/gcsebitesize/english_literature/dramaothello/3drama_othello_dramarev4.shtml

The character who is unconsciously revealing his shortcomings may also be making a freudian slip.

I don't think there's a single term for a device that incorporates all those elements, though.

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Wikipedia allows the broader sense of 'double entendre', which, however, still does not demand the element of self deprecation: A double entendre ... is a figure of speech or a particular way of wording that is devised to be understood in two ways, having a double meaning. Typically one of the meanings is obvious, given the context whereas the other may require more thought. The innuendo may convey a message that would be socially awkward, sexually suggestive, or offensive to state directly. - @EdwinAshworth

Comical sums up the wit, surprise, double entendre, paradox, humor, and delightful silliness of the reversal. Wall Street Journal had a piece once on ambiguous job 'recommendations': For the useless—We can recommend her without any qualifications whatsoever. For the lazy—You'll be lucky to get her to do any kind of work. For the dishonest—He's a man of many convictions. - @YosefBaskin

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I would call this an "unwitting comedian".

http://wxrt.cbslocal.com/2015/09/23/lin-brehmer-remembers-a-yogi-berra-he-could-never-forget-listen/

For all his on-field accomplishments, it was Yogi Berra, the unwitting comedian that people remember. Yogi was what is known as a bad ball hitter. Frustrated with his lack of discipline at the plate, manager Casey Stengel once told him to think when he was at the plate. After whiffing on 3 mighty swings, Yogi walked back to the dugout and uttered a line that would be at home in the ashram of a perfect master. He said, ‘how can I think and hit at the same time?’

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