Explain xkcd: It's 'cause you're dumb.
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Prior to the events in this comic, Cueball has evidently told Megan that he made an assumption about something. Megan starts to respond with what seems to be the modern proverb: "When you assume, you make an ass out of you and me." This proverb plays on the fact that the word "assume" may be broken down into the letters "ass", "u", and "me", and is intended to suggest that one should not make assumptions because they may turn out to be wrong and make those involved appear foolish.
However, after Megan relays the first half of the proverb in the form "You know what happens when you assume", Cueball astutely points out that her phrasing itself is hypocritical in that it makes the assumption that he knows what happens when you assume. Megan stops to ponder Cueball's point, to which Cueball responds "Check and Mate": a common phrase (originating from chess) suggesting triumph or having successfully countered another's argument to which there can be no retort.
In part, Cueball's response demonstrates that, in life we make assumptions almost every time we speak. This only tends to be problematic in the few instances where the assumption is wrong.
The title text is a play on the original "assume" pun, breaking down the word "assert", into "ass" and "ert", with "ERT" being an acronym for "Emergency Response Team".
- [Megan and Cueball talking.]
- Megan: You assumed?
- Megan: You know what happens when you assume-
- Cueball: I don't. Yet you're confidently asserting that I do.
- Megan: ...oh. Hm.
- Cueball: Check and mate.
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