""You didn't almost lose pretty badly," May said."
Is that a typo? Robin did actually lose, rather than almost losing.
When Robin originally asked the question, she said, "I did lose, and almost pretty badly at that, so I get it if you weren't that impressed." She's there referring to the fact that she nearly lost 2-0 (she had only Charizard left while May had Tyranitar and Floatzel, but then her Charizard managed to take Tyranitar down, despite the huge type disadvantage, and ultimately put a dent in Floatzel as well).
May is responding to that statement, saying no, that wasn't almost a pretty bad loss, that was almost a win. It's kind of a glass-half-empty situation - Robin feels she only barely scraped her way to a respectable 1-0, whereas May feels Robin was dangerously close to beating her.
There is now a character bio for Robin, given she's catapulted herself into the main cast and all. Right now half of the character ramble is about May, because so far Robin's primary purpose is to torment May by existing and Robin herself is fairly well-adjusted, but hopefully it's interesting anyway. (The other half is about Robin's origins as a character and is a shining example of how most of this fic's construction consists of miraculously happy accidents.)