Have you ever seen "My Fair Lady"? There's plenty of others, but this immediately occurred to me as being the archetype as I read.
Archetype for the movie "She's All That" with Freddie Prinze Jr., that is; I was reminded of that movie upon reading the description, and, feeling some nostalgia, had decided to check out the story.
What I can say, thankfully, is that this is substantially better than the 90s movie, and it's also different in a few key ways, though the basic premise that it inherits is the same. The main character is challenged to a bet that he can have sex with a girl at random, and he's enough of a dick here that he accepts. He manages to go through some nice character development through the course of the story, and the ending was a good fit. I can't say any more without ruining obvious plot points, so I'll stop here.
One of the things which was especially good in this story was the dialogue. It characterizes the people portrayed very effectively, and the back and forth between the main character and his best friend is pretty funny at times. Also well done was the female lead, who is a little different than I expected - though not by much.
There's barely any stroke here, don't bother if you're looking for it.
Technically, this was well-written. No errors found, though I'll admit I wasn't looking very hard.
As I said, this plot is not original (though it's surely possible the author has never seen any of the previous instances), but the author does enough with the characterizations to keep it fresh.
This was a good read. The characters are engaging, the plot does have a couple unexpected turns, and it ends effectively. I recommend giving it a try.