My entry:
The girl I like promised to go out with me if I will successfully beg for 100000 upvotes. It took me twenty years and finally I am very close to reaching this goal of mine. I just need a few more upvotes and my life mission will be completed. Bro plz don't be a cockblocker and give me that upvote...
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I'd be tempted to flag a pitch like that. Why? Because it would probably be in the best interests of the guy. The entire frame of the interaction between the girl and the guy is cringeworthy.
At first I also wanted to add something about prohibition to get closer or testament that leaves all property to those who supported his goal. But then I decided that this is already cringeworthy enough
Yeah, the art of begging is straddling a fine line between sounding pathetic enough and over the top pathetic. :D