>>24014302you have an hour but can you pick when?
What I'm getting at here is you will be 500% more successful if you do it when she is menstruating. You even have someone in the know who can give you the timetable, although you and him will need to negotiate whether that constitutes an unfair advantage.
>outlined the rulesWhat are the ground rules? Are you allowed to hit her? You could "accidentally" hit her in the or even just playfully challenge her to a game of punchies like you are going to go easy on her but then go full blast into her bicep. She will cry for sure.
Are you allowed to implicate your friend in this? If you really want to win the bet nonviolently then telling her all the details of the bet and that he wanted her to cry, bring proof of the arrangement like texts from him that she can look at so she knows this isn't fake. If he wants this to happen to her he has no right to complain he obviously doesn't care about her at all. If this doesn't work then it would probably tell you she is already in on the whole arrangement and it was fixed against you already.
>The stakes involved are my honorHow ironic, I think you and her boyfriend are both despicable and dishonorable cads for wanting to make her cry for fun. Even if your friend thinks you would be a kill joy you could score easy points with everyone you know for not participating in this sham bet.
insulting is a good option but you don't need an explanation of that. Doing it enough and in the right ways will yield a pretty quick victory.
There are honestly some really easy solutions you could try like if she likes anime or something find one or some short film that can prove to be a tear jerker in only 20 to 40 minutes, find a song that always makes her cry or whatever.