The Redditor who posted this provided little context beyond the post's title, "Cheating Boyfriend sent on a scavenger hunt." We'd love to know a little more. For example, once the "loser boyfriend" completed this hunt, was the infidelity forgiven? Is it really a good idea to punish a cheating boyfriend by making him go up to strange women and do nice things for them, at which point he'll probably have to explain that he cheated and is being punished, which basically announces to them, "I am historically unfaithful to my girlfriend, so if you want to sleep with me after I do something nice for you, that's an option."
Also, "Ask a woman wearing high heels to massage her feet?" This is a sex game, right? He cheats. She commands him to go out and humiliate himself by wearing women's clothing. This is a dirty little game for a couple who gets off on punishment and public humiliation and they're probably masturbating to you reading this right now. Sorry to involve you in such a sick, twisted game.