I'd tell him to show her his meme collections, but given how you describe him, he probably doesn't even know what meme is. Damn normies.
Just keep dating. Goodie two-shoes doesn't have any reason to stop. Friend must advice just that. And after that meet in secret with "the madame" and tell her : leave him. He's in love and too good for you.
Make sure he is wearing a condom when they are having a consensual sexual episode, provided the lady is at least 18!
An update for anyone curious about how this would turn out: It resolved in about only four dates, much faster than we were expecting. XD It turned out that he missed his chance to ask her on the third date at the end of the second, so he actually didn't have any obligation to go on another with her. His friend gave him the advice to let her go. He decided to completely stop listening to his friend, though, and scheduled and arranged the third date all on his own... He remembered her saying that she'd put "trying out swimming as a mermaid" on her bucket list after they briefly talked about professional mermaids on their first date. So, without anyone's advice, he booked a mermaid swimming lesson for their third date. ... Anyway, she came back so starry-eyed, it was like she was a different person entirely. And he made their fourth date present (the men have to give a present every date) more lessons for her, and all the stuff she'd need to get started. So she's pretty much decided he's the one for her. In one of the strangest plot twists I've had to write, he won her love and trust with the power of mermaids? XD (Also by not kissing her on the third date like she expected.)
@Moonpearl I’m really curious, but what kind of game is that you’re playing? I’m curious about the rules and how’d I’d be able to play it with my own friends!
It's a roleplaying game that my friend and I just make ourselves. It doesn't have official rules - there's also no system or book we use. It's pretty much the same as collaborating on a story, only you write back and forth in turns, and you're limited to controlling your own characters. (So it doesn't read well to outsiders. XD) We've been playing this way for years. This particular game here is my friend's idea - a fusion of sports anime and "Princess Princess". Spoiler: Briefest explanation of the game I can give It's set in an extremely prestigious all-boys boarding school in England. If you attend there, you're basically guaranteed an easy future. The school also has a "princess" system that's been in place practically since the school was founded: the school provides many scholarships to boys who can't afford to attend and, in return, they live their lives as girls while there. The "girls" are "princesses"; the normal students are "princes". The idea is for the rich boys to play-date the poorer boys to practice courting real women in the future. In reality, nobody uses it and it's a huge drain on the school's resources, so the headteacher made it mandatory this year. Also, as the game has progressed, it's become apparent that a lot of the "crossdressing boys" are actually trans women undercover, so... The setting changed a little so that you never know if the princesses are boys, girls, or otherwise. (We designed it to be yaoi, but it went rogue~!) All our characters also join the water polo team. We're not quite into the sports anime bit yet, but I'm pretty sure we're supposed to be playing a parody team, and not the team you'd expect to star in a sports anime. Like, 80% of our team is just there to flirt and doesn't care about the sport at all... Spoiler: Making games If you want to make a game like this, you need to start off with an idea of the game you want to make. You can use just random ideas, fusions, or make fan games (we have our own version of Yugioh GX, for example). We even have a game called Crossover that's just about our characters (with their own mission and plot) travelling across different books/films/TV shows. Usually the person who came up with the idea builds the rest of the game world. The other players build their own race(s) or country/countries if necessary. How much worldbuilding you need to do depends on your story, of course - fantasy worlds take more than modern settings. I recommend not building the entire world for fantasy settings, either - just the couple of countries you'll be based in and a general idea of the world. You can always add more as you go. Then you create characters. We usually use anime pictures that we pull from the internet, but you can also just use descriptions. How many each player has depends on the game, the players' interests, etc. They have to be about as developed as you would make them for a story you were writing. (For this game here, I have 6 - 3 princes, 3 princesses - and my friend has 9 - 5 princes and 4 princesses. That's because she wanted to create a surplus so I could pick my favourites~!) And then... Well, you just write. We use brackets to talk to each other while we're playing so we can decide what to do next, laugh with each other about the game events, talk through things that aren't going as well as we planned... We usually talk about it after we're done playing too. Personally, we divide individual games into arcs and scenes. The scenes let you pass over days, skip between different locations to different events happening at the same time, etc. We pretty much always keep those in chronological order, otherwise re-reading the logs get difficult. The ends of arcs are good stopping points if you want to take a break, good excuses to skip over months or years at a time, and also they trigger the start of a new log, so those aren't too lengthy. We play on Facebook messenger and I copy every reply into a Word document, turning my friend's moves red and leaving mine black. I also keep a separate document for time pass, where I record the years/months/days/etc. gone by since the start of the game, the time that an arc ended and began and the time we skipped over in between, and important dates past and present - such as birthdays, or when a character became pregnant and is due to have the baby. When I really need to use some sort of reference to real-world time, I pick a year in history and use the calendar from then. A lot of our earliest games (and even some we make now) were based on arranged marriages, so you could try starting with those if you get stuck. But really, you tailor it to your own tastes~!