Played this with friends and it was absolutely iconic.
For starters, I'm actually not sure what the game is called - the steam page suggests both "TryAndLove" and "I Have a Date with a Beauty".

This game suffers (or benefits) from a horrible translation which made the plot nearly incomprehensible. You had to kinda guess what each dialogue option could mean and even with context clues, it was hard to tell. The Dark Souls of dating games, if you will.

Here's what I think I know:
Our best bro is either an escort or some kind of e-sports player. We also might be his sugar daddy.
One of the love interests might be a news anchor or a dancer on a streaming platform. She's talking about getting PKs a lot, which I interpreted as player kills.
Our childhood best friend might want to fight us in a park. I think we were also in a fake relationship to appease her father?
Another lady is our former teacher and she has a brother. You can touch her brother's leg for no reason and she loves it. At some point, the brother turns into your brother. The family dynamics are pretty confusing with this one.

The comedic value of this game is immense, although I don't think this was planned by the devs.