Hi! If I'm understanding correctly I would do it like this. The first part is a little involved, but if you have some knowledge of functions it's not so bad.
1. Make a function separate from the event_handler that randomly checks if a boy wants to ask you out and then calls a label for that.
2. Make said label for being asked out. Use dating.tryst_setup() before the menu that asks if you want to accept the invitation with the boy. Then to make it for the upcoming weekend do dating.confirm_date("Name of boy", dating.p[0])