You need to leave the house and when you go out into town you will run into your father's coworker. You also need at least 5% femininity for it to trigger (Also at least 10% for one of the options in this encounter, but that isn't required to continue the storyline).
Oh, sorry, for this specific path, you do need to play a feminine character, HOWEVER, if you specifically play a masculine character, at -5% femininity you will be able to just interact with the PC parents without playing through this sequence, however it won't really complete this objective as it's sort of the setup for the feminine side.
So you can do the content with a masculine character, this objective specifically is just the feminine path introduction to the parent's content, sorry for the confusion.