The interaction Deep Conversation is missing from the friendly menu although my Sims are friends and even have a romantic bar. This makes it impossible to fulfill the tasks for dates.
The interaction can have different names depending on the situation. If Sims are confidants (?) the interaction is renamed to Share Stories of Personal Challenges and when it’s Talk like a Pirate! Day, it’s called Exchange Pirate Yarns.
Because of a bug the interactions is called Share Stories of Personal Challenges for everyone though if you don’t have Snowy Escape installed.
When on a date, simply use the interaction Share Stories of Personal Challenges or Exchange Pirate Yarns. This should fulfill the goal.
Please click me too on this thread if you’re affected by the issue