This is tricky. But, I found out that you can only go on a date at certain venues.
What you do is create a date the same way you'd visit a lot with someone. So, you ask the person on a date. Then, once they agree, go to the community lot screen and select a venue. The movies, bistro, and places like that are not dates. It has to be more communal, and I think not a rabbit hole. It has to be a place like the pools, gym, art gallery, parks. This is because you have to be able to control what happens on the date for it to be a good one. So, no rabbit hole spots for a date.
I think that's it. It worked for me last night.