What would you recommend, and what is your reasoning behind your recommendations?
Maquia When the Promised Flower Blooms
A great heartfelt fantasy movie
It's just a funny comedy, a good laugh. Although I don't know if you'd be able to finish the entire anime, but this is a type of anime where there is no build up in the story. The first episode is just a introduction and one scenario or two. After that it's just, watch at your own pace.
This has been tested in a date, and it ended with a success:) so give it a try.
It's quite a emotional movie, that can be a good thing, if you're both into that.
My friends enjoyed this movie, I wasn't a fan of it but, the majority seems to like it, so I am putting it out there for you.