I’d say she already gave him a chance - she said “yes,” after all. He was so close, he just needed to use his own brain and put a little personal effort into planning the date. He could’ve even been honest about not knowing what to do and said something like, “I’d like to have some of your input to make our plans. I was thinking of a movie, but there’s a museum not far from me. The park’s really nice this time of year, too, if you’d prefer to be outdoors. Do any of those sound good to you? Do you have any ideas to add?”

I mean, that’s what I’d do. It’s not hard to think of things if you know a person a bit, but if you don’t know them well enough yet to know what they’d like, that’s okay too! Make it clear you want something you’d both enjoy and turn it into a discussion. No AI is going to know what she likes better than she does, so just go to the source.

And if that’s too much effort, then perhaps dating in itself would be too much effort.