I don't think AI will ever be able to nail jokes all the time. But I could easily see it being able to go over an email and suggest a couple jokes here or there

I don't think AI will ever be able to nail jokes all the time. But I could easily see it being able to go over an email and suggest a couple jokes here or there, which you could accept/reject/edit. It would be interesting if you interacted with someone for years over email, and then finally met in person and found out they were not funny at all. Put that in a dating app and it's along the lines of using filters on your photos. There's more than one way to be a disappointment in person.