I read your last few posts. I don't have any tips for you, but your posts did give me some food for thought. What would I do if my WW wanted to date me? (Um yeah, that's never going to happen.)
I've changed so much that I have difficulty imagining dating my wife. I'd certainly make my WW pay for the dates. Assuming we'd go to a restaurant, I'd probably hump her leg at the restaurant just to create an embarrassing scene. Then maybe we could go to a movie and I could dump popcorn in her lap. And at the end of the night, I'd get her to pull my finger and then have her Uber herself home. In other words, I'd try to make it an unforgettable evening.