The thing is, even if your grandfather insists on going on a first trans date with a woman, the world of online
transgender dating has made it less common. Since you are essentially strangers before shaking hands or hugging, asking to pick her up can be taken for granted. Still, try to find a place, like a restaurant, bar, or cafe, where
trans dating is more acceptable to her, spira suggests. She'll feel safe meeting you there, too.