On a Plane
As a general rule of thumb, scenarios where a woman is trapped with you for hours at length is a bad place to make your move. She’ll muster up a few one-word answers to your prying questions about where she’s going. She may even feign interest, and nod knowingly when you explain that you’ve chosen What to Expect When You’re Expecting as your in-flight reading because you think it’s important to relate to women’s unique struggles.
But recognize: It isn't because she finds you attractive, or because you’re a skilled conversationalist, it’s because she literally has NO WAY TO ESCAPE. Let her bond with her neck pillow. If you can't pass her up, chat with her while you're both waiting for luggage. You know, somewhere with visible exits she can use if she chooses.