It was awful. One of the worst thing I ever have to do. Especially when it's a girl who has been genuinely sweet to you, but you had to move on for other reasons. I've never heard someone cry so hard. Man it hurt to do that...

You've replayed it a hundred times. She stood three feet away, scrolling her phone. You had an opening. You composed the perfect line — after she was gone.
For all you know, she's married now. To some guy who said something. Anything.
Openers are cheap. Almost any sentence works when it's delivered within three seconds. The expensive part is the standing there, drafting and deleting, while the window quietly closes.
The "22 Rules" stripped out my hesitation. What to open with, how to keep it alive, and the one habit that costs guys more women than anything else: waiting for perfect.