How do you hold hands with Elise after she asks you to go on a date in Fable 3 and what if that does not work?

Step away, then step back and you should get a prompt to hit the Left Trigger. The UI in Fable 3 is VERY WONKY. You often have to move around a little and hit a button several times for it to work correctly. Sometimes, after you are holding hands, it will look like you let go. This is if someone walks between you, you are running up stairs, or other similar actions. When you stop walking, you will still be holding hands though. In order to let go, you hit the lower left trigger again.