well after the date.... if things have gone well and your into the other person then...wait a day.... and call to see what there up to... then you can ask them out again...

Things like holding hands and all that stuff comes usually by gut instinct.... and looking for signals..... If she seems into you... and is laughing and smiling and gently reaching out to touch you..then you could lightly grab her hand as you walk her home or something....

Always trust yourself and your gut.... really feel out the energy of the situation..and dont think so much..... Relax..and Im sure everything will go well.... You sound like such a great guy asking such cute questions!!!

Hopefully at some point you will have someone in your life that will be willing to work with you and not against you in a relationship. Sometimes it's easier for me to be assertive with someone who is generally an easy and gentle person. This guy you are with doesn't appear to be either. I think I might have a hard time speaking up to him myself. So don't feel bad because you feel it's hard to speak up. It's just easier to do with some than others. You'll get there. Best wishes.