Sounds to me like you are afraid of screwing things up and therefore viewing pickup as a chore rather than good time. The truth is, screwing up is a great way to build attraction. In fact, it's a GREAT way to build attraction!
Why? Write this down in big bold letters and post on your wall where you can see it:
EVERYTHING IS RECOVERABLE!
Every situation is can be recovered given enough work and time. The question becomes whether you want to put the time and effort into it. Think I'm nuts? Play this game with your buddies next time you are at the bar:
get at least 3 of your buddies together
1. one of them makes up a character (007, bugs bunny, underpaid stripper etc.)
2. another buddy makes up a pick up line (emmmmm....what's up, doc?)
3. your third buddy picks out a set
4. you (or whomever turn this is) has to start interaction in character and use the pickup line. You can't tell the target set after delivering the pickup line what game you are playing. (You can tell them later if they ask or the set sticks)
If you chicken out you have to buy a round of drinks.

whether you run out of money or have a great time is entirely your choice. The sets tend to be fun and interactive. Make a fool out of yourself and watch, in disbelief at first, how easy it is to recover. Notice how much, except for you, really gives a damn XD.
Hope this helps,
Al