Depends on 100 variables. There are books about this simple question but allot of it is BS. Be confident, dont use Neg's and Do not over complement. I guess i'm full of dont's because the Do's usually aren't planned..If you are gonna straight ask her out DONT do it for something big, dinner movies etc, do make it something not distracting like coffee, yogurt then that morphs into a walk or adventure.Seek out something different than the last guy, do something off the wall to set yourself apart. I take girls 4 wheeling to the top of a peak above Tahoe city were you can see everything, its always a win.
I like to come up with missions, " your in no hurry right, lets find the tallest building in town and try to get on the roof" You don't connect by watching a movie together, the longer the conversation you can have the better connected you get and shared experience of adventure is 100X better. Just be confident and do be anything other than the best you you can be.