This is just going to be a condensed version of my last 40 or so approaches.

Drove 80 miles to buy some new shoes at an outlet mall. Look around and spot HB9 walking opposite of me. I walk by her, double-back and go direct. Transition with an introduction and handshake. Start talking about what brought us here, I say some shit about Santa which I thought was funny. Rift on that for about a minute, notice I'm losing her attention then jokingly suggest she shop with me. Says no and then I play it off by saying it would look creepy had she said yes. Blah blah blah go for the number and get it. Then I said the worst thing possible in an attempt at humour. "I'll give you a ring so you know it's not that creepy stalker every girl has. Trying to get over a sticking point did work, but found another way to mess up the set. Lesson to be learned: Avoid using the word creepy or stalker when approaching. Also I seem to have trouble remembering to inject statements of value and qualification into the conversation. Fuck it, I'll create some canned material.

tl;dr You can say stupid shit, but avoid words like creepy and stalker.