I couldn't come up with a better title, but basically here's something I ran into recently while being "in the field" during the day. Per one of your suggestions, I'm trying to spend more time in coffee shops to get used to talking to strangers and to strike up conversations with HBs, but I ran into this issue: Let's say a HB walks in, is ordering coffee while you're sitting reading or some other shit. Ok let's say you get up and go next to her to strike a conversation like "Man, so many options, what should I order next? As a pro, what would you get if you were me?" (just something random Wyganty to get things going).

Now let's say nothing happens, then the next HB walks in, you can probably do it again if you have another excuse up your sleeve. But then, let's say you're not too picky and you're just practicing opening, anther girl walks in.. There's only so many times you can get up and walk up to someone who just came in and strike up a casual conversation, before you come off as a weirdo to everybody around you. That or the owners of the coffee shop, which of course you should have befriended by then (the be a mayor of your life stuff), will remember you as the "guy who tries to pick up chicks in our shop".

So on one hand, you don't want to be the guy who is letting opportunities walk by, on the other hand, you need to go easy on the creepiness factor. If the HB sits down next to you and starts doing shit, yes it's very easy to start a conversation, but this is quite similar to approaching someone at the grocery store or on the street in the same location, you can only do it so many times before it's weird. Or can you? Should you be changing locations all the time?