That’s not a dumb question! If you had a good answer to it you could write a book and make millions!
Jokes aside though, I know exactly what you’re talking about. I’m much the same. I’ve worked a lot on it, and phero’s have helped me significantly, so I’m at the point where I’m fine chatting to people in general, and to guys that aren’t really my type…But I still get that weird mental paralysis if the guy in question is someone I really like… Lord knows I’ve said some weird stuff to my ex-TG 
What I’ve found though is that practice really does make perfect (even though I’m not quite at perfect yet). Practice small talk with people in general first, then move on to girls that aren’t in the category of girls that “You’d just looooove to go out with”. The beauty with that is that you feel less pressure when the girl you’re talking to isn’t really your type, when things go right you get a great ego & confidence boost, and if things go less well it matters a lot less as you weren’t really that interested in going out with the girl anyways. Once you get comfortable talking to people in general and random girls then move on to the ones you’d actually like to ask out.
I agree with you there. I’m sure the PUA stuff is great for some guys and that it works well for them, but a guy who’s really nervous about talking to you, and who’s personality just isn’t inline with the PUA stuff, well if he tries those tactics on you it just comes across as so desperate and “cheezy pick-up line-ish”.
You’re a lot better off just trying to combat the nerves and being yourself. If a cute girl starts talking to you, or you approach her just try and relax and be yourself. Talk to her like you’d talk to a female friend/sister etc rather than try and jumping straight on to the flirting.
Well, unless you’re wearing someting utterly ridiculous (I’m talking something that would make Steve Urkel look like a stud) then you can pretty much assume that if a girl keeps looking at you then she’s interested. If she keeps looking at you but look away, look at her feet or blush whenever you catch her looking at you, then she’s not only interested but a kindered spirit in that she’s too shy to approach you… So you’ll have to be the ballsy one because she would love you to make the first move!
I have to say that even though I don’t get approached a lot, whenever it does happen it really brightens my day, even if it’s a guy that I’m not at all interested in. Just having a guy look at me, smile and say hi can easily make my day.
The only thing that I’d personally class as “socially unacceptable” is really lewd oogling, sexist jokes and cheezy pick-up lines… a guy who does that puts me off.
That’s awesome! Use that to your advantage!
I would have thought that it would be quite easy to work the fact that you’ve lived on 3 continents into a conversation…AND it’s also always great to steer the conversations to topics that you’re comfortable with and know a lot about…it relaxes you and allows the conversation to flow more naturally.
Depending on what you’re already talking about you might be able to just slip it in to the conversation, but if not… wait for a few seconds of silence, then start a new topic with a question that would allow you to shift the conversation to you having lived abroad. Ask if she likes to travel? Where’s her favourite place to go, or what’s her dream holiday? Since you’ve lived on 3 continents odds are whatever her answer is it’ll be someplace where you’ve either been or that’s close to somewhere that you’ve lived…so you could easily add “Oh, that’s a great place. I used to live in X” and go from there 
If you start talking to a girl, (or one approaches you), just be yourself. Smile at her, say hi and ask how she is. If she approached you then she’s obviously interested in talking to you and probably has already thought of a few conversation starters, so let her take the lead.
If you approach her, then depending on where you are you could always ask her if she’s waiting for someone, if she’d mind if you join her (eg if you’re in a cafe, lunch canteen etc). Very, very few women would say they would mind if you join them…so park your butt with a smile
If you asked if she was waiting for someone and she did say that she was, then give her a big smile, say something like “oh well, I’d better leave you to it then” but also add something like you thought she looked like a really nice person & that you figured you’d chat to her for a bit…then smile again and leave with a “have a nice day”.
Once you are chatting to a girl just keep a few things in mind…
- Be yourself, don’t try to act suave or do the PUA thing
- Smile a lot
- Listen to what she’s chatting about & to show her that you’re interested in what she’s saying throw in a few questions about whatever she’s talking about
- Once you’ve talked for a while and if the conversation is going well, give her a compliment or two…genuine ones, not cheezy pick-up lines. Doesn’t have to be about her appearance (those can easily come across as PUA type compliments) but could be a response to something she’s done where you can compliment her by saying “that’s really impressive/interesting/brave” depending on what it was she’d accomplished… a degree, bungee jump or what have you