Ok, that was long. You may want to condense future posts... You'll get a lot more replies.
Welcome to the forums. I'm happy to hear you want to learn.
The bigger the city, the easier it is to do pickup IMO. NYC is perfect.
Your age does not matter. Lots of older posters here. Successful older posters.
Overall, from this giant post, I'm spotting that you're working through email and text a lot... and you need to....... not be doing that. It's fine to stay in contact, build some interest and make her laugh a bit, but you need to be calling them and seeing them in person.
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The Questions:
(1) So, if a woman ignored the first text (2 days later) should I just move on, or give it a try one more time 5 days later?
Try again. Nothing to lose. Ignore the first message(s) you sent. Don't mention them at all... Make the new message about something completely unrelated... Or call her instead.
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(2) is it okay to do a slight neg in the text/email - but one that ends on a positive or funny note?
Sarcasm=OK... Negs=No. Stay away from them unless you know you can deliver it really, really well and it won't be mis-interpreted... You probably don't even need to use negs at all, honestly. They're meant for 9s and 10s... to knock them down a peg. Negging anyone other than that, who isn't being a bitch to you is just pointless and won't get you anywhere.
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(3) Should I ask them out on the first time I contact them - I've tried both ways and still not sure what works.
That's something you need to gauge yourself. Really depends on the girl and how your interactions are going. If she's SUPER receptive, laughing at everything you say, and replying with a lot of messages, that's a good sign. When she's the one starting the conversations, that's another...
Again, call - I get that you're a writer... call anyway. Way harder for them to say no... and you're also not left with the problem of question #1 (above) where they just ignore you... at least you'll know, one way or the other.
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(4) Should I ever slide the car brand name into conversation?
I had the balls to recently talk up a tall hot blonde runway model who gave me her number (on the auspices I knew someone in casting) but she ignored my short casual text.
Should I as a last ditch effort offer to take her to some cool destination in my Porsche? (I would even be happy to befriend her to be able hang out in her model filled hostile)
Or is this asset better left to impress girls only when they see it as I am picking them up on a car date (which is generally not the first date)
No. Just no. An older, used Porche? C'mon... you can DHV yourself better than that. Don't boast about an old car. Unless she's a petty little girl she won't give a fuck what you drive... (if you had a late-model Ferrari, my response may be different).
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(5) I tend to almost never complement a girls looks, since I feel they hear that all the time. I may complement her earrings, etc or say I believe in her future at her job/company, but try not do the typical crap guys do. But should I being saying in a text or email I find them attractive, easy o the eyes, etc to let them know I don't see them as a friend?
It's fine to let them know they're hot. If they actually are hot, they already know. Complimenting accessories is a great idea... It's indirect. Always have a reason to compliment... IE: "I like your necklace, it matches your eyes" as opposed to "I like your necklace"