First, let me commend you on taking a shot...when hitting on women, you never lose, you either win or learn lessons and get better while enjoying yourself in the process. I've got a bunch of thoughts so I'll just pour 'em out in no particular order. They're not as philosophical as some of the other comments but more tactical.
- If you're vibing, before she gets a chance to disappear, get her social media contacts like on instagram, fb, or kakaotalk. It's like asking for numbers these days, but also easy to do if you segue into it naturally, like talking about how everybody's obsessed with instagramming these days. you can then contact her later or at least have memories of her. and screenshot those, bc they may well unconnect or block you later.
- I do think she just met an interesting person on the day before her flight and enjoyed the experience...that's part of seeing the world. I don't think she was looking for money or to have sex. Young hot upscale girls are rarely rarely trying to hook up with a much older man. doesn't mean you can't try.
- having said that, you definitely could improve the escalation techniques and make it more natural and with less negative consequence if it doesn't work. done naturally, the worst case scenario is an enjoyable night out, lots of flirting practice, and a hug goodbye with the possibility of more.
- asking to hold hands suddenly is a bit abrupt and unnatural. if a girl wasn't interested to begin with, it'll make it very awkward. much better to make the escalation more natural like when joking and both are laughing, lightly touch her upper arms casually. or engineer a situation where there is mutual agreement and enthusiasm and high five her. any contact is the beginning for escalation (classic pickup artist techniques that I've used even before i knew it was a technique)
- slowly and naturally increasing the amount of physical contact will make the next step more natural. don't make it obvious and there's no guarantees with this, but it's one of a multi-pronged approach. you wouldn't ask a civvie girl for a blowjob without some prior physical contact, so it's the same thing, just steps being taken to escalate, like slowly boiling a frog.
- warm up to the topic of dating and feel out what her situation is from an indirect angle. she's visiting NY so it's easy to ask about how she likes NYU or NY. Ask about the nightlife which inevitably leads to dating culture and what she thinks of the guys in NY.
- make yourself an empathetic and soulful figure. once you're on the topic of dating or girls / guys in general, maybe she'll open up to you about what she's into and what she's not, tho no need to take that as a red light if you're not her type.
- once on the topic of dating, she might ask about you or you can steer it that way. many ways to take it depending on her and your game, but one way might be to talk about your own heart breaks that will make her unconsciously empathize and root for you, make her see things from your perspective, humanize you and make you a romantic figure, not just an older interesting man she met on her NY adventure.
- be as funny and non-linear as possible. I am terrible at this as my career and personality (and possibly adhd?) tends to make me extremely logical, linear, and serious. before dates or going out, i watch stream of comedy routines on youtube for an hour or two, so I get in the right zone...seeing things from an angle, seeing the irony, humour, and absurdity in situations, instead of analyzing them for a solution or being critical.
- even when I'm on a roll humour wise and making the girl laugh, I make a point to look for rare moments when I can be (or seem) unintentionally vulnerable. for example, we might be joking about dating mishaps or exes and I might laugh a long but suddenly be a little silent or look off into the distance for a split second before forcing myself to laugh along.
- this will make it seem like you are a soulful and vulnerable person, which brings out the motherly and empathetic instincts in girls. it will make you seem a deeper person and make her not want to hurt you.
- I'm realizing I sound like a total sociopath or Dennis from Always Sunny in Philadelphia...just trying to do a brain dump of ideas that may or may not be helpful
- the D.E.N.N.I.S. System if you're curious...
- being a musician and busker is an amazing advantage, especially for girls who like music. at a minimum, it's a great entry way to interact and flirt with a ton of girls. and a great topic to talk about and make you look cool, artistic, and soulful. if I had your skills, I'd be chatting and flirting with girls all the time, even if nothing came from it...which means you have nothing to lose...which means you're confident and creates a low pressure situation for girls to enjoy and hang out with you.
- I definitely would've taken her for drinks, not a cafe. maybe a classy wine bar or jazzy place. and get lost in conversation. no downside in lowered inhibitions, not just for possible sex, but for better conversation. Even if I don't bang a girl on a date, I enjoy the flirting and feeling the warmth of her body heat near me...I enjoy the sexual tension, even if sadly only in my mind sometimes.
ok that was almost a short story...hope it helps. very open to criticism and improvements as I'm still actively dating civilians and picking up girls half my age...or trying to.
Verbose as this is, it is on point. OP needs the magic word.. patience.. Patience and opportunity. The door will open, however if the door gets kicked in, it rattles people. He kicked the door in. He basically said here is dinner, now i want to get in your pants. She was insulted. This isn't a by the hour woman, and therein lies the lack of patience. There is no romance in the hobby business. Some of these guys think it is, they are simply simps getting played by a pro. This was a classy young woman, sharing a NYC experience with an older man, one whim she thought was above that. That is why she was there in the first place.
Now if it was me, I would have sprung for a high end hotel room with a piano bar. Something like the old Booby short setup at the Carlyle. After drinks, and some music, I might have gently asked if she would like to go upstairs for a nightcap. Might have gone differently. Ambiance goes a long way.
There is an interesting gentleman who writes a column about men and women. His name is David D'Angelo. He talks about the power and attraction in relationships, dating and established coupes. Once you lose the attraction, it is difficult to regain it. It might me something you do, something you say, being cheap, blurting things out. Whatever it is, once a woman loses her attraction for you, it is over. She lost her attraction for him, for all the previously stated reasons. The only lesson learned for the OP is what not to do next time.