lets break this down
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the girls are friendly and they approach ME.
yup. that's their job
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she really seemed to like me.
thats her job.
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She shared with me very personal details and I got the sense she genuinely thought that I'm a nice guy, and I'm funny.
It's most likely all lies. to make you sympathise and be attracted.
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Instead of giving me a "dance" in the VIP room, she'd just sit on my lap and talk to me..
why get paid to dance when you can get paid to talk?
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She said I'm the only customer like that

Either lies or because you're the only one dumb enough
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Every time I'd tip her a 50$ her eyes would light, she's so beautiful.
my eyes light up when I get free money. even more so when i still have clothes on.
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One time she told me she wanted to kiss me..
Lies
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Although she never went through with it

See.
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she recently got in trouble with the law and has some steep court fees.. I'm thinking about paying them for her and wondering if she'd finally fall in love with me if I did.
Words fail me
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Yet another side of me is screaming "DON'T"..
Finally something sensible.
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Part of me knows the strip club is a HORRIBLE investment
By definition an investment requires returns. You are paying for a service. Unless you've actually bought a percentage of the ownership. In which case it seems a fairly good investment. Especially with guys like you around.
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and my chances of success are extremely low.
I'd say non-existent
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And that part has been winning out as I haven't been to it in three weeks..
Whey. Another sensible move.
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feel free to offer up some useful tips for strip club game in general, I'm badly in need.
Strip club game is not a thing. It's not possible. You can't chat up someone you are paying to see her boobs. In the same way you can't chat up the groceries you just bought.
Your best option is to ask if she does escort work or if she has considered prostitution.