You may have to keep trying to pursue completely other paths, building other stats. I know I remember there being something that triggered the option to ask for money when you gave her the ticket, but, again, it's been quite a while since I played through that part and can't for the life of me remember what that trigger is, exactly.
If you're not using a walkthrough, either the step-by-step or even the more middle-of-the-road enhanced hint one, really the best advice I can give is to not get too hyper focused on trying to make something happen, and go try something different if you seem to be hitting a dead end with with someone.
That being said, definitely try to go through the process of seeing the boss of the club, as that opens up a whole lot of new stuff, and lets you get into the club without worrying about money going forwards.