But where humor is concerned, take your cues from her. Pay attention to the kinds of jokes she tells, and the things she finds funny. If she gets bold enough to tell a naughty joke, it's just her way of showing she can let her hair down, and proving that yes, she acknowledges her own sexuality instead of trying to deny it. NOTE: This is not a cue for you to launch into the story of the preacher and two nuns that accidentally walk into a donkey show.
In American society, it's not unusual for people to be on a medication or two for issues like depression, anxiety, or one of a dozen other mental instabilities. If the lady of your (wet) dreams labors under the weight of a reliance on a prescription, try to be cool about it. If she warns you about signs of her dosage wearing off, pay attention and tread just a bit lightly if you see them. However, if taking her meds includes wrapping a tourniquet around her arm to make her veins stand out and then self-injecting antipsychotic drugs, then you've got a genuine bunny-boiler on your hands. There's only one safe thing to do. Run. Run like the Antichrist himself wants your ass cherry, and all the Hounds of Hell are right behind him, waiting to tear apart whatever he throws them when he's done. Change your phone number too, if you've given it. Pursuit and wooing are one thing, abuse is another. Don't stick around for any, even if she's an H-cup. There are other fish in the sea.
Now, assuming you've been on a successful date, and she has expressed a desire to see you again (You lucky mook!) you've only got one more rule to follow. DON"T FUCK IT UP NOW. It's a lot safer to err on the side of discretion, rather than pushing for things to go farther than she wants, sooner than she would like. If she enjoys spending time with you, she'll want to spend more time around you. It's a beneficial, vicious social circle. People enjoy enjoying themselves. If you need some clues as far as pitching woo without going overboard, try watching the movie The Tao of Steve. Don't live it line for line, but take a few hints.
With any luck, the hints I've given you have gotten you her attention without tripping her creep alarm. It's up to you to handle the rest. Once you reach this point, go do that voodoo that you do. If things go well, you'll be the guy smiling because your voluptuous vixen is going home with you after club-time, instead of the sweaty, jaw-dropped loserboy who bellows over the music, 'Holy shnikeys! Get a load of those sweater-monkeys!'