You need to achieve a lot of things with your conversations. Here I've written a short "cheat sheet" to help you with some lines and what you can do with them in a conversation. Good luck and have fun!

How to get into the fun-zone:

“I need to hear that story…”.

How to start a (preferably fun) topic:

“I’m addicted to poker” or “Guess what I’m addicted to”

“So, you’ve ever played poker before?”--> “It totally reminds me of that one guy who would always go all-in back in high-school”

Variation: “So, you’ve ever played poker before?”--> “There’s a poker tournament coming up, it’s gonna be long and hard to watch, how would you like to be on live TV?” which can go to “I love long and hard things, how about you?” or “I could totally see you on a reality show, you’d be one of the mean girls that fight and spit on each other”

“What turns you off about poker players? What turns you on about them?”

“Speaking of poker, tell me a little bit about what you do to blow off some steam?”

Breaking the rhythm:

“You’d look really hot with black hair” to a blonde. “I just caught you staring at me” it will make you look bold. “Does this mean that…?” Bring attention to things you want to challenge (maybe she's incongruent and you want to call her out)
“So the sex got boring?” When the girl broke up with her boyfriend. “Guess” when she asks some boring question like what your job is. Don’t give an answer right away.