I had an Irish friend who was a master at conversation. He once explained to me his technique. He would open a set, say something outrageous or weird and follow it with a weird question. One example: He'd walk up and say "Have you ever noticed that squirrels are picky about which nuts they take and which nuts they leave behind? What is your favorite type of nut?" I once went out with him and he asked every person he passed on the street "What is your favorite type of nut?" and then after they answered he would explain the personality types of people based on the type of nuts they liked. His reasoning was simple. It knocked people out of their normal headspace and after he walked away (he'd keep the first conversation quick) they'd be wondering in their heads "what is the deal with that guy". It made him stand out. He was a combination of natural and well practiced and it worked incredibly well for him. Everyone, guy and girl alike, wanted to keep talking to him. He could keep a conversation going.

I try the scatter-gun approach and it has limited success. After the first 2 minutes of opening, when the "where are you from, what do you do" is out of the way I start fishing for topics that will engage. It is good to have a stable of interesting questions like: "If you could be any super villian from movies or books which would you be and why" or "If you could be a professional athlete in any sport in the olympics which would you choose?" It can be hard to work these into a natural conversation so I try and go on situational awareness - try and pick a topic related to the conversation thus far. The idea is to force the target to be creative with their answers. This gives you the opportunity to neg them ("Why would you want to be a swimmer ... that is a boring sport, just going backward and forward in a line") or qualify them ("I think being a snowboard freestyle athlete would be awesome" + touch on the arm).

I find that one of two things happen - one the girl gives me nothing. She isn't interested in my stupid leading questions or she gives boring answers. I keep changing the topic in that case until 5 minutes or so have passed and if nothing I try grabs then I exit. The other case is she engages with a particular topic. Sometimes they will get really into it and show some surprising creativity. Usually this creates an engaging conversation that will last up to 15 minutes.

I've gotten pretty good at this now. About 1/4 of the conversations I initiate end up with the set or the girl engaged. If you pick the subject well you can use it to lead into kino quite easily, especially if she is excited by the topic. But after about 15 minutes it starts to feel artificial so that is where I get a bit stuck. At that point I need to get the girl less interested in the conversation and more interested in me.

But if your trouble is even getting a conversation started then I hope this helps.