I know it seems like I'm a dweeb but just hear me out for a minute... I never have any luck with girls. Every time I have a conversation with a girl it never gets deep into the convo and things just break down. I never know how to keep it going and it drives me crazy because I've been feeling real... Show More
Most Helpful Girl
First off, it seems like you need a little bit more confidence when talking to girls. Trial and error, man. How are you supposed to learn anything if you're not throwing yourself out there? Girls aren't that scary. At least not nice girls. I find it endearing when a guy really makes an effort to talk to me, even if he seems a bit shy and lost. Coffinspire's idea of what to say to her and talk to her about is the best, use that method when saying hi to her on Facebook. And don't worry, there's nothing wrong with showing a little interest in her at the start. In fact, if you're just a little bit flirtier with her, it'll be easier for you to not get labeled as just a friend or an acquaintance. Girls need that tiny spark almost right off the bat with a guy for her to gain more interest in him. Most girls are really quick when it comes to friendzoning guys, so showing a little bit of interest in the beginning is almost completely harmless. Just don't overdo it. Drop tiny hints here and there, maybe give her a small compliment. It's really easy when you get the hang of it.
As for continuing a conversation, just talk about whatever you feel like. Asking her questions will pretty much get her talking, and it'll give her some space to ask you questions too. If you still reach a dead end, keep it up with the questions simply by playing 20 questions. It might give you some more topics to discuss, like if you ask her what her favorite movie is and she replies with a movie you think is great too, you can talk about how awesome that movie is for a while. Then continue. When I play 20 questions with guys I'm getting to know, we almost never reach the 20th question because we just get so much to talk about that we forget we were even playing.
I hope this helps! Good luck, and remember to keep your head held high :)