It's tough, especially if you've been teased in the past. Just think of things that interest you and start talking about them- That's how I think most good conversations carry on for so long. Say you like soccer...start talking about when you started playing. It can turn into her then talking about what sports she plays. Then it can change into other hobbies you or her like. If you ever feel an awkward silence coming on, just quick throw in a random topic- it usually seems spontaneous and fun going from one thing to something totally unrelated.

I've also found that texting/typing can help ease into conversing with women. Give chat rooms a shot and test your skills on a stranger

What chatroom would you suggest? I don't really know any.

Omegle.

U chat with total strangers and just ask if there a girl or boy and how old they r if there in your age group. I get into really random and fun convos on that site and its easy to cancel a convo and move on.

Something to consider is just elaborating on what you're already doing. People are great at doing that and it leads to lengthy conversations. At work, people say the most insignificant thing, and it ends up leading into a ten minute conversation. In your example, explain why you like the shirt. Does it match her eyes? Does it depict a band/movie/etc. that you like?

I'm a sales person for a technology store and something that every sales person knows is that you must use open-ended questions. No statements allowed (unless providing information) and no questions that can result in a yes/no answer. So when you say that you like her shirt, it provides no opportunity for her to carry on the conversation. Instead, you can say you like her shirt and ask where she got it. If the shirt depicts something, you could ask her to elaborate on it. So if the shirt is a band shirt, ask what her favorite song is by that band, even if you've never heard of the band in your entire life. It shows you're interested and that's what can fuel a conversation.

Ask them if they like garlic bread, thats how I pulled Jade

This killed me

Try it, it works like a charm

if it is anywhere near a meal time... "So what do you think about Mexican"... if a guy i know (hell.. maybe even a random guy!) says that ... he would get a date right then... we would go get us some Mexican food... Im not picky.. I would even be happy with Taco Bell.. (id draw the line at Dell Taco tho... I just dont understand taco combos that come with french fries!)

i know a guy who used to be so shy.. a little socially awkward. He was nice, but had a hard time blending in. He could only come close to blending in with groups of people interested in bicycles or airplanes.. his favorite subjects.. but no girls in those groups.. he knew his problem and hated it. He wanted to find a way out. He decided if he couldn't carry on normal conversations he would try the abnormal.. and he thought being slapped by a girl would be better than having nothing with a girl.. this one is a little tame.. but say the girl said "hey.. I like your shirt".. he would smile and say "hey.. I like your butt... so we have something in commen".. at a swimming pool party he saw a girl with a tatoo partially covered by the girls bikini top.. he actally walked over to her and said he wanted to see the whole tatoo.. he really thought he would get slapped for that one... nope... he got a boob out for that one. He never got slapped. They thought he was funny.. he got included more. He found himself in more conversations.. it took some doing.. and maybe you still dont find him the center of attention in a crowded room... but he has a cute girlfriend and a few other good friends now.. and he still uses situations where he thinks he should be slapped! And that seems to always make people laugh.. (but for this to work I would suggest including a nice smile so they don't take you too serious..)