Breaking the ice

Hard to say since ice breakers really depend on situation by situation. Generally, like at a con or party or something of that nature, you can comment on something in your surroundings and just kinda ease in from there. You can also comment on like clothing. " Can I see what your shirt says?", "That's awesome!", "Sweet cosplay, bet that took you a while." yadda yadda yadda something like that I guess. Just find something, anything (that's socially acceptable) to comment on and go from there. You just kinda gotta get really comfortable talking about anything

@cantthinkofabettername: Playful banter is also a good technique, but normally I would agree with you. How ever this on going technique of me insulting girls unintentionally has worked three times now. There's pattern and I can see it. @talamar: That's always a good one.

Wow, thanks for all the advice. I will try out a little of everything suggested and get back to you all with the results. if you guys come up with anything else feel free to post

It's easier to break the ice in front of complete strangers or in a new town. You feel a lot more ease when you know you may never see these people again. I did that this weekend. I had a lot of success on the dance floor.

If you are the outgoing type, just a simple, "Hi, I just wanted to let you know that I really like your (fill in the blank with outfit, shirt, hair, the list goes on)." or some other compliment, but make sure you say Hi at the beginning. Compliments (but only honest ones) are always a good way to start off a conversation with a girl. They will feel flattered and are more likely to talk to you. Then make sure you tell them your name and, depending on how you feel about it, shake their hand. Guys that do that put out a confident air that most girls are attracted to. Obviously you have to read the situation before addressing someone. NEVER, I repeat NEVER approach a girl and try to chat them up when they are on their phone. I have seen guys do that, and honestly you will just piss the girl off. Be courteous, to. Also, I wouldn't do what @Nerdalous suggests. I would never want to be involved with someone where the first thing that comes out of their mouth is an insult. Normally the girls that are attracted to guys like that have self esteem issues and are clingy... So unless you are into that, I wouldn't try. Well, if you are not an extremely outgoing person, breaking the ice can be a bit difficult (I've never had a problem in that category, but I know others that do). If the above sounds like it would be difficult for you, I suggest the following. If you have a friend that is outgoing, tag along with them and ask them to help you meet people. This is best done at cons or other places that are not just random (such as a bar scene). They then do the above and then introduce you to the person, too, and eventually start to drop out of the conversation. If things seem to be going well, they should excuse themselves to do something else (get a drink, go talk to someone else, etc). I hope this is of some help :)

I have a hard time going up to girls because most of the time they travel in large groups. I'm too afraid of making a fool of myself in front of 5 girls let alone 1! Any advice on what to do in a situation like that?

For "breaking the ice", I suggest just going up to them and triggering that flag. Once it's triggered, you'll be forced to fill up those dialog boxes. Even if it's an awkward conversation, it'll leave an impression on your target, and if they don't like you because you're not a "smooth talking Mr. Confidence-Ego", they're probably not a possible love interests. I'm not sure if my method is sound, but for me, it is sufficient; but then again, I don't mind having only a few people in my social circle. <br/><br/> This may only work for people like me, though. I'm pretty shy and think a lot. So the more I think the harder it is. I don't think well on my feet, either. So, either I attack with reckless abandon, or just think about what effect various conversations could have. Reality > Theory

I agree with Alexis, a greeting followed by a compliment is a very good start. Try not to immerse yourself into their life right away. (example: asking tons of questions about them or ranting about all your interests in matter of minutes.) That will come off as creepy. Let the conversation flow on topic and take things day by day. But try to avoid a creepy zone if you can. First impressions make a big difference between a new friend, a blacklist or possibly love~

Alexis Lynn, whatcha think of this one? "Hi, I just wanted to let you know that I really like your shoelaces." Now there's an awkward moment of silence, what should he do now? if he should keep the questions to the there and now? "I'm a gamer, Otaku and awesome dude, wanna go somewhere we can talk?" Don't just give a first line to the guy that's the easiest, the hard-part is what comes after :P