This girl I know said that she was on the verge of breaking up with her boyfriend but doesn't have the courage to do so.. they've been together for 5 years, she said the feeling is no longer there but she's afraid she'll miss the relationship. How do I "push" her to the finally break up with him?

As stupid as this sounds, this is what i've done for the longest time. I've always supported them. Try and help her make things work (well make it seem like your trying to) She'll tell you all the problems, give her a guys perspective. When she mentions things, "My boyfriend is talking to other girls" Tell her that its not right that he is doing that to her, and explain that she has to call him out. What you want to do is make it look like your trying to help her out but you really want to make things worst.

This might sound stupid but i cant even count how many times i've stolen guys girlfriends with this same method.

Neg Support

By using the "Straw-man" technique.

Basically if you talk about how awesome her BF is and exaggerate it to impossible proportions and talk about how they are destined to be together forever, and she will never have a need to experience anything else, this will cause her to re-evaluate her BF in YOUR TERMS... and be disappointed.

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They call me the cat whisperer, cause I know exactly what the pussy needs.

All good tips. Personally, I try to tool the guy out. It doesn't take long to find something out about a person that you can just rip into mercilessly and completely trash their life to their girlfriend.

"Oh, he drives a Jetta? My little sister drives one of those too."
"So he works at Papa John's? Does he smell like pepperonni when he comes home?"
"He's 5'6" eh? Is his weenie also little just like the rest of him?"
"Let me guess, he wears No Fear hats, Tapout shirts, and runs around yelling 'EXTREME!'"

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“Nothing is impossible, the word itself says 'I'm possible'!” ~Audrey Hepburn

wouldn't that make the girl get all defensive or even offended? from what she told me the guy doesn't pay attention to her anymore and has too many different future plans than her (he wants no kids, she wants kids, etc). She's very open towards my approach and said she feels a deep connection with me but then again I've only been working on her for 2 months so it's probably not enough to make her fully trust me yet..

I think in this case the girl wants to end the relationship. If you want to meet hundreds of women do not touch it. You can only imply to something the girl likes much more. Be indirect, because you want to do it unnoticeably.

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You should know exactly where the girl is and reaction of the girl. When the reaction is positive, then you should talk and approach immediately. Women value strength and similarity. If you wait then it changes the relationship even in the future.