After a chance meeting with his high school sweetheart reminds him he?s not who he aspired to be, a responsible 29-year-old risks his healthy relationship and stable career to live the life he dreamt of.

For the new one: I dig it more, but it still feels a little conflict-free. My first thought was "why doesn't he just explain to his girlfriend that he'd like to be more adventurous or whatever, and give her a chance to do it WITH him, if it's such a healthy relationship?" My second thought was "what kind of life did he dream of that would end his current healthy relationship? Does he want to be a crime boss? Is she a huge dullard who hates fun?" It seems like the kind of story that would evaporate if anyone simply communicated.

>>>>live the life he dreamt of.

Which is? What's the Biggest Dream of his life he has foregone?? And why? He didn't have the guts to pursue it?? Or does he blame his love interest??

This sounds like conflict, but isn't

Unless you can give us a good reason why he should stay with his current 'steady girlfriend' you are not going to have dramatic tension.