Playing With Pain is a serious romantic comedy about a man so at-odds with the world that he drives away the women that love him. Kevin Milton is a man of no compromise. A prosecutor for the city of New York, he rails against all the evils about him; but, more importantly, he rails against all the evils, stupidities, frailties, wrongdoings and shortcomings of mankind. His problem is that he is a man of integrity - which is admirable, of course, but which can also drive people nuts. Indeed, Jessica - his wife - has divorced him. And Cleo - his girlfriend - is threatening to walk out on him. In the background is Harold - a co-worker - who has designs on Cleo. Cleo, however, things Harold is a legume. Cleo tries to get Kevin to take it easy. He rescued her, after all, both literally and spiritually - and she wants him to be happy. But she is running out of energy. And then Jessica pops in for a visit - to discuss a minor operation that their daughter must have - and things heat up. Jessica's life is now one of ease, she says. And it's also boring. Kevin feels the old love - but can't be ungentlemanly to Cleo. And Harold keeps intruding. Things are ultimately resolved - but not without a measure of pain for everyone. "What will you do with your pain," Jessica asks. "I'm a professional," Kevin answers. "I'll play with it."