Cupra, I understand you entirely. You want to have a legit reason to step into her space and interupt her ritual; you are now cutting into her personal time. More importantly, you'd like to have something to say that justified this interruption. I'm a little more sensitive to your concern than noob, so Ill recommend a few things, but to be level with you, i wouldnt try and talk to a jogging woman with headphones. In my experience, the best results are garned when no one is in a rush; moments of leisure, and no imminency to complete a task. For example, i'd rather talk to that same woman if she was simply resting in a park instead of running through it.
That said, I have talked to a female who had on headphones. She was sitting next to me on a bus, listening to her music, staring out the window. I realized I might not have had another chance to talk to her, so i simply tapped on her shoulder, she took out her headphones, I asked for her name, she gave me it, I gave her mine. We kicked it briefly.
In your case, jogging females engulfed in their music, sweating in the hot sun, reaching to meet that mile and a half--- you've got to have balls of steel.
Track 101, breath conservation is top priority. I doubt a jogging woman would be willing to talk with you, expending unneccessary energy. Thats what she goes to the bar, friend's party, club, or social gathering for. When she goes jogging, she isnt looking for someone to talk to.