So I'm trying to pick up running (OUTSIDE and not on a damn treadmill) now that I've found a partner to run with. I'm noticing a significant amount of pain around my shins and soleus almost as soon as I start running.

This is pretty aggravating as I'm trying to ramp up my cardio and I've found something I might enjoy. I normally HATE running on a treadmill and can barely do it for more than five minutes before I'm utterly bored. The first time I ran with this girl (about a week ago), we ran for a full hour and it wasn't nearly as bad as those five minutes on a treadmill.

Sounds like shin splints. Google it and see if those are the symptoms you are experiencing. You get shin splints mainly from ramping up your running too quickly, as I routinely do, but poor or inappropriate shoes can contribute.