Let's face it. Country music is an acquired taste. My iPod had this problem at first, but I was able to get it used to country music by going through the following procedure.
First, start out with stuff that is basically country crossover / easy listening. This will fool your iPod into thinking it's listening to something else. Patsy Cline's later recordings (after her Nashville producers replaced fiddle and pedal steel with strings and background vocals) might be a good place to start. If your iPod can't take a steady diet of this, then try mixing one or two of these cuts in with other material. Jim Reeves should also be smarmy enough to trick your iPod.
Once your iPod can accept country music at this level, you can move to material more characteristic of the genre. Perhaps early Patsy, or you can also start with late Eddy Arnold and go back in time to the great late-'40s recordings with Little Roy Wiggins on steel. You'll have to do this slowly of course, watching carefully for any signs of protest.
Speaking of "Slowly", it's probably a bit early to intoduce Webb Pierce at this point, but the goal is to get there and beyond. You'll know you've succeeded arrived when you iPod can play people like Ernest Tubb and Molly O'Day without flinching.
On the way, you might try some Willie Nelson; his sound is familiar enough that your iPod might not be scared away. Then you can work back to Willie songs made famous by other artists, like "Night Life" (Ray Price), "Crazy" (Patsy), "Hello Walls" (Faron Young).
And whatever you don't forget Merle Haggard.
I hope this post has been useful. It worked on my wife, too, by the way.