I have never run with headphones on and don't judge anyone who does, but I have a funny story...
I lived in DC for a few years after I graduated and kept running & competing in some local races, nothing major, a couple cross country races, but mostly road. After a road race another runner approached me and made some small talk about his running group and got around to asking me if I ever wanted to do a workout with them. I ended up meeting up with them for a morning run then a track workout that afternoon. The track workout was short since one of the three guys was injured and couldn't complete it, threw off the entire plan, so the rest of us decided on a run that they knew well (I didn't) that was around 9 miles. I went to my car to change out of my flats and met back up with them to start this crazy 9-miler and both of them had headphones on when I came back. I ran 9 miles with two guys who had headphones & not much of anything was said, which is how I run, by myself, anyway.
I never met up with any of them again and kept running the local races, occasionally seeing them there but never letting them know I would run with them anymore.