I find a lot of people are scared to run outside at night, and for a good reason: there are homeless people, gang members, cars can't see you, drunk people, and whatever else. I can see it especially being a problem for women.
What I find is when I am hammering the pace, say I do a 5 mile tempo run at 5:10-5:20/mi, NOBODY messes with you. I've done this downtown, in neighborhoods, around bars, and when you are flying that fast more people cheer you on or look at you with jaw dropped instead of harassing you.
I guess what I am saying is, I find that when I do a hard run during night, nobody messes with me, but if I am just slogging 9 minute miles then I look less serious and am more apt to get harassed in bad areas.
Any thoughts?