I have, regardless of sexuality, and most of the times I can remember, it went well.
Awkward social thing:
Ever coincidentally walked behind or near a lone woman at night? I have. I always try to make some distance so she's not scared, like, crossing the road and then overtaking so you are neither near nor behind.
Of course the irony is that now she is LESS safe than she was while a normal non-murdery person was "following" her.
Used to happen to me a lot during college years. Never failed to feel awkward.
I can relate to this, a lot. I live in a very safe european country where these crimes are nothing the people are used to. Also, I live on the countryside of that country, far away from the big cities where these things might happen. And on my way home, after dusk, I still notice women looking over their shoulders nervously. I always walk slower than them on purpose (and they're almost running). I'm usually well-dressed (suit), so I don't look like a bum either. Still doesn't make them any less comfortable.
One time, a woman started actually running when my phone started ringing.
You know, I get it, they have a right to be paranoid. But my goodness gracious, nobody can expect me to like being suspected as a possible rapist every time I walk home from the bus station after 20:00. For fucks sake.
No, I've been threatened by mace at least twice just by walking behind different women heading to my car. I mean I can somewhat understand if I was following them, but they came to my side of the road(which I actively tried avoiding being on the same side to not make them feel threatened).
No, I'm not going to try to comfort a distraught person, I might ask from 10 feet away if they need help or something, but fuck getting maced.
http://www.youtube.com/watch?v=_UWm4Yhli3I
This almost happened to me once. In Europe. In broad daylight. I walked up to her, asking for directions, and I see how her right hand is gripping a pepper spray in her purse.
inb4 people demanding pics to see if I'm monobrow-man.