I gave oral herpes to a woman I only briefly dated a while back. I kissed her goodnight and on the way home my lip was tingling. The next time I saw her we both had cold sores. I was horrified, while she thought it was no big deal. I'm not sure how she may have felt later on as she continued getting out breaks though. That was really a freak accident though. When I was younger and more ignorant about cold sores (like many people are) I used to kiss my girlfriends when the out break was still healing. I wouldn't want to kiss anyone today if I had any signs of an outbreak at all, but I think you really have to be at the start of an outbreak in order to pass it on.
If I were you, I would take 500mg of Lysine a few time a week religiously. Don't eat food that will cause your body to become acidic. I also have great luck using DMSO to suppress any out breaks. Just apply it to the area.