No rules anymore. Y2K wiped them out, along with all of the records at Sallie Mae (all right, that last bit's just wishful thinking). Seriously, I think the only rules you need to follow on your new venture into the dating world are:..
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1. have fun..
2. be yourself..
3. try not to stress about what's right and wrong..
4. order expensive stuff if he's paying..
5. if you want to kiss him or sleep with him, kiss him or sleep with him (with the necessary precautions, of course)..
6. Did I mention have fun?..

You are exempt from all the rules ... you've paid your dues ... make them up as you go along ... and do what feels good for you!..
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Angie..
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I'm the yin to Carlos' yang.....

Good stuff ScarlettO! Also...if you like some guy and he doesn't like you the same back - don't take it personally and just move on. Life is too short. Just start dating. You'll have to find your own boundaries as you go. No one has the magic answers. I made a few mistakes when I ventured out into the dating world almost 3 years ago. I learned a lot and finally found my wonderful man a year and a half ago. Still learning!..

There is actually a new book I read about last night in Newsweek. Its about sex and the older single girl and dating. I am blanking on the authors name, but I think you could look it up when you pass by a newstand. It is a memoir that is kind of the opposite of the year of magical thinking. It:s about moving forward and dating...
There are no rules. Just have fun. And do what feels right. Try to avoid sleeping with the guy on the first date -- unless you really really want to. And use protection because STDS are a little scarier than the last time you dated...
You might not want to mention that you have not gotten laid in 5 years. Or if so, read first the book Curse of the Singles Table where a girl goes 5 years without sex...