First off, I was raised in a very liberal family. My mother deliberately made a point from early on that “love and sex are not the same”, a theme she thought was tremendously important to avoid the phenomena she witnessed where a girl would lose her virginity to a boyfriend, and then stick around for years longer than she should have because “she loved him” – when really she simply was not able to accept that she could have sex, even enjoy it, but not be in love with that person. That losing her virginity without “love” being the reason did not make her a “bad girl.” And indeed, when I did lose my virginity, it was unremarkable – with a boyfriend I was attracted to but certainly had no illusions of being in love with, the sex itself was “eh” at best, and when we broke up a very short time later, I was “upset” for a few weeks but later acknowledged I really wasn’t all that put out by it. (And, foreshadowing my future feelings, my biggest concern was this feeling that others held where breaking up meant you no longer contacted each other – I couldn’t see why we could not continue to be friends.)
The second thing that helped a great deal was that I didn’t have a circle of female friends in high school. I had a few friends (who happened to be female) in the beginning, and later a circle that was mostly guys. Now, I don’t mean to knock girl friends in the least, but I think it is not a surprising thing to many people to realize that girls, as a group especially, are much harder on other girls, and that many of the sex-negative judgments made on girls (i.e. calling someone a slut – and that’s bad, right?) are made by other girls. Looking back on it, I realize that it was helpful to me to be free of that sort of bias when forming my views on sexuality.
Having the viewpoint of guys clearly on display was also very helpful. While I was always a very flirtatious person, I could be a bit shy. Hearing one of my friends explain to me that guys work “a numbers game” was illuminating (if they use that same stupid line with 100 girls and it works on even 1, what have they lost?) and ultimately inspiring. After all, what did I really lose by approaching someone I liked? In fact it’s actually much *easier* to approach a stranger, because there is nothing to lose. You certainly can’t jeopardize a friendship is none exists! The worst case scenario is, nothing comes of it, you make someone feel good (getting a compliment is always an ego boost!) and you both walk away, hopefully with a smile. Is that so bad?
Now if you are a straight woman, this is even easier – guys in general are always THRILLED to have a woman approach them. It’s really hard to go wrong! As long as you approach it with the right expectations, i.e. you are happy to just say something nice and walk away, you have a pretty fine shot of walking away with a whole lot more. Confidence is sexy! (Of course, I will admit I find it a great deal harder to approach women on the street…but that is what OKCupid is for!)
Now, many of the people you meet this way will be great fun, maybe a very good casual-sex fling, but not end up being a deep connection with you. And that is okay! Some of them may end up surprising you, and becoming closer friends than you might have expected, or alternately just someone that you have one random, wonderful conversation with and maybe never even speak to again. All of these types of interaction can be worthwhile, and by being open to them you will bring a great energy into your life.
Positive sexuality. It’s easier than you think!