I'm super shy around women. I'm a shy person in general, but more so around girls, I think because I'm more attracted to them than men. Also, there's not many I know that are lesbian or even bi. So, it's hard for me to even find a purpose in being friends because I don't want to fall in that trap of having a huge crush on them and then not getting it returned because I've already gone down that road and it sucks.
At the same time, I know that if I don't start talking to women, I'll never gain the confidence to actually ask one out and feel as comfortable as I do around guys. I just don't know how to get around to even going up to one as a friend. Most of the girls I know met me through someone else in group situations, never one-on-one, and even though I socialize better with guys, my social skills are still really really poor.
I want more women in my life so I can feel more comfortable when/if the opportunity arises for me to possibly have a relationship with a girl. I just don't know how to talk to them without being a total creeper.
Have you thought about trying to meet some women online? Even if you don't think you'd meet up with them in person, maybe it would help you build your conversational skills and it could translate to "real" life.
Volunteering helped me a lot in developing confidence to talk to people. I've done different things and built friendships in a variety of age ranges. You then have common interests and goals -- you have something to DO rather than awkward conversation to make. Then it all kind of translated when meeting guys or girls in social situations.
So, I'd recommend volunteering and just having fun with a group where you (or meeting someone to date) is not the focus.
We've been doing a lot of these awful networking classes lately for my business plan, and I cringe every time we do group excercises or have to build up a dialogue with total strangers... I think most people hate breaking the ice, but with time and practice it gets a little bit less unbearable each time. I wouldn't push yourself if you don't feel comfortable, but maybe going out with a friend or acquaintance would take a little of the pressure off. I must admit it's increasingly difficult now to just meet people outside of work, but it's possible if you stay open to it.
Feeling shy or speaking bashfully is actually incredibly attractive to me, and I'm guessing other people too; it gives a clear indication that your opinion matters to them, and that they like you (perversely)... so there are some plus sides. There's some good conferences at the moment about how introversion is undervalued; I'm not sure if it's entirely relevant but might be worth a look. It's a little lengthy but hope it helps.
It may help to remember that some people have bad days. I usually don't have a problem talking to people but then it doesn't really bother me when I'm given the cold shoulder because I just assume that either they're having a bad day or need some alone time (just as I do at times and appreciate it when others respect that) or they're not worth knowing anyway and I'm glad to have not wasted more time on them.
Beyond that all I can think of to say is watch for signals. If she's reading or working on a computer, if she's sitting on a bus lost in thought as she stares out the window, and especially if she has her arms folded and looking away then don't bother her because you're likely to annoy her or worse.
If she speaks but is short, to the point (even if polite), and looks away a lot then I'd say something like "see you around" (depends on the exact circumstances of course), and also look to see how she reacts the next time she sees me. If she looks away again (even if she puts a polite smile on) then I probably won't bother talking to her again.
OTOH, if she's paying attention to her surroundings and making eye contact then she's likely to respond well to being talked to (and if she doesn't then you probably don't want anything to do with her anyway). Personally I've found women easier to talk to because they're more likely to talk if you seem interested, which is good because she'll reveal a lot about herself without even trying (tip: if she starts off talking trash about someone then know there's a good chance she'll be talking trash about you next and don't give her any ammo as you get away and stay away), though OTOH women tend to be more judgmental than men so it's best to do more listening (making enough noise to seem interested) than talking if you can get away with it.
Also beware of women in groups (that is, close together and obviously eying everyone together) as they tend to be a lot more criticizing of others and less interested in new friends (or whatever), and even if they're friendly to you they're likely to pull you into some drama you don't know anything about and would regret learning about. This doesn't apply to a couple of women with a large group of men, though they might try to hook you up with someone (whether you want to be or not) or be so insecure as to assume you're going to take her man (or the man she wants) or at least cause him to be distracted from her (I stay far away from these women as well). It's generally best to approach a woman by herself (with people around so you don't scare her), IMO, as that's when she's the most likely to be friendly.
Apart from that, making friends out of your usual community can be good because you don't have to worry about the consequences of not getting along well.
If it doesn't work, you cut them out of your life and that's all there is to it.
I find that compartimentalizing my life and having friends in different areas of my life always works as a risk hedge, the fore, allows me to not feel too pressured to be liked.
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