Where to begin... I have intimacy issues. I have trust issues. I have self-worth and self-image issues. Overall, I have a lot of problems up in my head that lead to me not really being able to follow along with any of the non-verbal cues that come up during interactions with women - I either start getting messages that aren't actually there or I am totally oblivious to very strong signals pointed in my direction (I've had friends at bars admonish me for being so frustrated with not being able to maintain conversations with women because some girl I tried to chat with that very night, "Was totally into you!" they tell me, and I just thought she was bored out of her mind so I walked away). Not only do I miss the cues, making it dang near impossible for me to initiate casual dating, but my lack of confidence tends to ruin things even if I happen to find someone that can look beyond my awkward, hesitant and shy responses to... well, anything involved in social interaction with someone I'm attracted to. When the dating starts I have only thoughts of how short I must be falling by comparison to every other person the girl's been with prior to me. That affects the dating, but when it gets to sex... owf. Then it gets very bad. The main staple of my self image issues center around, of course, inadequacy both personal and physical. Sigh... I've "powered through" the fears and anxiety I have before... but it's always lead to an encounter which, while the women have said they enjoyed it, seemed like a lacking experience for me. Like if they could've had the same thing with someone else with... some slight modifications to their physicality... it would've been better - they would've preferred it and they know it (is what goes through my head).
I want to do something PROACTIVE and SAFE. I can be proactive and I've tried to be - "putting myself out there", if you will. It's... horrible. I hate it - which is why I say it's proactive but not safe. I feel uncomfortable the whole time and the questions that I want to ask my closest friends about my experiences when I'm putting myself out there draw the most horrible, shaming looks from them (at least, that's what I see...). They don't understand how it could be that I don't understand how romantic or intimate or whatever you want to call it relationships begin and progress, but I don't. They can't help me... it just makes me feel worse to talk about it.
Not being pro-active hurts as well. I'm lonely. I seem to have been able to maintain the same libido I've had since I was 13 (I'm nearly 30 now) and I have only myself to help myself with that. That takes care of the physical side of things... but I'm still just lonely. And I feel like I'm doing everything all wrong all the time to fix it.
Is there anyone in this town that can help me? Is there a place I can go with the safety and protection of anonymity (at least relative anonymity - if a therapist needs to know me, so be it) to get these questions answered? I'm on a limited budget and I've tried general counselling that I can get assistance with, but the people there are grad students that don't have a special insight into issues of feeling sexually inadequate. I've been briefly to a "real" therapist, but, again, I feel like I need someone specializing in being able to answer the questions I have about... hell, what's even socially acceptable behavior for me... How aggressive am I actually supposed to be with someone I'm interested in? When a woman says "No", it means, "No"... then, why have I had women that have said "No" then been angry and thought I didn't like them because I DIDN'T try anything? Are there any studies out there, surveys, some kind of scientific/sociological data on when size does start to matter? No one has been able to answer these kinds of questions for me... and I'm getting tired of trying. But I don't want to give up. So here's a question on a website... Shot in the dark. Fingers crossed. Help. Please.
Before tackling the matter of how to talk to women, it may be beneficial for you to focus on dealing with your issues involving your own self-worth and self-image. I'm sure you've heard this before, but you must learn to love yourself before your can truly love somebody else. With that said, I think you are heading in the right direction by asking for references for further help in these departments.
Speaking with a therapist may seem a bit intrusive, and even costly, but at the end of the day each session is an investment in creating a better future for yourself. Keep in mind that a certified psychotherapist is required to keep you information confidential, and they are generally trained to work with all kinds of people without judgment. So what do you have to lose?
Also keep in mind that it will probably take numerous sessions to make significant progress. Learning how to love yourself most likely will not happen overnight. Again, this is an investment in your future, and spending a few hours in therapy will probably be worth it in the long run. Assuming you live in the Santa Cruz area, I am going to refer you to Tim Hartnett, Ph.D., and Melissa Fritchle, LMFT. You may feel more comfortable speaking with one over the other based on their specialties, background, and/or gender, and it may also be a good idea to try speaking with each of them to see who is a better fit for you.
One quick point I want to make in terms of approaching women: there is not one universal piece of advice I could give you in terms of what women want. All women are different. To most, no means no, but sometimes this changes depending on the context. And size might be a deal-breaker for some, while to others it is the last thing on their minds. What is important is that you develop the self-confidence to overcome your fear of what other people think of you, which in turn may allow you to begin developing meaningful relationships.