How do I overcome my lack of relationship experience?

You say you're not specifically hung up on the virginity thing, but many of your examples of disappointing interactions with women seem to fast-forward past the bulk of the encounter to focus on your inability to close on sex at the end ("how does the conversation change from "wow, that's some crazy weather we're having" to "how's about we fuck"?). If you're at some level entering every single encounter with a woman expecting that it might (in one fell swoop) be your first date and first kiss and first love and first intimacy and first sex.. well, that's a lot of pressure on yourself, and on her. I can totally see chickening out of that at the last minute, or standing aside and waving some other guy in. You're doing that rope-climbing thing where you look all the way up at the top of the rope, when you're really just supposed to focus on the next foot you have to climb. For that reason, I really like safetyfork's idea of focusing on incremental low-stakes goals at first, even in the realm of relationships. If you think about the "average" way guys learn this stuff in high-school/college/postcollege, nobody gracefully selects a woman who's the perfect combination of physical attractiveness, intelligence and personality, then woos her in a whirlwind week of perfectly executed dates and beds her that Saturday night. Seems like people just pick someone nearby that they kind of like, then focus on getting into some sort of interaction, THEN focus on getting to hand-holding, and only THEN think about maybe a kiss, etc. What if you put sex (or even making out) off the table altogether for now, and just set yourself the immediate goal of getting a woman one-on-one in some sort of romantic context? Then, when that goes well, maybe try to repeat it with someone else you like, and so forth, and then after a month or so you won't be the guy who's never been on a date or kissed or had sex, you'll be the guy who's been on several dates but has never kissed anyone or had sex. At which point, raise the bar, rinse, repeat.

A few things:Risk aversion has to go. Start taking risks. Not stupid risks or spectacular attention-grabbing moves, but not merely symbolic risks either. You have to learn to evaluate and push through low-grade habitual fears that are pointlessly holding you back from things you want.Whenever you find yourself entertaining http://en.wikipedia.org/wiki/Other beliefs about women, reject these beliefs and whoever fed them to you. Repeat to yourself: women are (only) human. You're just dealing with people. This includes any dating advice you read that's based on a gender-vs-gender model of tricks and manipulation. Even if such things get you laid, you'll have years of toxic thinking to wash out of your head after. Stop thinking of women as prizes go get, things a person deserves, etc. They're people you may or may not manage to connect with. That's it.You're conflating "flirting", "asking out", "having a date", "kissing", "sleeping together", "being someone's boyfriend", "having a relationship", "being in love", etc. These are all different activities, especially in the mind of a 30yo. You're burdening each with all your ill-formed beliefs about the others. This will not serve you well. Treat each event as its own event, that might be all you do with a given person.Swear off the "I'll just hang around and she'll get the idea" strategy. It doesn't work for anyone, men or women. People generally like direct signals, so long as they're delivered with tact. This means flirting. Flirting is just "direct signals" condensed to a subtle and tactful enough level that they're deniable by each party. There are explanations elsewhere, but it's a simple language that's pretty unambiguous once you can hear and speak it.Forget your damn "standards". They're part of your bi-modal self-image, it's pure self-absorption. Get over yourself. You swing between speaking highly of yourself and trash-talking yourself. This is a strategy to avoid reality in favour of fantasy: you're either the king of the world or a gutter wretch. Bad news: you're neither. You're a guy who wants more connection than he's had. So go work on connecting more. That's an activity and you've a clearly-stated desire to to do more of it. Activities happen in reality; standards and judgments (about self and others) happen in your head.When you get around to a part with physical mechanics you don't really know, the phrase you're looking for is "I'm a little new to all this". Everyone's new at some point. Don't overthink it. Just admit it and let her show you what she's into. You'll probably get it wrong a few times anyways (extra reason why your standards don't, at this point, matter much). You can figure out what you're into later.

This is a well thought out question. It's got multiple parts, so I'll take the easiest one. My general M.O. is to hang out with a girl until she gets the idea that I must be interested. So far, that hasn't worked out for me There's a much easier and more effective way. Go to the woman of interest and say, "I'd like to ask you out on a date. Would you like to go with me to [activity] on [date]? I can pick you up at [time]." You don't have to wait for some secret sign that she's interested, or for her to pick up on your subtle clues. Just ask. Sometimes a woman will say no, and that's ok. Sometimes a woman will say yes and that's better than your current results.

As nanojath goes, so goes my nation. I think the single biggest factor in why you aren't getting dates is that you are not asking for them. You hang out with the object of your affections a lot in the hope that... she'll ask you on a date? If it's so big a risk that you can't be expected to take it, why would you expect her to? You're the one that wants the date. That's like being the knight who sees the dragon and gets scareded and hides in the hope that the princess will slay it for him. Okay, gender stereotypes, but that's actually not what I'm talking about. If you display interest and she does notice it, but then you won't express it, it conveys that you are either not really that into her, or are into her but not enough to risk any emotional discomfort for her. Not only is that a turnoff but it can suggest serious problems down the road. I've been thrown together with guys who had this courtship style, who I was not dating, for extended periods of time and their lack of willingness to have difficult conversations extended to more things than just romantic interest. It became very clear over time that if I had decided to help the shy boy out and do the asking, I would have ended up in the kind of relationship where you one day open a cupboard and two years of unpaid bills and a foreclosure notice pour out, because he didn't want to admit he'd lost his job. I also know that this guy broke up with his GF the same way he got together with her: first he didn't know how to ask her out so he sat there like a bump on a log until she figured out he was into her. Then he didn't know how to break up with her so he sat there like a bump on a log until she figured out she wasn't wanted and hadn't been for a while. It must have been extraordinarily painful for her to have been rejected in such a protracted, cruel way; but if this ever crossed his mind, he didn't show it. All he knew was that he was socially awkward and therefore it was her job to deal with it. Maybe my experience is unrepresentative, but consistently, the way a guy expresses romantic interest is the way he'll do everything. I am sure you don't want to be that guy, so start by doing what he didn't.

I have fairly strict standards. I require a woman who is intelligent, interesting, and at least somewhat attractive. My standards are probably too high, but I am unwilling to compromise on them. I'm just not attracted to dumb, dull, or ugly. This makes me wonder if you give people a chance--a chance to get over their nerves or awkwardness and share what's authentically interesting about themselves, and a chance to become attractive to you. You may be setting your sights too high, expecting perfection when you don't have perfection to offer. Imagine a woman saying she has strict standards and would never go out with a man with no experience, or who is still 30 pounds overweight.

Advice I've given before: Have high expectations for who you'll be in a relationship with, but low expectations for who you'll go on a first date with.

Third, if it comes to a situation wherein I'm competing with another guy for a girl's attention, I lose. More accurately, I concede. This has actually happened a couple of times in the last several weeks. I've been hanging out with a girl, and another guy starts showing some interest. The little voice in my head tells me that she's clearly going to be more interested in him, so I pull back, and tip my king. I don't know how to tell the other guy to fuck off, and, more importantly, I don't know how to convince myself that I should tell the other guy to fuck off. You shouldn't tell the other guy to fuck off! Don't do that! That is not an effective way to get a date! This is bizarre and confused and wrong and makes me think that you have watched too many stupid movies! Yes, in movies, men are always getting into fights over women. And the winner is always mysteriously Getting The Girl, as if her love was some sort of boxing trophy that was automatically awarded to the guy who won the fight. In the real world, it doesn't work like that. I mean, if nothing else, imagine how you would feel. Suppose that two friends of yours started fighting with each other over your attention. (Imagine one dude friend of yours saying to another dude friend of yours, "Fuck off, he's mine," and then being like "Okay, Anonymous, now you have to be my friend and stop talking to Steve over there, because I won and he lost!") You'd probably think they were acting like idiots, right? Well, a lot of women feel the same way. In general, this is a good rule of thumb: Women are people just like you, and dating is not fundamentally different from being golf buddies or study partners or part of the same book club or participating in any other human relationship. If you meet some guy and discover he has good taste in books and you want him to join your book club, what do you do? You ask him. You don't go around threatening all of his other literate friends in order to thin out the competition. You don't hang around him nonstop waiting for him to be all spontaneously "OMG I NEED TO BE IN A BOOK CLUB WITH YOU" without you ever mentioning it. You just say "Hey, we've got this book club thing, you should come along sometime," and either he says "yes" or he says "no," and that's all you need to do. Dating is seriously the same way. It's not a prize which the cosmos awards you for exceptional manliness. It's not a boxing trophy. It's really just two human beings who decided to do a thing together because one of them asked and the other one said "yes."

It became very clear over time that if I had decided to help the shy boy out and do the asking, I would have ended up in the kind of relationship where you one day open a cupboard and two years of unpaid bills and a foreclosure notice pour out, because he didn't want to admit he'd lost his job. So, so, so true. This why I won't do the asking for the first date, even though I am perfectly capable of doing so (but second dates and on, I'm more than happy to take action). I've learned it gets me someone who won't go out of his way to take risks for his own happiness/well being. I very much want someone who will actively pursue what is good for him, and by extension, the people he cares about. Say you marry someone and down the line get really sick - you want someone who will get on the phone and harass the doctors for you, not someone who will ignore your situation because he is scared and hopes it'll get better without him engaging in reality.

You've bundled up so many issues into one big lump of anxiety that it is hard to know where to begin. Number one is that if you are feeling anxious or unhappy about something, that's all the reason you need to chat with a therapist. Unless you get head into a happier place, I don't think the rest will follow. Number two is I kind of agree with the person above who pointed out that although you say it's not about the virginity, it comes across pretty clearly that it is indeed about the virginity. There's nothing wrong in my book with visiting a competent and professional sex worker (ideally in a legal setting, as in http://www.reddit.com/r/IAmA/comments/wxn5i/my_name_is_amy_page_and_iama_legal_prostitute_at/ on Reddit; that person says she even gives discounts to first-timers) to get the first time out of the way, and then move on to dealing with all the relationship questions separately. Wear a condom, and just say you had a "one night stand" if you ever need to say anything. As a side-note, though, your use of "hooker" instead of something more neutral like sex worker is kind of like your use of "girls" and your odd emphasis on "high standards" -- taken all together, it isn't exactly a glowing expression of respect for women, you know? If some aspect of this is coming across in person, it might explain some of your problems; a dispassionate outside observer could hopefully see if this is the case and suggest alternative ways of handling things. Which gets me to number three. There have been several FPPs over the years on http://en.wikipedia.org/wiki/Sexual_surrogate, the (controversial) use of intimate contact for therapeutic goals. You don't need that, but you would be an outstanding candidate for a dating surrogacy service -- someone who could work you through various scripts and how-tos for everything from flirting to asking out to being on the date. I'm know I've read about these kinds of dating acting coaches before, and if you could find one it would be money very well spent. But lastly, I'll just say straight up that this stuff is hard. I don't care how many relationships you have had, it is still hard to figure out whether someone likes you, whether or not it is appropriate to ask someone out, and what to do when you get there. I think it's a lot more about being willing to put yourself out there and risk rejection (including setting up situations where things are clear enough -- "Would you like to go on a date with me?" -- that the other person can say yes or no) than it is about having previous experience.