In the last few years, the Internet has seen a huge backlash of anti-"nice guy" rants. Understandably so: These people have plenty of first-hand accounts of jerks who think that they are nice guys who can't get dates because they're nice. The "nice guys" get indignant, and then the women they blame get indignant, and nobody is happy with the situation.
(Gender note: I am addressing an issue that is culturally represented in a one-directional, heteronormative context. Despite my language conforming to that context, much of this essay can be applied to any shy person.)
With the start of the backlash movement, I had a different reason for being indignant: I had spent most of my younger years single, and wondering why women weren't interested in actual nice guys, who treated them with love and respect. It looked like the backlash was answering the question, "Why do women like assholes?" in a highly defensive manner: By attacking the questioner, and accusing them of having no standing to ask the question. While that attack is justified in some cases, it is utterly undeserved in many other cases, and in no case does it address the question.
This lack of an answer is also understandable: The question itself is fundamentally flawed, though not because of who is asking. I will get to that below, but first I would like to say some words on behalf of actual nice guys.
Contrary to the circulating, captioned photos of spurned males, my "friend zone" experiences had nothing to do with acting like a friend in the hopes of eventually getting sex. I have always deeply valued each of my friendships, and I treat my friends as well as I can because I care about them. Any suggestion of ulterior motives would be slanderously insulting. I didn't know the term "friend zone" in my single years, but if I had, I would have used it to describe an evening of desperately trying to cheer up a woman I loved, while she cried on my shoulder because of how badly her boyfriend had treated her.
Fellow nice guys, I have to be honest here: Winding up in this situation, time and again, was my fault. For several reasons, I was scared to make a move, and every one of those reasons was wrong. You probably share some of these ideas, so let's look at them. (Anti-"friend zone" people, you need to keep reading, too.)
No. At best, your advances are welcome. At worst, making a move is a mistake, and friends are allowed to make mistakes. They apologize, get over it, and continue the friendship normally. (What you absolutely must not do, if she says no, is to continue to tell her how you feel, how much you want to be with her, and how much it hurts that you're not with her. That will royally screw up your friendship, and, more importantly, it will hurt her. Put on a happy face, especially in front of her. You can cry and write bad poetry at home, and confide your pain to a trusted guy friend. Just don't make your pain her problem.)
No. If you have a real friendship, and she has a brain, then she will know better than this. (If, on the other hand, she's fickle enough to instantly change her mind about your friendship, then, very likely, either she will change it back later, or she's right.) Anti-"friend zone" people: By accusing shy guys in general of using friendship as a weapon to get laid, you are exacerbating the fear of being perceived this way. You are thus making yourself part of the problem. Please ease up a little with the attacks on guys who are already scared to speak their hearts.
Wrong. This thinking is the result of a vicious cycle, in which fear of rejection, plus one or two actual rejections, leads to never making a move, which leads to extended loneliness, which leads to the feeling that nobody has ever been interested, which leads to the feeling that nobody ever will be interested. This thinking is also the result of failure to notice or understand the subtle signals that women give when they are interested. (If neither you nor she is giving overt signals, you will suffer The Problem of Lesbian Sheep.) I know that these thoughts were wrong, because I sometimes realized, months or years later, that I had missed a signal that should have been blatant, just because I was so sure that women weren't interested in me. (If you believe in creationism, you will find ways to dismiss or ignore the fossil record and radiometric dating. If you believe you are unattractive, you will find ways to dismiss or ignore evidence of attraction. It's the same mechanism (confirmation bias) either way.)
Also, it's possible that you are in fact off-putting. Ask your friends who have some social clue to tell you this honestly. Ask them whether you need a haircut, better clothes, more showers, or better oral hygiene. Then don't resist their suggestions; let them help you.
Well, yeah. Rejection hurts like hell. But: 1. That's a terrible reason not to try. And 2. There's something you can do about it.
Regarding the first point: Loneliness hurts too. And sure, rejection hurts more. But invoke a little felicific calculus here, which is to say, use your whole brain, not just your amygdalae. Rejection is only a risk of trying, whereas loneliness is a certain result of not trying. The pain from rejection ends, usually in a matter of months. The pain from loneliness just goes on and on. If you refuse to take a chance, based only on your fear of immediate pain, then you don't help future-you, and you don't help probable-you. You just let worst-case-right-now-you hide from one crappy thing behind another crappy thing. And once the judgment includes the value of the reward if she is into you, then it becomes insane not to try.
Regarding the second point: The longer you hide your feelings, the worse it will be. You will keep building up this love-that-could-be in your mind, and you will like/want/love this person so badly that the idea of rejection keeps getting scarier and more painful. Do yourself the biggest fucking favor in the world, and get it off your chest quickly! It'll be easier (not easy!) because you'll have less at stake. If you get rejected, it won't be as heartbreaking as if you had waited, and you will move on faster. If she returns your interest, then you won't have wasted time, or lost your opportunity entirely. (It happens!) So take a deep breath and do it. Just get it out there.
Also, in general, you need practice getting rejected. It sounds weird, but the things that scare us become less scary with familiarity. If fear of rejection is a huge hurdle, one of the best things you can do for yourself is to find low stakes situations in which to respectfully ask people out with the expectation of getting rejected. Practice it. Turns out, it's not really as bad as it was at first. Loosen the hold that fear has over you, and it won't stand in the way of your love life.
Obviously, this isn't quite the same context as an established friendship, but it does come up, and is a very expensive mistake. See, there's a problem: You've been lied to. By books, by Hollywood, by every love story you've ever heard, and by the stealth puritanism that still infects society with its gangrenous touch even while we lie to ourselves about how much more free and daring we are than our grandparents were. The lie is that two people get to know each other, then fall in love, then have sex. That's it. And while most of our acquaintances learned better in high school or earlier, some of us read too many stories, saw too many romantic comedies, and got exposed to too much subtly sex-negative influence... And we got suckered. The fact is that most people decide very quickly whether to sleep with each other. And if they keep sleeping together and spending time together, then they can build up the combination of shared experience and sexually induced dopamine dependency that leads to the condition called "being in love".
That leads us back to the question of why all these nice, smart, cool women are sleeping with all these scumbags who treat them poorly... And also, incidentally, to the question of why lots of nice, smart, cool men are besotted with women who treat them like dirt. It's not about judgment at all! Judgment doesn't come before sex. (It often doesn't even come before marriage.) People don't sleep with someone because they think the world of them. Just the reverse: The more they sleep together, the more they like them. (Thus we arrive at the real issue with the question, "Why do women like assholes?" It's not a property of women; it's a property of people.)
If this is a problem for you (just like it was for me), it's because your paradigm doesn't reflect reality, and your best bet is to change it. You can fight biology by trying to create love first, and you might get lucky (so to speak), but you probably won't. The good news is that you don't have to abandon your own standards; you can still seek a worthy mate on your terms. You just have to recognize that, no matter how awesome, or pretty, or smart, or nice she is, her standards probably aren't what you think they are. And you have to accept that this says nothing about her.
When I was in college, the collected wisdom of the Internet, on this subject, consisted of "be confident" and "be yourself". I didn't know which one to pick. But nowadays, I'll bet this is just you being lazy and not doing your homework. There is lots of good advice out there, and if you do enough research, you'll learn. I'll put out a few tips here, but you should certainly look for advice from someone better qualified than I. So here goes: Compliment her. Tell her what you like about her. Give her a bit of time to absorb that. When you ask her out, make it a specific suggestion: Invite her to have coffee, or dinner and a movie. At dinner, food fills otherwise awkward silences. Then the movie provides a great chance to hold hands. Have you ever heard an old geezer saying that they know what holding hands leads to? They're right. Holding hands now leads to holding hands later, which leads to gentle caresses of the hands, then the arms, then the face. If you still can't tell whether she wants you to kiss her, feel free to ask permission. If you're feeling too worried and shy, some stages of this process can be replaced with a wonderful line that a friend of mine used on another friend: "Would you be offended if I made a move on you?" It's deferential and disarmingly shy, but still gets the point across. (This was before I met them, but I attended their handfasting in 2000, and hope they don't mind the shout-out.)
Almost every guy thinks they're the nice guy. Maybe you are, and maybe you just think you are. If your main reason for believing that you're a nice guy is that you often think, "I would never treat her that way," then you are just a "nice guy". Treating someone well is more about what you do than what you don't do. And don't bother saying, "I would do anything for her." Everyone feels that way in love. But that statement merely expresses a feeling, not a fact. I've seen a guy passionately declare, "I would do anything for her," then flatly refuse to go shopping with her. Treating people well takes effort, humility, self-control, self-awareness, communication skills, forgiveness, the ability to compromise, the ability to lose graciously, the ability to win graciously, the will to take responsibility for your mistakes, and the drive to change into a better person. If you don't want to be the next asshole who leaves her crying on some other poor schmuck's shoulder, then you need to work on these things. Practice them with your friends, with strangers, and with your enemies. Get good at them, and you'll be ready to shed the quotation marks.
That's a loaded phrase. As a society, we're working on getting past the misogynist (and sex-negative) idea that there's something wrong with a woman making the first move. But there's a long road ahead of us. Some of you women may be suffering from that delusion, in which case, I hope that you can make use of my advice above.
Alternately, if you think that someone you like might be interested but too shy, tell them to read this essay and get back to you.
And who am I to be telling you all this? Just a shy, dorky guy who survived tons of stupid mistakes, is now blissfully engaged (edit: married), and has the benefit of lots of hindsight. For lack of being able to tell all this to my eighteen-year-old self, I'll settle for telling you. If you're half as hopeless as I was, you'll need it.
Good luck and best wishes,