There is a pattern of behaviour in some men that is very self-defeating. A man who suffers from it finds it very difficult to establish a healthy, primary relationship with a woman. It is Nice Guy Syndrome. Men who suffer from Nice Guy Syndrome will probably have lots of women friends, but rarely have a physical relationship with any of them. He may be a very good listener, and perhaps articulate and expressive in how he talks. He may make a women feel, "At last I have found a man who can listen!". Or perhaps, "Wonderful, this a man who can express his feelings!".
However, there is something missing. Even though a woman may sense that the man is attracted to her, as she gets to know him, she comes to realise that she does not want to be anything other than friends with him. She may at ease with this, or she may wonder, "What is wrong with me? Finally a find a decent man and I just don't feel about him the way I want to!". (The woman may start to wonder whether she is one of those "Women Who Love Too Much". However, this is unlikely as women with that pattern usually get very uncomfortable around the type of positive attention they would get from a Nice Guy). How this dynamic resolves itself depends on how patient either of them are with each other. However, it rarely resolves itself by them entering into a primary relationship.
What is missing?
What is it that is missing? Nice Guys are kind, reliable, safe and dependable. Isn't that what women are looking for in a mate? Well, yes, but... That is not all they are looking for. Women are also looking for a certain amount of strength and confidence in potential mates. A woman friend of a Nice Guy will often be aware of what a hard time he has 'finding the right woman'. She will probably get to hear lots of stories about it! If not, she will sense it from his demeanour. That lack in the Nice Guy can easily come across as 'neediness' and general lack of confidence that puts women off the Nice Guy for anything outside of friendship. His 'openness' with her may also mean that she gets to hear his feelings of concern or anxiety about aspects of his life and this can sound like 'insecurity'.
In essence Nice Guy Syndrome is when a man has got locked into the 'soft' side of his nature and has somewhat disowned the 'harder' aspects of his male energy. This is understandable in that many men are trying to redefine maleness and what that is about. In order to get a handle on something sometimes we need to let the pendulum swing too far the other way. Men exploring their soft side sometimes find it difficult to find their way back to a balance state and reclaim other aspects of themselves.
The Nice Guy will often be open to self-development and have little resistance to looking at their issues and improving themselves. However, ironically his self-development tends to be focussed on areas that don't really help him find a mate. He may do a course on listening skills (when he is already a good listener), or in communication skills (when he is already fairly articulate) or he may do a course in the arts, meditation, yoga, interpersonal psychology, or whatever. These are all very good and useful things, but do not really touch on the issue of improving his love life.
The real need is for balance
What the Nice Guy most needs is balance. He needs to develop those 'hard' qualities that counterbalance his well-developed soft qualities. Those hard qualities are things like confidence, boldness, assertiveness and the like. What he needs is to get into some kind of rugged sport, martial art, assertiveness training, or something along those lines. Even things like jogging or running can help shift him out of his 'soft' mode. Maybe he could get into drumming, or working with clay, or doing sculpture, or some other kind of art that has a strong physical aspect where he expresses himself in a dynamic way. Or, he could pick up a guitar and play some heavy rock, or power blues, rather than too much 'sensitive' stuff. Whatever else he does, he needs to reclaim the full range of his masculinity if he wants to be healthy and balanced.
A curios thing about Nice Guys and the women who are friends with them is that they very rarely fight about anything (or if they do it is rather petulant). At least, it will not usually not be in an upfront way. A Nice Guy may go off in a huff, or break off contact for a while, if he does not get what he wants. If he is attracted to her he may tell himself "I'll show her that I don't really want anything from her other than friendship" and grin and bear it. However, he forgets that women are natural experts at picking up what is going on behind the scenes and she knows only too well that he is kidding himself. That does not exactly engender the kind of trust and respect that a woman needs to feel for her mate. Yes, she trusts the Nice Guy not to attack her but there are other kinds of trust that she needs to feel.
Can the Nice Guy be trusted to stand up to a woman when that is what she needs? Is he strong enough to contain her anger? A woman once said about a Nice Guy, "I like him, but I could not fight with him". What she meant was is that she could not be sure that he would stand up to her when she needed someone to bounce off. She and the Nice Guy got on fine, but what would happen if she were furious with him and really let fly? Could he handle it, or would he be so hurt and offended by something she would come out with in the heat of the moment that it would destroy the relationship? A woman can only trust the wilder parts of herself with a man that embodies the wilder parts of himself. She has to know that her mate can stand up to her and hold his own when that is what the relationship needs to move forward.
Nice Guys tend to get very conflicting input about maleness and the role of men. They get a constant trickle (or flood) of information about the misbehaviour of men via their women friends. They are also told directly, or by implication, that they are all right as they are 'not like that'. Yet, after hearing so many stories from a woman about the hard time she is having with her current boyfriend, it is the boyfriend and not the Nice Guy she has a physical relationship with. He gets the message, "You are special and different", and the message "You are not good enough for me.", both at the same time. He also gets the message "There is something wrong with men.", and the message, "You are alright." at the same time. Does that imply that he is not a man? It's no wonder that it is confusing to be a Nice Guy!
What is also confusing for a Nice Guy is that he often hears women complaining about men not being 'open' enough. He may take note of this and set out 'improve' himself and be more open. Yet, this backfires too. For while the Nice Guy is 'openly' telling his women friends about the problems in his life he is also labelling himself as a 'loser-in-love' in their eyes. The more 'open' he is and talks about his worries and concerns the more his women friends with see him as a bit insecure. Women don't mind that in friends, and may even enjoy offer advice, help and encouragement, but it does not activate their mating instincts. They may like the man and enjoy getting glimpses into the male world. But, they will try and apply what they learn to the get closer to other men in their lives not to him . Of course, openness is a good thing. The problem is that it has to be counterbalanced by expressing some dynamic outgoing qualities or it can come across as 'weak'.
How can a woman help the Nice Guy in her life?
She can help him by being positively selfish (a very different thing from being negatively selfish). She can help him by encouraging him to develop the kind of qualities that she herself would like to see in him. When a woman talks about her boyfriend to a Nice Guy it is usually to complain. Does she ever tell the Nice Guy what is really good about her boyfriend? No. She won't do that usually. That is because she may know that the Nice Guy is attracted to her and if she tells him what she likes so much about her boyfriend she will, by implication, being saying that is not true about the Nice Guy.
If she were to say, "What I really like about my boyfriend is that he is so confident in himself", this would raise questions in the mind of the Nice Guy. After all if her Nice Guy friend had that quality she would want him, right? However, the effect of this unbalanced communication is that the Nice Guy rarely gets to hear anything positive said about the more assertive type of man. This just reinforces in him the feeling that his raw male energy is not OK and that there is something unredeemably bad or wrong about it. It pushes him further into feeling that he needs to stick with his 'sensitive' side. What Nice Guys need from the women in their lives is positive reinforcement of healthy male behaviour, not constant negative confirmation of unhealthy male behaviour. Yet, the latter is mostly what Nice Guys get from the women in their lives.
Women would do better to look at to how they can reinforce the dynamic male qualities of the Nice Guys. Encourage them to develop balance. Maybe tell them about your ideal mate (sensitive and confident, kind and assertive, gentle and bold, etc). Help him to develop an image of what a healthy man looks like. How can he get there if he doesn't know where he is going?
How can Nice Guys help themselves?
If a Nice Guy wants to reform he could start asking his women friends what they really like about their boyfriend (or their previous boyfriends), especially if he has mostly heard a long series of complaints for a while. This helps break the cycle of the Nice Guy unconsciously supporting her negative views about her boyfriend, and other men of that type (perhaps in the hope that he'll get to win her in the end).
He could ask his women friends what their ideal man is like. This starts to move the relationship into a more positive male/female dynamic. It may have been very positive in other ways (having a fun together as people, mutual support in some areas, etc), but the relationship has not likely been positive and mutually rewarding as far as basic male/female interaction goes. He has not been receiving a positive sense of basic male energy and how to express the more dynamic aspects of that. He needs to elicit responses from women (and take the initiative to get them from women and from other men) that help him gain a sense of what healthy maleness looks like and what it feels like.
He might also want to take his relationships with women less seriously. One look at the Personals columns and seeing how many women are looking for a man with a GSOH (Good Sense of Humour) will quickly prove the point. He needs to keep things light and fun - up to a point - and not avail himself of every chance he gets to bare his soul. Finding ways to gently make fun of himself and make fun of his women friends too can also work wonders. Confidence is usually the number one quality that women look for in a man. It is much easier to come across as confident when you are being playful. There is far less risk and far less to loose. Therefore, the Nice Guys number one priority is to develop and express confidence. There are lots of books on this in any good bookstore. Best to have a look and see what appeals.
A different kind of serious
He also needs to look to other men to help him understand his feelings. A woman knows how it feels to be a woman; not how it feels to be a man. She can help him understand the value of being able to know how he feels and to express those feelings, but she cannot help him much with knowing what those feeling are. As Robert Bly says, "If a man tries to learn how to feel from a woman he goes numb from the neck to the navel". Only other men can really help a man come to terms with his masculine self. He needs to find a wise elder (in books, or in real life), or a friend who can help respect his essential maleness.
If he has drifted into feeling more comfortable with women rather than other men then that is a sign that he is not comfortable with himself. He could look at what he does with the wilder parts of himself and how he relates to them. Are they integrated into his life in healthy ways? If not, then he needs to heal his relationship with those parts of himself. Some of the Men's Movement literature is helpful with that (Robert Bly, Sam Keen et al) and helps create ideas for expressing male energy positively.
What often makes is man into a Nice Guy is when he becomes dismayed by the damage done in the world by male energy when it is unbalanced. Nice Guys are essentially healthy men who are attempting to break out of the traditional male roles. They will have gained many insights about human nature, and especially about women, while on their journey. It is then really a matter of them reclaiming those parts of their male selves they somewhat left behind. They can they be the type of the man the world needs: balanced and healthy men, who are strong, empowered and confident who are also comfortable showing care, openness and sensitivity.