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My friend is 26 and, when we hang out, he typically enjoys looking at nice girls and he hopes to know them. He's never been in a relationship though, and he's very shy with girls. In the past, he's been rejected by two girls but he's now over it.

Sometimes, when he makes me notice some girl he likes, I propose to be his wingman or, other times, I try to push him a little bit. He then becomes scared as hell and there's no way to get him to move towards the girls, so I stop after a bit. I've picked up conversations with random girls with him being at my side, in order to show him that they won't laugh at you and tell anyone to come and see.

He's now also starting to convince himself that all girls have a bad attitude and only want to deceive the males to get attentions, and this really bothers me.

I'm friends with him, and I can see that he strongly feels the need for a relationship, but I haven't been able to help him and I feel that if I keep pushing him I may risk breaking the friendship.

How can I help him overcome this social difficulty without risking our friendship?

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    This question could easily be re-opened, but it should focus on whether or not the goal is to talk to the friend or help the friend interact with women. – Upper_Case Jul 17 '18 at 17:08
  • @Upper_Case the goal is to help my friend overcome this social difficulty, whether it is by talking to him or by helping him in some other way. Sorry if this wasn't clear. – Hopf Jul 17 '18 at 18:10
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    I would suggest your friend come to this website and search some of the existing questions or ask "how can I approach females, usually when i do X they are Y" or whatever – aaaaaa Jul 18 '18 at 1:07
  • Is your friend very shy generally, or is this specific to women for him? – Upper_Case Jul 18 '18 at 14:48
  • @Upper_Case basically just with women – Hopf Jul 18 '18 at 20:16
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There's no general-case way to answer this question because your friend's aversion could be caused by any number of things, alone or together. Specific advice might be different if he's merely shy compared with, say, having some sort of social neurosis. Additionally, we can't really gauge how receptive he'll be to any sort of help from you.

I think that it will be important to talk to your friend, openly and honestly, about what he wants, why he's averse, and whether or not he's interested in overcoming obstacles to getting what he wants. He may not be, and you can't make him. And even if he is, it might feel too intense to him to approach strangers with a wingman right away.

However, I was very shy when younger (not just with women), and here are some ideas that helped me, as well as some conclusions that I reached in retrospect.

1. Sometimes things won't go well. But sometimes they will.

This is a hard one to internalize, but it's true. No matter who the people involved are, or the exact situation, sometimes people will be uninterested, unreceptive, or even outright hostile. Sometimes conversations will sputter to a halt. Sometimes things will be awkward. These undesirable situations (and many more!) will happen, sometimes. Conversely, sometimes things will go really well! But it's important to be ready for things not to work out so that you won't dwell on shock or surprise, or associate making an effort with failure.

2. Recognize that stakes are low.

Going to a place that's not one of your regular hangouts and talking to a someone that you'll likely never see again means that there is nothing much at stake. Even a terrible interaction won't really have any impact outside of his memory, and so with (1) above in mind even if things go poorly on a given attempt he really isn't worse off. So there's not much reason to avoid interaction as you're not better off for having done so.

3. "Failure" isn't the only reason things might not work out.

Sometimes conversations fall flat because two people have few (or no) common interests, and so they have nothing to talk about. Sometimes people have very different styles of communication, which causes conversations between them to lean towards being awkward or disjointed. There are lots of reasons things might not work out the way your friend might hope.

This does not necessarily mean that he did a bad job at interacting with them, or that he failed in any meaningful way. Sometimes people just don't get along smoothly, and if that turns out to be the case it's unlikely that more of a relationship would be all that enjoyable for either person. It happens, and it's better to find someone whose company he might enjoy more instead of trying to force an interaction to continue.

4. You're not moving towards a goal, you are building a relationship.

This one was huge for me. Approaching a woman with the specific goal of getting a date made me feel a huge amount of pressure, in every element of an interaction, all the time. It also changes the impression that I make. It's odd to try to leap from being strangers to going on a date, and while some people can do that successfully I wouldn't bet on your friend being one of them. If my perspective is that I am getting to know someone I feel much more relaxed, conversations are much more pleasant and fun, and I'm also much more likely to determine if I would even want a romantic date with a person. And, if I do end up wanting that, it seems much more likely to happen when that has not been my goal from even before the conversation started.

5. This is something that you learn to do, not something that you start out great at.

Obviously some people have natural talent for socializing, flirting, etc. That does not describe me, and it sounds like it does not describe your friend, either. So it's important to note that if you are not as good as you would like in this area your only real option to improve is to develop better skills through practice. That means awkward starts, mistakes, and problems. But it also means fewer of those as time goes on, and more success instead. Whether or not a given interaction goes the way your friend wants, it's important to bear in mind that next time can be better.

6. You have to learn to walk before you can run.

If this situation, as a whole, is really intimidating it will be helpful to break things down a bit. Maybe a lot. So instead of having a mindset of "I'm getting a date tonight", it might be more appropriate to have a goal like "I'm going to have a conversation with a stranger for five minutes tonight". If that's still too big, maybe even "I'm going to casually smile and say hello to someone". With practice, these smaller steps can feel more natural and comfortable, providing a foundation for the next goal. My more socially-confident friends had a hard time understanding why I couldn't just follow their leads when they were my "wingmen", but I was nervous about every single part of interactions in a lot of situations. I had to practice them individually until I had enough confidence and experience to casually string them together in a "normal" interaction.

tl;dr

Without a lot of natural talent, more skill comes from practice and effort. If he's so averse to interacting with people that practicing is difficult then a different mindset is likely appropriate. With the right mindset it still takes effort, time, and the will to endure and overcome mistakes to improve. But improvement is absolutely possible.

Assuming that he does want to improve, as his friend your best move is probably to help him develop and internalize a better mindset, and then practice until his relevant social skills develop to the level he wants.

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    These are really good advices. I'd just add what @dbeer suggests, i.e. "explain to him that he's going to have to take risks [...], and that he needs to trust you.", which is also an advice I liked a lot. – Hopf Jul 18 '18 at 20:29
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I have been that guy, albeit at a younger age.

What helped me was to put me in an environment where I could get to know other people/girls in a non-sexual context, over a longer time. Picking an appropriate hobby can do that.

What also helped was taking up exercising. Helped me to feel good about my body and pushed self-confidence.

As a side remark: A friend of mine did resist all efforts to get involved with girls. At the age of thirty he suddenly showed up with a girlfriend, after everybody gave up. He picked her up all on her own, via online dating. They are now happily married and have a child. Sometimes problems solve themselves, when the time is right ...

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    He actually did this already, by going to the gym and by volunteering. It didn't seem to solve the problem, but I agree this is a very good suggestion. – Hopf Jul 17 '18 at 18:16
  • @hopf I doubt that he meant just going to the gym pushes confidence. Last year i went to the gym, but rather unsuccesfully which helped nothing. Now I (because of good diet and sport) I am at the point where I get a get a really good body (sixpack and stuff) and THAT pushes my self esteem :) – MansNotHot Jul 18 '18 at 12:45
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When helping this friend (or anyone) it's really important to gauge how much he wants helped and how willing he is to be helped. A lot of people want their problems to go away, but aren't willing to make changes that cause the problems to go away.

If your buddy really wants help, explain to him that he's going to have to take risks and put himself out there a little, and that he needs to trust you. If your buddy isn't willing to try your advice out, then he isn't willing to be helped by you.

If you really want to try to help and your friend doesn't demonstrate willingness to try things, then you have to keep trying to get him to try out different options. You could think of a few options of ways he can try to meet / befriend women and try to get him to pick one of them, for example. Maybe attempting a social pick-up is too daunting, but joining a club, taking a class, or something similar can do it for him. Keep trying, and try to help him understand that he'll have to do something.

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