Problem [*1]:  I am a 40-year-old man who has always suffered with incredible shyness and insecurity around women. My shyness is better now; I can talk to women, and have female friends, but I have never really had a proper relationship. The few times I have had sex with women have mainly been (normally drunken) one-night stands, which haven’t been a great success as I have got very tense and been unable to perform. My loneliness and fear of intimacy is compounded by the feeling that women are going to expect me to be a lot more experienced sexually and in terms of relationships than I am. I feel embarrassed to admit my situation. I have tried online and speed dating and nothing has got beyond the first date.

1

Forget online and speed dating. Even if not by design, they end up by creating the maximum anxiety and misery for the least return.2
I think you need to be really clear what your purpose is in having a date with a woman. And what outcomes you seek.

I often ask my business clients, many of whom are golfers, ‘if you want to hit this ball into that hole, what do you focus on at the moment you hit the ball?’ Quite a few of the non-golfers say the hole—focus on the target, what you want to achieve. Almost all golfers say the ball. You focus on doing as well as you can the one thing, the only thing, that will maximise the chance of getting the ball into the hole.

In other words, the purpose of the shot is to hit the ball as well as possible, and the outcome is that it goes into the hole. So, maybe go back, if you thought your purpose in having a date, and ask yourself if, in fact, whether what you thought was a purpose was actually an outcome. The purpose drives the outcomes: if you don’t know what your purpose is, you are unlikely to achieve your outcomes.

It’s like saying “The purpose of my life is to be happy”. Well, good luck to you, let me know how it goes. However, if you make the purpose of your life to do something that is most likely to bring happiness then, most likely you will find happiness.

3
Let’s concentrate on a date. If it’s a first date and you have no purpose or outcomes for the date (“I’ll just see how it goes”), it probably won’t go far. I have learnt myself that when women go on these dates, they certainly have a purpose to the point that I feel I am on their agenda (I have literally been interrupted in mid sentence and told we have to get back onto her agenda, not in quite those words, but not far off).

If your purpose is to enjoy yourself, with the outcome that you go on a second date in the near future—apart from pointing out that ‘to enjoy yourself’ is not a purpose, it’s an outcome; it’s what happens, you hope, if you do something else—I’d say that is too selfish and the selfishness will be picked up by the woman (just as she picks it up from most other men). If, as I suspect, you’re not a selfish person, that would be most unfortunate.

A good start is to have a purpose of entertaining her. Just keep giving: stories, jokes and so on, but mostly attention. You need to prepare this (I assume you would prepare for a meeting at work). You need to go back again and again over months, years, if necessary, adding to your ‘portfolio’ of amusing things to tell people.

Most of us want to be entertained by other people, in truth. We’re all waiting for someone interesting, someone amusing to turn up, preferably before the bloke with the scythe arrives.
There are some people (women in our cases) who, to be honest, just need attention, at that moment. The capacity to ask open questions which indicate you haven’t fallen asleep will set you apart.

Focus on the date and the person with whom you are having the date. Banish all other thoughts from your mind.

4
You could try letting go of your expectations, whatever they are, good or bad.

Everyone objects to this suggestion when I first suggest it to them because they jump to the conclusion that I mean ‘expect nothing will happen’. But expecting nothing will happen is an expectation, so it too needs to be let go of. Part of the problem is that, though you think you have expectations, other people tend to interpret them as demands on them and they don’t like it (just as I didn’t like being yanked back to her agenda by the woman who expected me to stick to it). I suggest replacing expectations with curiosity. Instead of going on a date with an expectation that it will be great, or a disaster, or anything else, just be curious what might happen.

5
You need to practise.
If you have Meetup groups in your area, join some and go. Particularly the ones which are set up just to enable people to chat or interact with other people. These are almost invariably not covert dating groups, they are really just to meet others; some are more structured that others.

You need to practise. A lot.
Don’t even approach the women there with a view to a date. Just practise being more comfortable with them. You need that practice under your belt so that, when someone you like shows up, you are more confident.

[*1] My shyness and insecurity around women is still affecting me at 40 (The Guardian, 5 august 2016)

by Jeremy Marchant . image Free images
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