Hello, regarding
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Does it actually help to challenge yourself to do these out of character things all the time? Or will I always feel this apprehension? As the years go by I'm beginning to think the technique doesn't help me at all!
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It will definitely help, but doing such things once won't fix you. One reason just 'putting yourself out there' might not be helping or giving you the results you want might be because you might not be addressing the specific things that you find difficult or
that cause you uneasiness & conversation trouble spots.
I'd also add a note about 'safety behaviours' which you might or might not have heard of. Sometimes in social situations we might believe;
-That people are always looking & noticing x
-that if people notice something about me they'll think something bad
-that if people were to comment, they'll mean something mean by it
-if people give me a hard time it's 'proof' that they're right
We might do things to try and hide how we're feeling, try and excuse our behaviour, try to avoid silences, try to justify being quiet etc. Whilst this might make us feel safe in the moment, in the long term it keeps such ideas intact in that these things may not allow us to have experiences the DISPROVE them. I don't know whether any of this is relevant to you but I hope it makes sense. Hope this helps and as others have said, this is not something that can be fixed overnight. Have patience, you'll get there.
The main takeaway is, do things that scare you, but find out specifically what's scary about said situation.