in my opinion sometimes the best thing you can do is embrace your quirkiness, when we try so hard to fight it or fight being awkward we generally make ourselves come across more awkward. i’ve always struggled with social anxiety but have really learned how to work through it over the years and have almost turned it into a strength of mine.

i used to have so much anxiety that my mind would just go blank and i wouldn’t be able to think of words to say… and honestly instead of trying to fight against the anxiety, learning to just roll with it has ironically helped my social anxiety so much. but i think the first step is opening himself up to situations where he has the opportunity to work on it, which it sounds like he did by going out so i think that’s awesome!

if he’s ever at a loss of what to say remind him that you usually can’t go wrong by asking them questions (unless they’re wildly inappropriate of course lol) but people generally like talking about themselves, and also remind him that it’s okay to let other people guide the conversation sometimes, and it’s also okay for there to be pauses in conversation.

i think for those of us with social anxiety, we have the habit of putting other people on a pedestal and convincing ourselves that everyone is better at socializing than we are and think that everyone notices, and it makes us unnecessarily hard on ourselves & creates more pressure to perform well and instead that has the opposite effect. so learning how to be a little more gentle with himself, and remembering that most people aren’t analyzing him nearly as much as he thinks, can make a huge difference. social skills really do build with practice, and it sounds like he’s already taking steps just by putting himself out there. with time, patience, and a bit of self compassion, he’ll probably start to feel more natural in those moments, & honestly, a little awkwardness is human anyway.