> There was simply not much I could work with (what I thought at the time).

This has been my big blocker keeping me from talking to most people. I feel quite adept socially once I get going, but I can usually only get to that point through mutual interests or a solid conversation topic to kick off from.

I seem to usually psyche myself out because most starters feels too fake or unsubstantive. Compliments make sense, but could you elaborate on "break the pattern and make a joke, be sarcastic respectfully"?

I'll share my secret. Rather than trying to initiate a conversation with others, make it easy to initiate a conversation with you.

I started wearing hats outdoors to keep the sun off my balding head (I've had a sunburn up there, and I don't want another one), and the hat I had around to wear was from when I went as Ash Ketchum for Halloween. Or even just looking at my hat and smiling...

Nearly everywhere I go with that hat, I'll get someone saying nice hat, or professing their love for Pokemon, or asking me if I've caught them all.

This provides an opportunity for conversation and a shared interest. I can ask them if they're into the show, the books, the card game, the video games. How did they get started? What Pokemon is their favorite? Who's the best trainer? When did they start liking Jesse and James? Do they like old stuff or new stuff (I've got the OG hat from season 1).

It takes almost no effort to wear a hat and it helps me use my social skills when I'm out and about. And keeps the sun off my face a bit, and is handy for napping at conventions. You don't have to be Ash Ketchum, any character hat will do.

Also, bonus secret. When I'm sleep deprived, I get chatty... You may or may not, but if you do, use it for practice when it happens... and if you say something embarassing, you can always blame the lack of sleep. I was just at First Robotics worlds and the setup is harsh for sleep hygiene, but I had a ton of nice conversations with random robot people. Shared interest, opportunities and sleep deprivation combined. Otoh, much fewer notices of my hat at the convention center than I expected.

I was in a similar boat, but recently started getting through that barrier. The thing that clicked for me is pretty simple: I was filtering myself and chipping away at that filter made a huge difference.

For example, I was in the elevator with a neighbour and they were carrying a lot of mugs. I said "that's a lot of mugs" and we ended up having a quick conversation.

In my case at least the conversation starters are all there in my head, but I'm discarding them hunting for the "perfect" one which obviously never comes and the moment passes.

Even though typing them out may make them stupid but here are a few examples thinking out loud. Remember the body language is quite important and as you do more you start feeling more comfortable in your skin.

- Waiting for an elevator that never comes with two strangers. What I may say: I guess we'd be camping here tonight. Do you have your tent with you?

- Embarrassing moment: I hit my head lightly to something in front of 5 people: Act funny saying Oh can someone call an ambulance.

- Someone dropping yogurt from their spoon on their shirt and locking eye to eye with me realising I've been watching the moment: I would have an empathetic look and then act with an imaginary spoon picking from my own shirt and eating it.

Basically the kind of mild jokes/acts you would do and say to close people would work on strangers as well

another thing to keep in mind is that

> try to talk to someone > run out of things to talk about > feel awkward or dumb

is not really a bad outcome, physically speaking.

IMO ost people's anxiety about things X is not "fear of X" but rather "fear of fear" or "fear of embarrassment": they'll avoid something because it could go wrong and then... what? what if it goes wrong? nothing physically bad happens except that you're uncomfortable for a moment. But it's your subsequent reaction to the discomfort that is the actual source of the issue, not the discomfort itself. Which is why a lot of progress on anxiety can be made by focusing on the response: find ways of practicing being in the situation and being uncomfortable to a survivable degree such that you can learn to not be averse to the situation and can thus start adapting to it.

"I did the same thing; whoever designed these doors was a sadist." -

"Do you like that bag? I've been meaning to get a new one, I'm so tired of this one." -

"Now see, if we were as good looking/rich/smart as him we could have figured that out." -

"Is that thing broken again? I'm telling you, we're in the wrong business man." -

"Nothing to do with talent, it's a money and equipment problem, we're awesome at this." -

I've used each one of these in the past week with complete strangers, in neutral-to-unfamiliar surroundings, in passing, and the most hostile reaction I've gotten is "hahaha, I know right?" :)